How To Get To $10M in ARR and Beyond Book (Notion Capital Foreword)

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Copyright © 2019. Published by Winning By Design, LLC, a Delaware Company
All rights reserved as permitted under the United States Copyright Act of
1976. No part of this book may be reproduced, used or distributed in any form
or by any means, without expressed written consent of the publisher. The
contents of this book were created in the United States of America.

Revision 2.0

Winning By Design LLC
3000 Sand Hill Road, Building 4, Suite 210
Menlo Park, CA 94025
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WHY YOU SHOULD READ THIS BOOK

This book was written for anyone who works with customers. It is based on a scientific understanding of
how revenue generation works in a recurring revenue business. That revenue generation model poses the
same questions for the CEO as well as for those in sales, marketing, and customer success: How do I
grow the business? How do I get my team to perform? Should I hire more people? Why are my customers
churning? Should I run more campaigns? Should I buy more leads? This book will give you the answers to
these questions and many more.
This book contains insights gained from working with over 300 companies over the span of four years.
Many of them are early-stage, high-tech startups but the list also contains some of the largest companies
in the world. The insights we found are the same across all of them:
1. A maniacal focus on new logo acquisition versus generating profits from existing customers.
2. The first response when targets are missed is to blame the people, not to inspect the process.
3. Absence of a uniform methodology across all roles dedicated to the recurring business model.
4. Little understanding of the unit economics that make a recurring business work.
5. Inadequate depth of basic sales skills; everyone is looking for tricks/hacks and shortcuts.
We provide simple answers to address all of the issues. With the knowledge in this book, we aim to enable
you to have a strategic conversation in the boardroom, a one-on-one talk with a 30-year sales veteran on
the changes in selling, discuss a new LeadGen initiative with the marketing manager, or coach a customer
success manager on how to upsell a customer. It’s all here. This book was written so the chapters can be
read in any order. Page through it and if you see a visual you like, dive in; that’s your starting point.

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TABLE OF CONTENTS

CHAPTER 1 INTRODUCTION 8
CHAPTER 2 ORGANIZATION 22
CHAPTER 3 THE SALES PROCESS 44
CHAPTER 4 TECHNOLOGY STACK 58
CHAPTER 5 PROFESSIONAL SKILLS 74
CHAPTER 6 SALES ENABLEMENT 90
CHAPTER 7 THE SAAS METHODOLOGY 102
CHAPTER 8 DATA-DRIVEN ORGANIZATION 126
CHAPTER 9 CULTURE 140

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ABBREVIATIONS USED
ACV Annual Contract Value LTV Lifetime Value of a customer
AE Account Executive MAS Marketing Automation System
AM Account Manager MDR Marketing Development Representative
ARR Annual Revenue MQL Marketing Qualified Lead
B2B Business to Business MRR Monthly Recurring Revenue
B2C Business to Consumer MTM Moment That Matters
BDR Business Development Representative ORG Organization
CAC Client Acquisition Cost POC Proof of Concept
CR Conversion Ratio ROI Return on Investment
CRM Customer Relationship Management SaaS Software as a Service
CSM Customer Success Manager SAL Sales Accepted Lead
CE Critical Event SDR Sales Development Representative
CEO Chief Executive Officer SMB Small to Medium Business
CRO Chief Revenue Officer SQL Sales Qualified Lead, same as Opportunity
CCO Chief Customer Officer VSB Very Small Business (emerging) segment
DEMO Demonstration WR Win ratio
ICE Impact and Critical Event

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FOREWORD

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I’m delighted to offer a short introduction to Winning by Design’s latest book, “How to get to $10m
ARR and beyond.”

When I first met Jacco in a bar in San Francisco, on a rainy night in February 2017, little did I realise
how much I would come to learn and gain from our relationship. I was struck by his passion for sales
and boundless energy, his encyclopaedic knowledge of SaaS, and his pursuit of excellence. All within
the first five minutes. If you’ve met him you’ll understand.

I was left feeling slightly dumbstruck and wondering how much of what he said about SaaS sales
strategies and models would really play out in domain expertise, insight, and most importantly in
practice. Achieving predictable, repeatable and scalable revenue is the goal for any SaaS company,
especially when venture backed. We had long been looking for an individual or team to lead a best
practice charge on this topic for us across our portfolio, someone we could consider “best on the
planet”. I knew little about Jacco, and less about Winning by Design, but I had a feeling he might be
the one.

It quickly became apparent since Winning by Design was already working with one of our portfolio
companies, Tradeshift. We had led Tradeshift’s Series A in 2010, and seven years later they were on
the verge of unicorn status, redefining the global supply chain procurement, payment, and finance
category, so I pinged a note to Christian Lanng, the CEO, who replied almost immediately...

Top line I’ve been very happy with Jacco, but the devil is in the detail, talk to Rinus (CRO).
- Christian Lanng, CEO, Tradeshift. March 2017

You know you are onto something when the CEO of a 500+ person company (now more than 700)
responds to you so promptly, so I spoke to Rinus;

I also have top marks for Jacco so far in our collaboration. As for results, he's been superb in
SDR process training and helping us model career path & role design. We'll have the full sales
team training sessions at the end of March and will have more in-depth feedback then. - Rinus
Strydom, CRO, Tradeshift, March 2017

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What I failed to appreciate at that time was both the scale of Jacco’s vision and the quality of the team
he led. Their commitment to professionalising excellence in SaaS Sales, and now Marketing and
Customer Success is backed up by a prodigious content machine that is constantly iterating the
lessons they learn from working with hundreds of SaaS companies into knowledge accessible to all.
This constant progression creates a compounding effect, just like SaaS itself, layering increased
expertise on SaaS processes, systems, tools, practices and teams on top of each other. More than
anyone else, they are leading the way for the adoption of SaaS Sales as a Science around the world.

Two years later, Winning by Design has my complete confidence and thanks and we are doubling
down on our partnership with a programme of workshops, meetups, webinars and podcasts. They are
also working with more than ten of our portfolio including DueDil, Gocardless, NewVoiceMedia, and
Tradeshift, and have influenced 50+ of our companies with the feedback having been nothing but
exemplary.

Winning by Design has been a pleasure to work with. The best integrated sales training
framework I’ve seen and a team that is smart, talented and humble. Most importantly, with
WBD we feel we have a partner aligned to supporting our long term success.
- Justin Fitzpatrick, CEO, DueDil. October 2018

Their distillation of the SaaS start-up, grow up and scale up journey encapsulated in this book, is
invaluable to us, our companies, and the wider industry. For a venture backed SaaS company
achieving $10M ARR is a major milestone, but for the most ambitious it is just step one on their
journey to redefining an entire industry. Hitting $10M ARR is no mean feat, but growing rapidly from
there to $100M ARR even more so. But with the predictability, repeatability and scalability Winning by
Design brings to a company’s growth, their probability of success is far improved. If it took five years
to get to $10m ARR, doubling every year, the science that Winning by Design brings to growth makes
a continued doubling within the realistic grasp of many, so reaching $100M ARR less than four years
later is the next step. Maybe, like Tradeshift, companies will also find their rate of growth increasing as
they get bigger! I’ll leave the final words to Rinus from Tradeshift.

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Jacco and the Winning by Design team have helped the Tradeshift sales, customer success,
and demand gen teams get "out of the box." The provocative selling techniques he has
ingrained have helped us take control of engagements and challenge prospects and customers
to focus on what's really important from our perspective." He has helped us break the barriers
of traditional demand gen waterfalls and solution selling to help fuel our 200% + YoY growth. -
Rinus Strydom, CRO, Tradeshift, February 2019

Stephen Millard, Chief Platform Officer and Partner, Notion.

xxx

Notion is a venture capital firm investing in the future of enterprise tech, in the teams and companies
that have what it takes to solve the biggest problems facing the business world, transforming entire
industries in the process. The Notion team founded, built and exited two highly successful SaaS
businesses — Star and MessageLabs, and invests exclusively in enterprise tech and SaaS with the
ambition to build category leaders. The Notion portfolio includes Brightpearl, Currencycloud, Five AI,
GoCardless, Mews Systems, Paddle, Topia, Tradeshift, Triptease, Unbabel and Workable. For more
information visit: www.notion.vc
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CHAPTER 1
INTRODUCTION

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This document contains the best practices and industry knowledge that Winning by Design has gained
from working with hundreds of startups over the past several years. It contains easy-to-understand
guidance and actions that, as founders and executives, you can put into practice right away.
THREE KEY PHASES OF SCALING A BUSINESS

Table 1.1 Key phases of scaling a business
START UP | <$1M ARR GROW UP | $1M - $3M SCALE UP | $3M - $10M ARR
The company is finding product The company has grown to $2M The company is now better
market fit with 10-20+ customers in ARR, and needs to bring in established with revenues of at
and up to $2M in ARR in its some best practices to scale least $5M ARR (50+ customers)
original market/region. The sales efforts and start thinking and with a view to be at $10M
founder(s) is still closing most about customer success to within two to three years. The
deals, leading sales and continue its growth. It has closed company should be looking to hire
marketing, has recently closed a or is in the process of pitching a specialized roles on the sales
seed round, and is working Series A of funding. team, perhaps two SDRs and three
toward an A round. to four AEs.
The company must scale rapidly
The company is ready for its first across different vertical markets. It Also needed are detailed
sales hire to start driving deals is hiring its first one or two sales processes and metrics, and
right away, to expand 2-3x in the reps, and potentially looking to implementation of best practices
next 12 months. This means hire a VP of Sales to institute into commercial teams to maintain
moving from more anecdotal formalized process, systems and competitive advantage and focus
founder sales to building a strategy for better productivity on customer retention and
professional sales team. and predictability in pipeline. expansion. It also may need to
address new markets and open
new regions to expand sales.

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INFRASTRUCTURE AND BUILDING BLOCKS FOR SCALING YOUR GROWTH

When you scale a company for growth, you metaphorically want to avoid building a 20-story building on
top of a foundation that was originally meant for just two stories. You must build a company with scale
design principles in mind. Below is an overview of these basic design principles that will enable you to
scale, compare, and leverage best practices from your fellow portfolio companies.

Table 1.2 Key elements of a Go To Market sales organization
INFRASTRUCTURE
Culture A customer-centric culture: not hard-driving selling, but rather assisting

customers through the buying process by educating them along the way
Methodology The key moments that matter along a customer’s journey, and how you
should apply customer-centric principles to maximize your impact
Data Model A baseline data model that will provide structure for your metrics, simplify your
CRM implementation, and give you a framework to compare metrics with
your peer companies
KEY BUILDING BLOCKS
Process Proven simple processes that can be implemented the right away and iterated
over time as your business grows
Technology A tool stack that acts as a force multiplier and grows with you as you scale
Enablement Training and materials provided to your customer-facing sales roles with the
latest knowledge and skills to help educate the prospect
Skills The skills required for each specialized role on your sales team for excellence
throughout the sales cycle
Organization A scalable organization that works as a team, designed to scale and prepared
for success

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Figure 1.1 The Elements of a Scalable Design

UNDERSTANDING GROWTH
Historically, growth of a sales team was based on annual revenue, and the rate of growth was fairly
dependent on the size of the sales team; doubling revenue would probably require hiring twice as many
people. However, in a SaaS model, it’s entirely possible for a sales team to double revenue without
doubling the team through growth in new customers as well as renewal and expansion of existing
customers. Many leaders have not yet grasped this model of growth, and it leads to many
misunderstandings as founders are trying to grow their companies.

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Figure 1.2 Difference between traditional sales growth and SaaS sales growth

As you can see above, the rate of growth slows down if you grow by the same amount of revenue each
year. So in order to keep the growth rate steady or increasing, it requires a significant investment in the
acquisition efforts, as depicted in Figure 1.3.

Figure 1.3 SaaS Growth Rate

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GROWTH POTENTIAL
In the B2B SaaS space, there are a lot of new factors bringing exponential growth to SaaS companies:
#1 An increase in online spend: Startups, regional
businesses and global corporations alike are becoming
more comfortable spending budget on SaaS services.
Spending $1K on one service was once thought
extreme, but today buyers are becoming comfortable
spending $5K-100K or more.

#2 A bigger marketplace: Every seller now operates
in a much bigger marketplace with technology giving
them easy access to buyers in all markets and regions.
There is an always-growing set of tools and software
that allow companies to sell from anywhere,
circumventing the traditional field sales limitations.
Figure 1.4 Where growth expectations originate

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WHEN TO ACCELERATE?
The term “growth hacking” is being tossed around

quite a bit these days. Growth hacking is essentially the
idea of figuring out a process of shortcuts to bring
more growth, faster. One of these popular shortcuts is
to use automated methods of outreach to possible
customers to book meetings, and then use low-cost
sales resources to run those meetings in an effort to
close. Initially this worked well, particularly post-2008
when SaaS solutions were becoming popular because
of their classification as Operating Expense (rather than
conventional CapEx solutions). But today, everyone
offers a SaaS/OpEx solution, and these methods of
growth hacking no longer produce the desired results. Figure 1.5 Early stages of growth

Table 1.3 Keys to scaling a business and minimizing the risk of failure
Key #1 Key #2 Key #3

Find Product-Market Fit Hit the Launch Window Execute the GTM Plan
Product-Market Fit is when a A common mistake that startups The third and final hurdle to hit rapid
mature product can satisfy a make is achieving their growth is to execute the right Go To
market, and where there there is product-market fit but waiting too Market plan often attributed to
plenty of growth potential. It’s long to scale to meet the market growing sales. It is the least
quite difficult to achieve potential, thus missing the ideal understood topic of these hurdles.
product-market fit in a market launch window. These companies will Success in executing the GTM is
where innovative solutions are become, say, #4 or #5 of the list of not measured in growth rate [%] or
launching regularly and the recommended solutions with a small revenue [ARR], but rather against
markets are never constant. sliver of market share. Today, the the growth potential within the
launch window has shrunk from market.
18-36 months down to 9-18 months
after finding product-market fit.
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KEY #1. FIND PRODUCT-MARKET FIT

One of the keys to growth in today’s
SaaS business model is to identify
your product-market fit using a
variety of sales and marketing
channels (or GTM strategies).

But here is where many organizations
slip up: they are often looking at the
overall result rather than using
metrics to measure effectiveness and
efficiency of each GTM strategy. You
might have a great product, but if Figure 1.6 Results of the lack of a GTM fit
you don’t figure out how to reach the
market through an optimal GTM
strategy, you won’t reach your users
in the market.

These are the keys to growth that you should identify while you are exploring Product-Market Fit:
● What is the value proposition that prioritizes the solution offered?
● Who is the audience that has a real problem and is willing to take action?
● How do we reach the audience with the real problem in an efficient and effective way?

Without measuring effectiveness in reaching the market, you can kick off an unfortunate downward spiral.
With no measurement, growth may slow or stagnate, the company might achieve a lower valuation than
their potential, sales leadership might turnover, and new leaders will be left trying to figure out if the issue is
due to poor product-market fit or poor sales team performance.

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KEY #2. HIT THE LAUNCH WINDOW

How do you know when you are in the launch window? There are three clear, telltale signs:

● Price increases: Instead of closing deals at $10K, you start closing deals at $15-20K ARR. This
indicates that you are offering real value and your customers are starting to understand the impact
of the value on their organization.

● Win rate increases: Win rate is measured by the number of Sales Qualified Leads (or SQLs; find
out more about metrics like this in later chapters) needed to win one deal. Instead of winning one
out of six deals, you now win one out of five deals. This is indicative of a stronger position in the
market.

● Sales cycle decreases: The sales cycle is measured as the time between an SQL being created
and until a deal is won. For example, your average sales cycle is now 71 days instead of 84 days.
This indicates that your customers are prioritizing your solution and having an easier time making a
purchase decision.

Figure 1.7 How to determine when you are in a launch window

What do these telltale signs have in common? They are data driven: They are factors you can measure,
and when interpreted correctly, can be used to make a data-driven decision.
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Don’t fall for these common mistakes, which will incorrectly lead you to believe you’re in the launch window:
● Too few deals - Your data will be skewed by a small sample size
● Not distinguishing outliers - Identifying outlier deals that are skewing your results
● Poor data entry - For instance, if you record some deals only after they close, it will skew your sales cycle to
be shorter than it actually is.

KEY #3. EXECUTE THE GTM PLAN

To achieve your maximum growth potential, you need a solid Go To Market (GTM) plan. Companies will
often secure a new round of funding to execute their new GTM: Paying for the recruitment of sales people,
increasing expenditure on marketing campaigns, attending events, and building your first custom booth at
a conference. Most organizations will use the world's most common scaling plan: Do 3x of what you were
doing that got you to this point. As you can see in the figure below, even when we grow the sales team by
3x, scaling to meet your potential can remain a challenge.

Figure 1.8 A funding round to scale growth may not result in the desired growth rate

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This is often experienced by companies that depend primarily on an “outbound” approach - reaching out
to customers proactively rather than interested leads coming to them first. These companies find out the
hard way that tripling the sales team and tripling the activities does not always triple the result. Instead, you
need a modern GTM model. Start thinking of your revenue as being composed of layers. For example:

● Regionalize teams to increase coverage and decrease dependency on your local market
● Add new products/services to uplift the price and create upsell/cross-sell opportunities
● Pursue new accounts such as moving from small business to midmarket, or pursuing new
verticals
● Add a strategic partnership that opens up an entirely new segment

Going after bigger deals is not just taking your best salespeople and giving them a list of larger target
buyers. Rather, you need to segment the market and develop a new GTM plan for that market. Recognize
that the needs for startups or smaller businesses may be different from a midmarket or enterprise
company.

Figure 1.9 Layering of revenue: each layer may need a different GTM strategy

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Table 1.4 Who is responsible for each of these areas as the company scales?
INFRASTRUCTURE START UP GROW UP SCALE UP
Culture Founder Founder CEO
Methodology Founder VP/Dir. Sales CRO/VP
Data Founder VP Finance/Dir. Sales Data Analyst

BUILDING BLOCKS START UP GROW UP SCALE UP
Organization Founder Founder/VP/Dir. Sales VP Sales+VP HR
Enablement Founder Dir. Sales + VP Marketing Sales Enablement
Skills Founder VP/Dir. Sales VP Sales
Technology Founder VP/Dir. Sales Sales Operations
Process Founder VP/Dir. Sales VP/Sales Ops

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CHAPTER 2
ORGANIZATION

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This chapter will show you how to build your sales team in a scalable way through a phased approach.

Phase 1: Start Up
In the Start Up phase, the founders are building the company and selling at the same time, likely along with
some others in the company who are also pulling double duty. If you have one founder, they are often
splitting time between building the product and trying to close the first few deals. If you have a co-founder,
or second most senior person, they are likely focusing on the engineering and delivery of the product. This
is also referred to as the ‘Mom-n-Pop’ model - with one focusing on winning customers, and the other on
delivering said product.

Figure 2.1
Co-founders (F1
and F2) are working
the entire sales
cycle themselves,
commonly known
as Founder Sales
Mode.

To explain the chart above (this chart will appear a few times throughout this book to visualize how your
sales team should evolve in each phase), here are the different milestones of the sales cycle:

PROSPECT A person who expresses interest by visiting a website or other piece of content
MQL Marketing Qualified Lead, a person who expresses interest in your product and fits the target profile
SQL Sales Qualified Lead, a person who experiences a pain that you are addressing with your product and
wants to take action
COMMIT Mutual commitment to deploy a solution that will achieve impact at a set time
LIVE Customer has been onboarded: on time, within budget and the solution can deliver impact
MRR The solution delivers impact again and again, and a recurring revenue stream is secured
LTV The revenue an account generates over the lifetime, net of churn and including growth
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In Figure 2.1, one founder (“F1”) focuses on the pre-sales motion, while the second founder (“F2”) focuses
on customer success after the purchase has been made. As you can see, it’s a lot of ground to cover for
founders.

Q: Should I hire a sales person right away?
A: No. You should close the first deals yourself. This allows you to learn what your customers
value the most in your offering. It also sets you up for longer term success. In later phases, you will
have a sales team running their own deals, but for the most strategic deals, you will be pulled in to
assist and likely meet with buyers such as CEOs and strategic decision makers. So, understanding
first-hand what goes into closing a deal will help you be more effective later on.

EXPERT ADVICE As the founder, you are your company’s first salesperson. Before you
determine who to hire, you first have to do it yourself to learn what customers respond to
and why.
DEREK SATHER
Sales Architect, Winning by Design

Q: How many deals should I close as a founder?
A: Around 20-25. Not less than 10, as these first few customers will likely be from innovators, and in
some cases, customers with whom you already have built a rapport. As such, they will probably not
provide you with real insights if the value proposition works. But don’t sell significantly more than 25 deals
yourself. You will begin to neglect your obligation to lead a growing company if you are too busy focused
on individual deals.

Q: We are a product company. Can’t I just outsource sales to a channel partner that already has
a network?
A: No. At an early stage, it is crucial that you and your team are owning the relationships with your
customers as well as learning from the selling process to understand what is resonating in your market. If
outsourced, that crucial knowledge would be difficult, if not impossible, to access through a third party.
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Further, partners simply are not going to be able to represent your product, answer detailed questions,
and give insights to your customers in the way that you can as a founder.

Phase 2: Grow Up
So you’ve now closed your first 10-20 deals and you’ve reached approximately $2M in ARR. You have
some momentum. As a founder, it feels like you are working at breakneck speed to generate leads - doing
a lot of the outbound work, speaking at local meetups and even speaking at trade shows generating some
inbound interest.

You may feel like leads are not followed up on properly, and maybe like things are falling on the floor. It’s
time to hire the first salesperson to sustain and grow from the initial sales momentum you are creating.

Figure 2.2 The founder
is doing outbound
activities, but an AE is
added to manage
inbound, and then later
to handle lead follow-up
as well. The AE will
need training and
coaching by the founder
in order to effectively
sell as the founder has
done.

The role of your first Salesperson
In this phase, you are making your first sales hire. As the first hire, they must be able to work across the
entire sales process, prioritizing and handling inbound leads, and then driving them to close (while the
founder continues working the outbound leads that he has generated). This ability for the first rep to work
across the entire sales cycle is unique! Generally, they should have at least four to six years of experience
working in your industry (and remember, sometimes this person could be one of your customers - such as
a former educator or dean of admissions). More specifically, here is what that person should be able to do:
● Prospect for leads as well as close deals
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● Understand the value of your product, and genuinely articulate the value
● Be enthusiastic about the mission of the company and what it stands for
● Be ready for change! Things change quickly and often at this stage (product, pricing, etc.), so this
person must be able to roll with the punches
● While he or she may not be building the product alongside you, they should be very familiar with
the strategy and where the product is going
● Passionate about the industry and know how to navigate it and speak the market lingo
● Easy to communicate with; you will both need to rely on each other quite a bit.
● Fun to have around! After all, this person is going to help set the tone for subsequent sales hires.
And as we will learn in subsequent chapters, culture is key.

These are things you should NOT consider to be critical characteristics for a sales hire at this stage:
● “Cuff link VP”: With several years of experience selling, you can hear the cuff links hit the table
during the interview (so to speak). This person will likely not want to do (or be good at) the
practical, hands-on work that is needed during this first phase.
● Enthusiastic go-getter: This is likely a person early in their career with an entrepreneurial spirit and
high energy. Enthusiasm is great but it can’t substitute for experience if they haven’t had sales
roles before. Having experience is critical to informing a strong sales org foundation.

Commons Questions
Q. I know a great sales rep from the past - they can sell really well, but they aren’t familiar with
my product or market. Should I hire them?
A. No. It is critical for the first hire(s) that they know the market and are passionate about what you are
trying to do. They are mission - NOT commission - driven. In the startup phase, you need people on the
team who can sell by evangelizing, educating and connecting your product with the right people in the
market. This depth of market understanding is critical at this phase. Having strong negotiation skills and a
track record of exceeding quotas does not guarantee success.

Q. How do I know if I made a good hire?
A. If the rep hits his quota but cannot implement a solid sales process, this will not lead to sustainable
growth. If he hits quota AND can establish process, then things are looking good. If he can do all of that,
AND can coach others on the team, then you’ve found yourself a great hire. Or shown another way:
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Table 2.1 Framework for identifying a strong early hire
HITS QUOTA? ESTABLISHES COACHES OTHERS?

PROCESS?
Below-average
Every now and then Not much Not happening
first sales hire
Usually, but will let you

Good Sometimes gripes about
know in advance if they will Coaches others when asked
first sales hire having to follow process
miss it
Great Establishes and improves Proactively coaches

Most of the time
first sales hire on sales processes teammates

Q. How long should I wait for my new sales reps to hit their quotas?
A. This depends if your product is an application or a platform. What we’ve seen by working with dozens
of customers is that for application-based sales, it should be 60 days for new sales reps to hit quotas. For
platform sales, it could be as long as six months.

Q. Some people have suggested that it’s best to hire two sales people at once so that you can
compare them and give them someone to work with - what are the pros and cons?
A. Well, yes and no…

If you’re hiring two sales reps (Account Executives) for the same territories at once, then no.
This tactic is an industry fairytale that usually backfires. Here’s why: At this stage, you should not be
double-hiring positions; you should be hiring the right people. Now if you want to hire two sales people
instead of one and put them in two different territories, that works. The idea of “letting them fight it out”
does not take into account that modern sales professionals should not be competing with each other,
but instead working as a team.

If you’re hiring an SDR/AE (Sales Development Rep/Account Executive) to grow together as
a team, then yes. Hiring this way to start up your sales team can help establish a good process from
the start, and finding two personalities who work well together can be very beneficial.

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Q. How do I compensate this new sales person?

A. Great question. Refer to Chapter 9 for all about compensation.

Q: What if the first sales rep wants to work remotely?
A: No. These first hires need to learn from the founders, and that means being in the room. You’re
swamped, constantly running from events to VC meetings to customer meetings, and you need to be able
to share learnings with them face-to-face for the short time that you’re actually at your desk. It’s critical
that they are able to pick up knowledge while they sit next to you, to ask you questions in real time, and to
absorb the language of the company.

Q: What if they want to work part time?
A: Potentially. It’s better to have a superstar person part-time rather than a so-so performer full-time (for
more on what a ‘superstar’ looks like, see Chapter 9). However, not just any part-timer will fit your needs
here. Most often, the successful part-timers are parents who are returning to the workplace, or people
who are returning after some kind of (productive) hiatus from full-time work. Either way, they are more
senior rather than junior in sales. If you’re hiring part time, then the profile must be someone who already
has work experience - not a first job for someone out of college.

If you decide to allow part-timers, then be sure that they come into your office when they do work (not
working remote), are working at least 25 hours per week, and are working those hours that line up with
your business. Here’s an example: If part-time means they can only work mornings, whereas your decision
makers are only available in the afternoons, then that is a problem. But with the example of returning
parents, their desired work schedule and motivations sometimes are similar to those of your existing
executives - working specific hours during the day, picking up kids after school, perhaps logging back
online in the evenings after kids are in bed.

We’ve seen part-time sales hires work quite well under these conditions . . . however, this can be really
tough to manage successfully, so consider this only for the candidates that you just can’t bear to lose, and
proceed with caution.

Q: What should I prioritize? The number of total customers or total revenue?
A. This will be a function of your product. If you are selling a platform, you are aiming for number of
logos, as the relationship between logo and revenue is linear (assuming you have a fixed price) - and
31

included in this is acquiring customers that you can reference externally. If you are selling usage, or any
other element that can increase over time, then you should prioritize for revenue growth.

Common Pitfalls

Pitfall 1: Not creating a formal price list. You may feel that the salesperson won’t be able to close
deals at the same price that you can without the deep product knowledge that you possess. To avoid this
confusion, you should formalize a price list and agree to a discount give-take list.
Pitfall 2: Allowing discounting free-for-all. Perhaps you have a firmly published price, but a variety of
discounts were applied to close the first few deals. It may feel like it has been a free-for-all. Fix this by
creating a firm discount table with defined trades (see below).

Table 2.2 Discount give-take list
DISCOUNT/GIVE ASK IN RESPONSE
5% Introduction to two prospective customers
Short use case video, tweet, or G2 Crowd

10%
(www.g2crowd.com) recommendation
15% 2-year contract, paid annually upfront, speak at an event
20% 2-year contract, paid upfront, host a workshop

EXPERT ADVICE It’s easy to want to be involved in the details of each and every deal.
But try to minimize micromanaging your AE as (s)he is pursuing a key deal. Your AE
needs to learn from successes and failures the same way you did. However if they lose a
deal, accelerate learning by debriefing together, and focusing on what can be improved.
A win-rate of 1:5 offers four opportunities to learn from.
JACCO VANDERKOOIJ
Founder, Winning by Design

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Phase 3: Scale Up

Congratulations! You have started to find your stride in sales with your first sales hire(s) in place. You likely
have some ups and downs from month to month and your numbers can still sway above and below your
monthly goal just from a large deal getting delayed. But generally, you’ve now reached around $5M in
ARR. You know that there are a ton of deals “there”, but you also know that you could be doing much
more as a company to capitalize.

You’re starting to get some inbound deals from customer referrals, but as a founder, you’re still stretched
thin trying to supplement those deals with additional inbound leads. You find that your calendar is quite
busy: you’re speaking at specialized conferences and, over nights and weekends, you’re writing blog
posts for the website.

At this point, it’s time to start creating specialized roles in sales. Clearly, you will need a few more people
to make this happen, which means that you may need a funding round. So, this is something that you
should have on your radar well ahead of time to ensure that you prepare and get input from your investors
and leadership. Once you start to create this specialization, your role as founder can start to shift away
from acting as a contributor to spending more of your time managing and leading.

Figure 2.3 The organization starts
to have specialized roles. The AE
is now focused only on closing,
you hire a CSM to cover customer
success, and you hire an SDR to
to generate and qualify leads.
Each founder manages either
pre-sales or post-sales.
33

In the previous phase, your AE was focusing on the entire pre-sale process, and one of the founders was
managing the entire success and expansion motion.

Remember, your first hire in the previous phase was your AE. In this phase, you should make the
following hires:

2nd sales hire: Customer Success Manager
Why should this role be hired so early in the growth of the team? First, the numbers prove it works: As
much as 75% of SaaS revenue comes from future years, and profitability in many cases only arrives after a
customer has been with you for more than one year. Second, you need someone to learn from what is
happening this year and help to build in best practices and improvements for the following year. And third,
happy customers will generate new customers, keep churn low, and help to massively accelerate your
growth.

Knowing that, your CSM will handle the success and expansion of your customer base: they must ensure
they are are satisfied with your product, and focus on reducing churn as much as possible. This person
might be, say, one of your existing engineers who likes working with customers. It may also be one of your
salespeople; they are often great CSM hires because they understand what customers are looking for.
Another option for likely candidates is one of your first customers, or someone you met at an event or
meetup who is really enthusiastic about what you are doing. This should be a person who is passionate
about the product and understands what customers are looking for.

3rd sales hire: Sales Development Representative (SDR)
In this phase, your AE (previously covering the entire sales cycle up until the point of Commit) will now be
overloaded with too many leads and not enough time to focus. So now is the time to hire an SDR who can
cover prospecting and qualifying leads, so the AE can focus on closing.

This SDR will follow up on inbound leads, and set up meetings for your AE. They should also help with
demand generation by inviting people to join local events then follow up on those leads as well as perform
targeted outbound on ‘low-hanging fruit’ opportunities (e.g., from trade shows). Over time, they may close
some of the easier, more straightforward deals themselves. Ideally, they should naturally grow into and
learn the AE role over time.

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Common Questions

Q: What are all of these different sales roles, anyway?
A: Here’s a summary of the roles that you should expect to have as you grow your sales org:

Table 2.3 Summary of typical sales roles
SALES ROLE QUICK REFERENCE FULL DESCRIPTION
Market Development Qualifies inbound leads, such as from your website or
Inbound leads
Rep (MDR) downloading a whitepaper
Sales Development Inbound and outbound Proactive outbound prospecting to new leads; does initial
Rep (SDR) leads, initial qualification qualification of leads prior to hand-off to AE
Account Executive
The closing role Quota-carrying reps who close sales deals
(AE)
Helps to resolve Manages relationships with customer, provides admin support

Customer Support
common issues such as password resets, etc.
Manages customer accounts, ensures that customers are

Customer Success Manages customer
successful in using your product or service, and focuses on
Manager (CSM) accounts
account expansion
Handles the onboarding process for brand new customers to

Onboarding Specialist Onboarding new
get them set up to a steady state of consumption of your
(ONB) customers
product or service

Q: Should I hire a VP of Sales first, before the AE?
A: No. A VP of Sales must be focused on setting the strategy for the broader team, as well as to help
close more complex deals. That’s where they should focus to help enable your company to scale - and
keep in mind that the compensation of a VP can be that of two individual sales roles. So we recommend
that you first establish the right roles and people to get your sales machine going, then hire a Director of
Sales - but only once you achieve Phase 4 (see below). Once you are there, hire them in a director level,
35

and then have that person earn the VP title and role. And if they turn out not to be the right fit, then hire the
right VP.

Q: Should I have my AE prospect for leads?
A: It depends. If you are selling large deals - such as selling $100K/year deals into Fortune 500
companies - and your AE has to close only a few deals per quarter, your AE should be doing the
prospecting as part of developing these accounts (networking, attending and organizing events, etc.). But
if you’re selling smaller deals (e.g., $12K/year to small or mid-market businesses), and your AE has to
close 3+ deals each month, he won’t have time to prospect in addition to working his opportunities. So it
now requires a series of additional skills, such as outbound email and cold call techniques. Here you will
need a two-stage sales cycle, where either a Sales Development Rep (SDR) performs the prospecting
activities, or a marketing campaign generates inbound leads that the AE can follow up on.

Common Pitfalls

Pitfall 1: Not enough leads are generated. If that’s the case, then one of the following is happening:
a) You are too early: Focus the SDR on organizing and creating a database of the right contacts to
target.
b) The SDR is not the right fit: They are not spending their time in the right ways. This role is highly
activity based, and the SDR must put in the time to conduct a certain amount of each activity. As a
general benchmark, it takes about 50-100 emails, 10-50 phone calls, and 10-100 profile clicks
every day in order to generate the necessary number of leads. Sit down with your SDR and AE as
a team and see how they feel about the progress.

Pitfall 2: Too many “fluffy” meetings. A lot of educating is happening on the calls, but leads are not
entering the sales funnel. Spend two to three hours per day with the SDR, and help them understand how
to prioritize and better qualify leads. Spend time coaching them on a few calls, and reviewing outbound
emails and responses to inbound.

Pitfall 3: Deals are not properly handed off. The SDR must provide a smooth hand-off to the AE. This
includes making a proper email intro between the lead and the AE, as well as providing the AE with the
right level of information. The AE and SDR should be meeting regularly (once a day) so that the SDR can
provide background on the person, what they are interested in and why, and any other relevant points.

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Pitfall 4: There seems to be a lot of interest, but nothing is getting closed. This could be happening
for a few different reasons:
1) It’s an early market that has not yet fully developed. If that’s the case, be sure to stay
hyper-focused on prospects who have a pain (a problem to solve), rather than everyone who is
simply interested in your space.
2) You have long sales cycles. In certain industries, buying may generally happen in a certain time of
the calendar year. If you miss that window, that could mean a full one-year delay. If that’s the case
for you, be sure that your sales team is hired six months before that window opens.
3) Poor lead qualification or poor execution by your existing reps: Check that your existing team has
the necessary industry knowledge and sales skills to be successful. See Chapter 5 for more on
Skills.

Understanding the Infrastructure You Are Building
As you progress through the three phases of Start Up, Grow Up and Scale Up, you must start to think
about how you want to set up your sales organization to scale beyond that point. Every company will be
slightly different depending on your product and business model, but there are a few proven best practices
and organizational structures that you can rely on, depending on your needs.

Best practices for a scalable sales organization

● Build your sales org in a phased approach; don’t try to hire entire teams all at once
● Organize your team into PODs, where each team has a specialization
● Decide if you are going to specialize geographically (e.g., New York, Los Angeles) or per market
segment (e.g., by vertical):

➔ Specialization based on geography is best for solutions that require salespeople to go
on-site, and/or to have a strong relationship within the community. This most commonly
involves high contract value selling, to the likes of large enterprises.

➔ Specialization based on vertical is best for specialized solutions selling into a market that
requires specific knowledge and insight; think of selling to financial institutions versus health
care companies. Traveling to each customer would be expensive, so sales reps in this
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model will often rely on online selling, supplemented with an in-person customer tour
(anywhere from monthly to quarterly).

● Clearly define roles for each member in the POD, such as: Account Executive, Practice Advocate,
Customer Success Manager, Inside Sales Manager, Sales Manager, Customer Success Team
Lead
● Define how Sales will interact with other parts of the company. For example, Sales and Customer
Success will work in concert on renewal vs. expansion sales. Another example: you should
determine how and when Sales should provide the Product team with customer feedback and
feature requests.

Example: Phased approach to a scalable sales organization

Figure 2.4 The organization starts to specialize as
inbound vs. outbound to support deal flow. As
you start to run out of leads, SDRs need to
develop and work campaigns in tandem with
Marketing. On the other side of the customer
journey, Customer Success starts to get
overwhelmed by onboarding requests and isn’t
spending enough time helping customers get the
most value from the product with consistent
usage.

When this applies: Below $3M ARR
Figure 2.5 The organization now starts to

specialize in onboarding vs. customer success.
The Success team is helping customers use the
product, and is renewing monthly/annual
contracts. But upsell activity is lagging, in
particular from the big accounts that you had high
hopes for. Your net revenue increase barely
covers the churn.
When this applies: ~$3M ARR

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Figure 2.6 The organization starts to specialize in
deal size (most common) OR vertical markets. You
will find that you can scale using this model. You
will need VPs of Sales and Customer Success to
manage these specialized motions and
challenges.
When this applies: ~$5M ARR
Organize the team in a POD
How does a POD work? In the example on the right, a 2x2 Figure 2.7 The
POD is shown in which an MDR (Market Development Rep specialized
focusing on inbound lead development) and an SDR (Sales roles are
mapped into a
Development Rep focusing on outbound lead generation)
POD
are partnered with two AEs. The MDR/SDR combo sets up,
say, 40 meetings for the AEs each month. From these
meetings, the AEs might close eight deals per month.

Why do PODs work well, and why should you use

them? Team work, accelerated learning, motivation, mutual
accountability. High velocity is based on proper deal
handoffs.
How to model a POD. Historically, the efficiency of these PODs was not considered an issue due to
more focus on winning logos rather than achieving profitability. But starting in 2014, the tides turned as the
number of SQLs per SDR dropped from 20-30 on average to low 10s. Today, we know that for a POD to
be economically viable, the annual on-target earning (OTE) of this POD should not exceed 40% of annual
revenue. E.g., to generate $1M in ARR you should not exceed spending $400,000 in compensation; this
includes base salary AND commissions.

39

Table 2.4 POD Modeling
EFFICIENCY SPECIALIST POD Base+Variable=OTE METRICS DESCRIPTION
MDR 500 MQLs

(Inbound) 1 $40K+$10K=$50K 5% Conversion rate
25 SQLs (I) per month
SDR 1 $50K+$30K=$80K 15 SQLs (O) per month

(Outbound) 40 SQLs (I+O) per month
Jr.AE 1 $80K+$30K=$110K 20% WR Wins three deals per month

$10K ACV
Sr.AE 1 $100K+$40K=$140K 25% WR Wins five deals per month
$12K ACV
ONB 1/2 $50K+$20K=70K 8 Customers onboarded/mo
(Onboarding) $96K ARR per month
TOTAL 5 $415K $1.162M ARR generated / yr

Table 2.5 Example of different POD models and common uses
STANDARD INBOUND OUTBOUND TARGET

Used for a regional Used with an inbound Used with an outbound Going after a few
approach, or large business where lots of approach, often hand-picked accounts
vertical market - e.g., inbound leads are platform sales, with a valued $50-250K ACV
one for the West coast generated - often with a high ACV of $12-50K with a dedicated team.
and one for the East low ACV of up to $12K
40

How to grow PODs? As your revenue grows, your PODs will start to multiply. Each POD is responsible
for a dedicated revenue flow. The more PODs you set up, the more stable your revenue growth becomes.

Figure 2.8 Visualizing how your sales org scales over time

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How to use PODs to run sprints to identify target markets? One of the key advantages of PODs is
the realization that you can quickly refocus your resources depending on the market; this is very important
during the early days of scaling revenue. In the example below, you will notice the specialization over time -
we call these sprints. The POD will heat-check specific verticals/regions/segments. This allows each POD
to train only on the needed use cases/value proposition for each sprint. The sprints can vary in length,
anywhere from 30 to 90 days.

Figure 2.9
This shows the use
of PODs to
heat-check a
market by sprinting
through a series of
verticals, such as
regions or market
segments

Example of how to structure a sprint over time:
● First two days: Train the team on use cases, and role-play a variety of scenarios
● First week: Pursue B-leads first to get familiar with responses, meet up and share best practices
● Second week: Market and organize an event, pursue your A-leads to attend
● Third week: Pursue A-leads, host events, follow-up with event attendees
● Fourth week: Wrap up, learn from best practices by measuring what worked, start next sprint

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How to scale your staffing? We have found that PODs also allow you to scale your recruiting. Meaning,
a new POD can be launched by promoting the top performer of an existing POD (e.g., AE of POD 1) to
become the new POD leader of POD 2. The team leader of POD 1 can backfill the position within the POD
and hire a new MDR.

Figure 2.10
Stabilizing the
growth of your
sales team: the top
producing POD 1
does not get
disrupted while
POD 2 is being
built. POD 2 is built
from the ground up
with a top leader
that sets the stage.

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44

45

CHAPTER 3
THE SALES PROCESS

46

Let’s start by creating a very simple sales process. Different sales teams may use different words to
describe the steps in their process, but the generic process below covers the vast majority of all sales
processes out there. Notice how this process is customer friendly, in that the activities are described from
the point of view of customer value - not from the perspective of a sales person trying to hit quota.

Figure 3.1
Standard
Customer-Centric
SaaS Sales
Process

In this sales process, you can see three different areas:
● Prospecting (in red), with three sources of opportunities: Outbound, Inbound and Targeted
Accounts
● Sales process (in blue), with the classic steps of your conversation with the customer
● The beginning of the Customer Success process (in green)

Not every Go To Market model needs the exact same sales process. In fact, there should probably be
slight differences between them depending on the segment or type of customer. In the table below, you
47

can see how sales activities across the sales process can vary, depending on which type of target is
concerned.

Table 3.1 Applying the sales activities
CLIENT VSB/ SMB/ MID-MARKET/ ENTERPRISE
ProUsers Teams Departments
Methodology Transactional Solution Consultative Provocative

(sales cycle) (secs/mins) (days/weeks) (weeks/months) (months/quarters)
Prospecting Inbound Outbound Target Identify
Hand-off CRM CRM + Email 1:1 Meeting 1:1 Meeting
Impact/Critical Decision
Diagnose Provoke
Event Process
Custom
Prescribe Workshop
Demo
Standard Demo
Decision Proof of
Assist Trial
Criteria Concept
Business
Recommend Quote Proposal
Case
Trade Buy Trade Negotiate

P/O
Commit Online Contract + SoW
Go Dark Nurture Outbound Alerts Provoke
Onboard Enable Install Integrate Onboard

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How to Create Your Own Sales Process & Sales Playbook

No matter what stage your company is in, you must have a clearly defined sales process and playbook.
Success in SaaS sales requires measurement, and measurement requires that you be methodical. So
creating your documented sales method allows you to: 1) provide consistent guidance to your sales reps
on how to progress through their deals, 2) conform your activities to a process that you can easily
measure, and 3) understand what’s working and what needs adjusting.

STEP 1. DETERMINE WHICH SALES PROCESS
Determine the sales process best suited for your business from Table 3.1 (make modifications as needed)

STEP 2. MAP OUT THE STAGES
Map out the stages of your Sales Playbook. See Table 3.2

STEP 3. DEFINE THE STAGES
For each stage, you should define the following:

● Goal: Description of what needs to happen at that stage
● Actions: A few simple actions per stage that the sales rep should take in order to get clear insight
into the customer situation
● Enable: Enablement tools available to assist the process (documents, references, team members
to bring in)
● Outcome: The single outcome that should result from the actions taken (often a confirmed
meeting)

Now let’s see what you should keep in mind depending on which of the three phases your business
currently falls under.

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Table 3.2 A snapshot of a generic SaaS Sales process

Stage 3
Stage 1 Stage 2 Stage 4 Stage 5
PRESCRIBE
HANDOFF DIAGNOSE ASSIST RECOMMEND
(NEEDS
(QUALIFICATION) (VALUE PROP) (PROPOSE)
ANALYSIS)
GOAL Secure a meeting Diagnose the pain, Navigate the org Assist the Create a proposal
with a prospect identify the urgency and keep customer through outlining price and
who fits the and determine if educating by the decision impact it will have
profile and has a you can help them. providing materials. process. on the prospect’s
pain. business.
ACTIONS 1. Prepare 1. Prepare 1. Decision 1. Decision 1. Propose

- SDR handoff - Research Makers Criteria - Develop proposal
- Call before the situation - Identify Decision - Identify Decision - Schedule review
call - Identify process criteria call
- Situational Use-cases 2. Educate/Demo - Identify impact of 2. Orchestrate
questions 2. Have Meeting - Top three Pain each criteria - Set up a refer call
- Pain questions 3. Discovery Points 2. Decision - Involve execs
2. Confirm - Get Critical event - Ballpark pricing Process - Involve Customer
Situation - Establish Impact 3. Drive a - Hierarchical or Success
- Situational decision consensus?
questions - Establish a 3 x 3 - Chronological
- “Did I get that steps
right?”
3. Determine
Pain - Emotional/
Rational
ENABLE - WBD Research - WBD Discovery - WBD Demo - WBD Decision - WBD Proposal
- WBD QCards - WBD Account criteria
Plan - WBD Decision
Process
OUTCOME Scheduled a Scheduled a Scheduled a Scheduled a review Proposal sent and

discovery meeting custom demo decision criteria of the proposal reviewed; schedule
meeting with review meeting meeting with buyer
decision makers
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Phase 1: Start Up

In this phase, it is unlikely that you have a CRM and are probably storing sales activities on a spreadsheet.

Figure 3.2
A simple “solution” sales process
to use as a baseline while in the
Start Up phase

Commons Questions

Q: When should I start creating my first process and playbook?
A: After the first 10 deals. Update it after 20, 30, 40, 50. Then it should be stable up to about 100 deals.

Q: How many stages should my process have?
A: No more than 10. Remember not to over-engineer a process; that’s the enemy of a sales rep’s time.

Q: Should I start from scratch?
A: You could for the first 10 deals, but why? We provide a proven template for you to work from (see
above) that has been created based on the learnings from hundreds of companies that came before you.

Commons Pitfalls

Pitfall 1: No process. In Founder Sales mode, you keep winging it. Every deal closes differently. To you,
it’s pretty clear but to others, it’s a mystery. So how do you establish your first process? Do a search
across your email and calendar for the customer’s name and root name. This provides a history of how the
51

relationship was started and meeting you had. See if you can glean some themes or common language
across these deals.

Pitfall 2: Self-centered process. Looking at your sales process, it feels sales-y (e.g., “Qualify, Demo,
Negotiate,” etc.). It may seem like semantics, but reps absorbing guidance like this will add up to a
company that wants something but gives little - and ultimately will have unhappy customers. The best way
to solve this is to look at the key actions in each phase and ensure they provide real value to the customer.
For example, instead of “Qualify” say “Diagnose” and then teach your team how to diagnose the
customer’s pain by asking the right kind of diagnostic questions. Qualifying, on the other hand, will often
be more focused on determining the customer’s situation, and it won’t help the sales rep get to the
customer’s true underlying issues.

Pitfall 3: Overly detailed process. Over-designing a sales process will kill deals. You don’t need to
identify every step and criterion. That will soon translate into dozens of fields to be completed in your CRM,
and before you know it, your sales reps have basically turned into accountants and are spending little time
talking with customers.

Phase 2: Grow Up

In this phase, you’re outgrowing the spreadsheet and you need to implement your first CRM before things
get out of control. Your CRM at this stage can be something like HubSpot (free) or ProsperWorks (G
Suite-based). You may not be willing to commit to something like Salesforce quite yet, as it often requires
a significant amount of time and resources (usually a Salesforce consulting partner) to set up.

52

Figure 3.3
Scaling up the
sales process to
focus on outbound
and become more
customer-centric
Commons Questions

Q: Should I just get Salesforce already?
A: No, use a simple CRM to start. We recommend holding off at this stage. Right now, your process is
not 100% set yet because there is still more to learn as you build up your sales team. You need flexible,
simple tools that are easy to manage at this stage; see Chapter 4 on Technology for more details. Learn
from those before you: For every change that you need to make to Salesforce CRM, you often need to
make many others. Talk to anyone in Sales Ops who has implemented SFDC at their company, and they
will tell you that it gets real involved, real fast.

Q: Should I hold my team accountable for executing the process?
A: As much as possible, but as little as needed. You need to be flexible to change. Review and
update the process every quarter to make sure that it’s still meeting your needs. Use recordings (calls,
demos, etc.) to streamline the process as much as possible.
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Commons Pitfalls

Pitfall 1: You are not analyzing your deals against a process. You keep winning deals, but you’re not
going back to learn why the customer bought your solution, how you can continue to replicate that, and
how you can improve their experience.

Pitfall 2: You are hiring a sales rep and think they should be able to do it. Your first sales person will
have experience in sales, but likely doesn’t have much experience building a sales process from scratch.
Sit down together for a few hours and build the sales process with your sales rep in a Google
slide/doc/sheet. Your knowledge of the customer plus the rep’s knowledge of efficient sales will both
contribute to a better process.

Pitfall 3: You are selling to several different types of customers. At this stage, it is important to really
focus on the type(s) of customers that you want to want to serve. For example, if you are still selling to
everything from individuals to global companies, then you are quickly going to see that your resources are
spread too thin. You will run the risk of doing a mediocre job serving too many segments, rather than an
excellent job knowing and serving a more focused customer segment. Be sure that you have become
purposeful and consistent in determining your target users that you want to serve.

Pitfall 4: You are closing deals but not providing any support post-sale. Customer success
post-sale is just as important (if not more so) than the sale itself. If you don’t yet have any dedicated
Success team members, make sure you work out a plan with your product/engineering team for how to
address customer issues that come up.

EXPERT ADVICE Avoid exporting the data to a spreadsheet or slide and using that for
reporting. Both for internal meetings with your team and for board meetings, you should
use reporting from your CRM. This may take a bit more time in the beginning to get used
to it, but it avoids days of chaos and panic the week before the board meeting, as you’re
getting your numbers straight from the source.

JACCO VANDERKOOIJ

Pitfall 5: You’re using the wrong process. In general, when a prospect reaches out to us on our
website, we respond with a series of actions. These include: Call them, leave a voicemail, send an email.
We know time is of the essence, and many companies aim to do these actions within minutes. But what
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we found is that this time-sensitive approach is often used in the wrong situation. To clarify: A prospect
downloads a detailed research paper on your website by providing their email address in a form. This type
of lead is often wrongly categorized as an inbound MQL. But the SDR calls the person immediately, leaves
a voicemail and sends a follow-up email, as if the prospect has already expressed a pain. But they never
did! The prospect feels intimidated by the assertive follow-up. So clearly, not every inbound lead (MQL) is
created equal. This MQL should have gone into the outbound process where research should have been
performed to determine if this prospect has a pain.

Figure 3.4
Fit and Pain are reversed on
inbound vs. outbound processes,
resulting in the wrong action

Table 3.3 The difference between “true inbound” and “quasi-inbound” leads
TRUE INBOUND QUASI-INBOUND
● Talk to sales ● Download an online asset

● Schedule a demo ● Sign up for a webinar
● Contact us ● Visit the pricing page of the website
Being quick is the most important. Being relevant based on research is more important
than being quick.
Next step: Inbound Process. Next step: Outbound Process.

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Phase 3: Scale Up

In this phase, you need to get your process and CRM secured.

Figure 3.5
The process adds
targeted account
outreach, which is
often associated
with provocative
selling. In this
phase, the sales
process now
extends to
customer success
for a full
customer-centric
relationship with
each account.

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This is a time to invest in doing it right, as you are now building the platform that you will use to scale. Your
metrics need to be locked and dashboards ironed out. You may also realize that you are now addressing
new segments, such as selling to mid-market from only SMB before. Each of these new markets need to
go through the same development of your sales process: Win your first 10 deals, then establish a process,
then update the process with the next 10 deals, up to 50 deals, and so on.

Common Questions

Q: Should I create a different process when I sell into a different segment? If I use one sales
method (consultative) to sell to SMB and I am moving up-market to sell to larger companies, should I
change my sales process?
A: Yes, most likely. Selling to mid-market is a very different sale in that it requires more people to
approve the process, the sales cycle is often longer, and they have a more structured purchasing process.
You will need to adjust your sales stages, timing, and tactics at each step so that you can add value in this
new type of process.

Q: Should I just get Salesforce?
A: Probably. You should also discuss with your peers in your specific industry or niche market to learn
what they have seen.

Q: What should be on my CRM dashboard?
A: We have created a sample dashboard in the Annex for you. Use that to get you started.

Q: What should I spend on a CRM/process consultant?
A: Somewhere between $5K-10K to set up your CRM and create dashboards. They will need to know
your process, so make sure you have your playbook ready.

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Common Pitfalls

Pitfall 1: You keep the same sales process. Don’t make this mistake. New segments behave
differently from others and you need to continue being customer-centric by making your sales process fit
each segment.

Pitfall 2: You want to set up your CRM yourself. Yes, of course you’re capable, but this is not the
time. If you’re setting up SFDC, you should bring in a proven SFDC consultant who can help you get it
right the first time, and avoid redoing it (and all of the headaches that come along with that) later on.

Pitfall 3: You want to use a niche CRM. Commit to a standardized CRM that provides the best
infrastructure. The extra unique customization that you might get from a niche CRM doesn’t even come
close to the benefit that you get from installing a CRM that is easy to use and familiar to your sales reps
and sales operations.

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59

CHAPTER 4
TECHNOLOGY STACK

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The tool stack that you choose to use is just as strategic as the organization and the processes that it
supports. And it can get overwhelming very quickly. There are literally thousands of options to choose from
for all of the various tools your team will need.

In general, we see two common options:

AN SFDC-BASED INFRASTRUCTURE A GOOGLE-BASED INFRASTRUCTURE
Using Salesforce as a CRM, with all of the SaaS Using tools based on G Suite (Google products)
services available in the Salesforce App Exchange. with their apps on it. G Suite is commonly used
This sales stack is most commonly used by with early and high velocity solutions. Companies
companies that have an Annual Contract Value of that sell applications (rather than platforms) tend to
$15,000 or more. Often a platform product, and use a G suite infrastructure for longer before
often longer sales cycles that need a robust switching to SFDC.
toolset.

Luckily, there are a few key guidelines that you should follow that will help narrow down the field to point
you in the right direction toward an effective tool stack.

#1 Know the difference between the layers of the stack
● Server: You need servers for the operations of your business. In general, the major players you will
be selecting from are Microsoft, AWS and Google.

● Platform: Once you choose a platform, recognize that it can be tough to switch in the future. So
be sure to do your research on platforms and ensure that you choose those that will allow for your
dependencies. Think of Salesforce, Hubspot, Marketo or Zendesk.

● Application: Applications can be stand-alone, fully integrate into your platform, or work
side-by-side. Applications can be exchanged more easily if your business needs change and grow.
Think of Calendly, Bill.com and Zoom.

● Outsourced Services: These are external services that will perform an entire function for you.
Think of an outsourced SDR, or an outsourced lead enrichment service.
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#2 All tools should contribute data to the database
Since many of your decisions in the future of your company will be data-driven decisions, we want to make
sure that all tools contribute data to your knowledge base. Take the example of an email automation tool.
Instead of asking sales people if they are effectively using email, make sure you are using an email tool
where you can simply see the answer with data. Meaning...your email automation tool automatically logs
all inbound and outbound emails, and produces response and deliverability metrics for those emails. In
general, even if a specific tool is functionally better than another, we recommend that you keep looking if it
does not contribute actionable data to your collective organizational database.

#3 Contracts with different types of technology should be treated differently
● Servers: The infrastructure you are building on. This commonly is either Microsoft or Google server
infrastructure.
● Platforms: After an initial one year contract, you should feel comfortable to strike a multi-year
commitment if the platform suits your needs
● Applications: Use a maximum term of 12 month agreements, and renew annually
● Services: These should have contracts based on usage or impact; make commitments of no more
than three months at a time

#4 All functions need to be supported by tools, but be sure to keep it balanced
Every function needs some amount of tooling in order to scale. But take care: it’s easy to load up the
marketing department with many tools while customer success has less support. Be sure to avoid this.
The more tools you have, the more manpower you need to manage and administer those tools, as well as
interpret the data and insights that those tools provide. Make sure that you strike a balance between tools
and human brain power.

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Recommended Sales Tool Stack

One of the questions that we are asked most often is, “What tools should I buy? I don’t want to go
through a long vetting and selection process. Can you just tell me which ones are good?” The answer to
that is - it depends. It would be very easy to point to the ‘best’ tool for lead generation or the ‘best’ tool for
proposal creation - but that simply wouldn’t be serving the needs of your business. Why? Because the
needs of every business are different. This is why there are so many tools out there that all have different
capabilities and feature sets.

With that said: We can’t say that the tools listed below are the “right” ones for everyone. This list is meant
only to be a starting point - a gauge to help point you in the right direction - so that you can evaluate other
tools from there and make a selection based on what fits with your business. And keep in mind that new
amazing solutions are cropping up all of the time, and point solution tools get acquired by larger
companies every year, so this list is by no means conclusive or exhaustive.

For some great resources and further details and tool reviews, check out:
● The 2017 Startup Sales Stack Report from Bowery Capital
(https://bowerycap.com/blog/sales/2017-startup-sales-stack-report/)
● Sales Hacker Best 160+ Sales Tools: The Complete List, 2018 Update:
https://www.saleshacker.com/sales-tools/
● G2 Crowd Sales Software reviews: https://www.g2crowd.com/categories/sales

But before we get into the details, let’s set the high-level baseline first for what is needed in each phase of
growth.

Phase 1: Start Up
In the Start Up phase, you have only a couple of sales reps. You don’t need to overburden yourself or
them with too many tools. The guideline here is to do as much as you can with simple spreadsheets, and
supplement with just a few hard-working tools: you should enable prospecting with tools like LinkedIn
Navigator, MixMax and Calendly, and for most other tools, you can use manual/spreadsheet substitutes.

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Figure 4.1 Most startups use Google G Suite to start building their tool stack: it’s easy, relatively low cost, and
strong in sharing capabilities.

Google G Suite: Provides cost effective access to classic office productivity products. You will quickly
become addicted to the ease of their products and the ability to share, edit, comment and collaborate in
real time. You will start to play around with your first applications that can operate on top of or integrate
with Google G Suite:

● ZoomInfo: Over the next few years, you need to build a high quality database, which means that
you need to use high quality inputs. ZoomInfo provides reliable contact information for your target
prospects based on the parameters that you set.
● Drift*: As you are building up visits to your website, you should start engaging with those visitors.
Drift allows you to chat with them. Here you can use the Drift bot to quickly answer questions,
book meetings and gather insights. We recommend that you implement this as early as possible
(freemium version).
● LinkedIn*: Rest assured that LinkedIn for both understanding who you are meeting with, as well
as lead generation, will be a reliable and valuable source of information.
● MixMax*: As you are getting your sales team started, you will need to do a lot of scheduling,
sending templated emails, and a bit of email cadences. MixMax offers all of this in a very
user-friendly way, so that you can be incredibly efficient with your email outreach.
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● Zoom Conference: While in-person meetings are incredible valuable, it won’t help you scale to be
where you need. So start to use and get comfortable with remote meetings via video conferencing
with Zoom as quickly as possible.
● HelloSign/DocuSign: You need to maintain an electronic record of your electronically-signed
documents and agreements from day one. Use a freemium subscription until you are exceeding
the amount of free signatures, and then move to a paid subscription. We recommend that with
whatever provider you choose, stick with it for at least a few years.
● Xero: Don’t attempt to send your first invoices manually; just immediately start using Xero. The
complexity of doing this manually and the mistakes that occur with financial transactions simply
aren’t worth the small amount in savings. See below for an example of a customer-friendly invoice.
Note that this early stage is the time to give your direct phone number so that you can resolve any
financial issues quickly.

Hello <First Name>,

Thank you for your business, it means the world to us! Please find invoice <invoice number> for <invoice
amount> due on <due date>. You can view your bill online here: <insert link>

If you have any questions, please do not hesitate to contact us.

Thank you from all of us at <Company Name>.
<Your Name> | <your telephone number> | <your email address>

Common Pitfalls

Pitfall 1: Commiting to payment/contract terms that are too long. We strongly recommend that you
first go with monthly, even if it is more expensive. If the tool proves to be impactful, then move to an
annual/upfront contract. Do not agree to auto-renewal!

Pitfall 2: Jumping right into paid subscriptions when a free version is available. This is the time to
test and learn. There will be plenty of other tools that you will want to buy over time.
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Pitfall 3: Not using a tool for critical tasks such as document signing, or web conferencing.
These are critical tasks that you should not execute with free tools.

Pitfall 4: Buying into a CRM/MAS right away when you don’t even have 10 customers yet. Don’t
invest in an expensive subscription before you need it. Also, consider that you will need someone to
implement and manage a CRM - it doesn’t just run itself!

Phase 2: Grow Up
In the Grow Up phase, you will have outgrown your heavy reliance on spreadsheets. Here you should
implement a lightweight CRM, enhance your lead qualification with lead enrichment and analytics, and
start to use the paid versions of some of your tools, rather than just getting by with the free versions. You
will quickly see how the extra spend will be worth the efficiency gains as you scale.

Figure 4.2 In the Grow Up phase, Marketing Automation and CRM platforms come into play in your tool stack.

You’re growing, so now is the time to commit to your first platforms:
● HubSpot/Pardot: Use this for your Marketing Automation system so you can build landing pages,
track content engagement and manage your first “newsletter-like” campaign
● Pipedrive: This is a popular CRM system that easily plugs into your Google infrastructure, though
some may prefer to stick with Hubspot and use their CRM solution

You are moving from freemium subscriptions to paid subscriptions:
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● Drift: Start using playbooks per page (includes campaigns, qualification and scheduling)
● LinkedIn: Pay for the premium subscription (Sales Navigator); it provides advanced lead search
and lead recommendations
● Zoom: Move to a paid license and start investing in a proper ‘Zoom Room’ (Zoom-equipped
conference room with integrated audio and content sharing). No more kitchen table or bedroom
video conferencing!

At this phase, you may find yourself starting to use your first outsourced services:
● External Accountant: It is probably time to have an accounting firm perform your invoicing and
chase down payments. You can now hire a qualified external accountant who logs into your Xero
account remotely, and immediately take that burden off your shoulders.
● Lead Enrichment: In the first phase, you were surfing websites, LinkedIn profiles, and
government sites to find leads - all of this can be outsourced. An easy way to hand this off is to
create a screen recording with a voiceover where you show and talk through how you generate
these leads, and you can outsource it by finding a person on a platform such as Upwork. Give the
person you hire the video so that they can see exactly what they should do.

EXPERT ADVICE There are a few helpful ways to make an Upworker successful. First,
record a short video or detailed write-up of the work you want them to do. Next, outsource
the work to three to five people on Upwork who meet your experience and location criteria,
and review their work after a paid trial period. Hire whichever person did the best job. Solid
work product plus excellent communication (both style and responsiveness) will be present

in the best candidates.
SARI EISENDRATH
Sales Enablement, Winning by Design
Common Pitfalls

Pitfall 1: How to decide on a tool? There are basically three areas of impact from a tool set:
1. Be more effective: win more deals (think of tools such as Infer or Everstring)
2. Be more efficient: do the same amount of work with less resource (for example, Calendly)
3. Have a better experience: There are two different points of view:
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a. Customer has a better experience: Think of Docusign and how easy it is for the customer
to execute a document
b. Improve the operator experience: Think of a tool that helps people avoid having to
endlessly enter data - such as an accounting tool like Xero, or a quotation tool like
Pandadoc
If a tool provides impact in all three categories, GREAT. If in two, GOOD. If just in one, it better be one
heck of an impact to justify purchasing it!

Pitfall 2: You are not sure how to choose, there are so many options for tooling. A/B test over a
period of one to two weeks, then choose.

Pitfall 3: You pick an excellent tool, but it doesn’t integrate with your existing stack. Don’t do it.

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Phase 3: Scale Up

In the Scale Up phase, you will now have a sizeable sales team, and you will need a more robust toolset to
enable your team and orchestrate more sophisticated activities. This becomes very important now that you
will be adding more sales reps at a much faster rate compared to sales operations/enablement and sales
managers. You should be implementing tools that can provide sophisticated insights and enable you
across the full customer lifecycle.

Figure 4.3 In the Scale Up phase, you should introduce a customer database and upgrade to industry-grade tools

Platforms: You need to implement the infrastructure that will likely stick with you until $50M ARR. So
choose wisely!
● Customer Database: Use Salesforce. It’s expensive and it can be cumbersome, but it’s the most
scalable.
● Marketing Automation System: Inbound companies (applications) often pick HubSpot, whereas
outbound companies (platforms) often pick Marketo. You need a platform that provides detailed
data on amount of leads, where they came from, how they engaged with your company and what
content they have consumed.
● Customer Relationship Management: Use Salesforce (see above).
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● Customer Platform: You likely will use a combination of Zendesk (ticketing) and may add
Gainsight or Totango on top of that for customer success.

EXPERT ADVICE One of the keys to picking the right tool is determining if it integrates
with your data model. For instance, is a call recording automatically added to the customer
record in your CRM, or does the sales rep need to do that manually? Look out for these
seamless integrations to complete your data model.
JULIE WEILL PERSOFSKY

Applications: You likely now have several different teams with different needs and different asks for the
applications they want to use. You need to start prioritizing what deserves your investment.
● Cloud-based proposals: Build proposals, add terms and conditions, and use real-time updated
customer lists with a tool like PandaDoc
● Cloud-based phone system: You can no longer just be an “email company with cell phones” so
it is time you put in a phone system, 1-800 line, etc.; use a cloud provider like TalkDesk or
NewVoiceMedia
● Real-time dashboards for board-level reporting: It is time to stop driving your organization
crazy at every board meeting; instead, use reporting directly from standardized dashboards, using
a solution such as InsightSquared
Outsourced Services: At this point, you can add extra services to cover your weaknesses. Some of
these use their own tools:
● Call reviews/coaching: To improve sales performance, you can start using a tool such as Chorus
or Gong, which will record calls and provide call analysis. These services directly integrate with
Zoom calls. To analyze the recordings, you can work with an outsourced service such as Winning
by Design to perform call reviews for you - ensuring your sales metrics such as ACV, win rate and
sales cycle are in the top 10 percentile.

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Common Pitfalls

Pitfall 1: How to avoid an overload of tools? Any tool that involves a multi-month contract should
require approval from your executive team. This is important, as every tool requires an investment from
your team of time, training, budget - or a combination of all of these.

Pitfall 2: It is so easy to load up on tools...how many SaaS tools is right?
Note: Numbers below are the for entire company, not just for the sales organization
● Start Up: 10-20 tools
● Grow Up: 20-30 tools
● Scale Up: 30-50 tools

Pitfall 3: Loading up on tools without having enough manpower to run them. You will need at least
one (if not a few) people who are dedicated to Sales Operations to manage your tool stack. As easy as
these providers make it seem that you can just plug and play, you will need someone to manage the
process of vetting, running pilot tests with your sales reps, selecting, integrating, and managing.

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With all of that said, here are even more granular recommendations for each type of tool in each phase.

Table 4.1 A starting point for tools to think about about at each phase of growth.
Note: (G), (M),(S) indicates where a tool is strong with G Suite, Microsoft, or Salesforce, respectively.
START UP GROW UP SCALE UP
Account-Based Sales & Marketing
Social selling platform: Must have Sales Navigator is nice Sales Navigator is a
LinkedIn to have must have
Analytics
Reporting & business Spreadsheet CRM built-in InsightSquared

intelligence dashboards
Communication / Conferencing
Internal office collaboration Slack Slack Slack
Contact center/phone Your own cell phone Your own cell phone TalkDesk/New Voice
system with Google Voice with Google Voice Media
Conference calling/online Zoom (Basic/free) Zoom (Pro) Zoom (Business)

demo
Call recording & analysis - Apple Quicktime Gong, Chorus, or

Refract
Online chat: Drift Free Standard (custom Pro (bot play books,
greetings) auto CRM)
Content Sharing & Management
Collateral management G Suite G Suite G Suite

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[CONTINUED] Table 4.1 A starting point for tools to think about about at each phase of growth.
Note: (G), (M),(S)
indicates where a tool is strong with G Suite, Microsoft, or Salesforce, respectively.
Contract Lifecycle Management
Proposal creation G Suite G Suite Pandadoc
Document execution Freemium product DocuSign (shared DocuSign (group

(HelloSign) license) license)
Contract & billing Xero Xero Xero
Customer Relationship Management (CRM)
Customer Relationship Google Sheets(G)/ Hubspot Free(S)/ Salesforce/

Management (CRM) Pipedrive(G) Pipedrive(G) Pipedrive(G)
Customer success DIY Build into the Gainsight/Totango

product (e.g., insert
Intercom)
Marketing automation - Hubspot Hubspot/Marketo
Support ticketing - - Zendesk
Lead Generation / Productivity / Prospecting
Prospect identification/lead intel ZoomInfo ZoomInfo ZoomInfo
Online lead generation LinkedIn LinkedIn LinkedIn Sales

Navigator
Lead enrichment DIY Offshore Offshore
Predictive analytics & lead scoring - Infer/Everstring Infer/Everstring

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[CONTINUED] Table 4.1 A starting point for tools to think about about at each phase of growth.
Note: (G), (M),(S)
indicates where a tool is strong with G Suite, Microsoft, or Salesforce, respectively.
Predictive analytics & lead scoring - Infer/Everstring Infer/Everstring
Outreach/Prospecting MixMax(G) MixMax(G) MixMax(G)

Outreach(M) Outreach(M)
Salesloft(S) Salesloft(S)
Productivity
Calendaring Calendly (Basic/free) Calendly (Premium) Calendly (Pro)
Sales & Market Intelligence
Competitive intel Owler Owler
General
Server Infrastructure (Mail, G Suite G Suite G Suite

Calendar, Drive, etc.)
Build a tool stack Not really Start doing it Must have it;
formalize it on a
poster

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CHAPTER 5
PROFESSIONAL SKILLS

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Many founders make the mistake of thinking that the team in place from the very beginning will be the
same team they need when the company grows into a billion dollar company.

Each phase of the company requires different skills. This is of course not to say that you need a different
team at each phase - your team members can certainly grow their skills with the needs of the business.
But founders must think about how to recruit for the current phase, and also look ahead to the next phase
and the potential business and skill needs.

These are the high-level qualities and skills, by phase, that you should be looking for and recruiting in
candidates:

● Start Up: Self starter, reliable performance, proven superstar, might dislike process, will help to set
the tone of the culture you are looking to establish
● Grow Up: Loves to create a process and document what they are building, able to listen and learn
from what goes around them, enjoys working with and learning from small teams
● Scale Up: Team performer, love to execute process, dependable nine-to-fiver, might need a bit
more hand-holding and likes processes ready-made so that they can go execute on them

Just as important as performance is the cultural fit. These are skills that cannot be trained (or would require
way too much of your time).

Some questions to ask yourself regarding cultural fit when meeting with candidates:
● Do they work hard? Do they have a track record of working hard?
● Are they able to identify and solve a problem rather than just pointing them out to their manager?
● Do they take notes? This is a great indication of candidates who are trainable and have the ability
to execute a process.
● Do they clean up after themselves? This often is a great indication of team player.
● Do they ask questions? Do they seem genuinely curious about your business?
● Do they have experience that relates to your product?
● Can they communicate with you? When you walk to get a cup of coffee with them, do they start
the conversation or do you have to drive the communication?
● Do they display high intellect, and do they seem to enjoy using it to solve problems?

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5.1 How to Recruit

Develop four to seven criteria (e.g., empathy, curiosity, sales skills, diligence) that your hiring team will
gauge all candidates on, and make sure that the entire hiring team understands exactly what is meant with
each criterion. Schedule a time for the hiring team to meet after every interview loop to discuss the
candidate, but only after you’ve asked everyone to submit their feedback using an online form, as this
avoids groupthink. Even if it’s a clear ‘yes’ or ‘no’ from everyone, still meet and talk about WHY: This may
lead to some interesting learnings, as sometimes small items will emerge as trends across all of the
interviews, and perhaps even adjusting your criteria or process for how you interview.

Table 5.1 Methods of recruiting for each role
START UP SCALE UP GROW UP
METHODS OF ● Word of mouth ● Dedicated recruiting ● In-house recruiter +

RECRUITING ● Personally recruiting firm that knows your candidates via
people in your own culture recruiting firm
network

During a period of active hiring, you may want to consider setting aside an entire day for nothing but
recruiting. Recruiting is very disruptive to the company flow. The most common example? It will occupy a
lot of your conference rooms!

Here’s how this would work:
● Block conference room(s) for the whole day. Make sure they are clean ahead of time (clean the
whiteboard, etc.). This is best done on a Thursday (you’ll see why below).
● Notify your front desk/EA/shared space lobby that you will have several candidate guests, and
provide their names.
● Set 30 minute interviews each, with 30 minutes of overflow at the end in case it runs long. Those
who are identified as rock stars should meet with the CEO/VP immediately after their interviews.
● CEO/VP should block the whole day for “email” so they can interview potentials right away.
● Offers for each job requisition should be pre-approved internally, so that you just need to add the
candidate’s name to it.
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● Candidates who make it past the CEO interview are asked to perform a role-play/task the next day
(Friday) on-site (or online if they do not live in the area or their travel plans do not permit). For the
role-play, they can sell their own material, or they can use your standard deck.
● Have one person on your staff coordinate the candidates and process in a master tracking sheet.

Even during periods when you’re not focused on hiring, you never know when you will run into someone
who is the perfect fit - perhaps your Uber driver, or the barista serving your coffee. So be sure to have
‘recruiting business cards’ always on hand you can pass out. You can use your regular business card, or
think about printing a different version that says “I think you would be a great fit, and we’re hiring!”

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Here are a few great exercises you can ask candidates to perform during an interview.

Table 5.2 Role-play exercises to use when interviewing candidates for each sales role
MDR/SDR AE CSM DIRECTOR
EXERCISE - Role-play an - Role-play the - Draft the agenda for - Have them create a
outbound cold call opening of a an onboarding call forecast for $10M
- Write an outbound conference call on the whiteboard in revenue
email - Role-play an online - Role-play an - Role-play how they
- Chat with me via demonstration onboarding call would coach an
text message as if - Build a pipeline: How - Role-play a call with underperforming
you are in a chat on many deals, a frustrated rep
the website meetings, and leads customer - Ask specific details
- Find 10 prospects are needed for you - Demonstrate how of how they coach
using with LinkedIn to perform you orchestrate the team beyond in
and talk through - Role-play negotiating bringing a new 1-1s and “on the
why they are good a contract customer floor”
prospects stakeholder up to - Develop a forecast
speed using ACV, sales
cycle, conversion
rates, and churn
- Design your sales
dashboard for the
leadership/board
SKILLS TO You want to see You are looking for the You are looking for You want to see
LOOK FOR excellent verbal and candidate’s ability to how they interact in structured thinking,
written control the situation. different mediums, positive but firm
communication skills. their ability to stay coaching, and ability
calm, and control the to motivate in
situation with the best negative situations.
customer experience
possible.

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Best Practices

Recruiting is not just done by you...involve others, even if they are not obvious. For example, inform the
front desk manager, regardless of whether they work for your company or for your shared office space.
Ask the front desk for their feedback on how the candidate interacted with them (were they friendly,
dismissive, etc.). And never, never hire a candidate who is disrespectful or dismissive to anyone on the
team - regardless of role or seniority. That is a culture cancer that can easily be avoided.

Just don’t listen to what candidates say, but observe their behavior. Here are a few common ways of
identifying behavioral traits that we have found to be extremely important:
● Do they take notes? For instance, in the first interview, the interviewer can state the five key things
you are looking for in this role. An hour later, have another interviewer ask the candidate to repeat
those five things. If the candidate doesn’t remember what they were, do you think they will
remember to take notes of the key criteria on a customer call?
● Do they clean up after themselves? Offer water to a candidate. Upon leaving the room, notice if
they clean up after themselves. Many team cultures are based on the idea that “everyone does the
dishes”, so figure out if the candidate would blend in with that environment.
● Are they honest and sincere? Throughout the conversation, gauge the person’s level of interest. Do
they seem truly curious and genuinely interested in your company and this role? Are they asking
you questions that are thoughtful and applicable?

None of these by themselves should be a disqualification, but as a whole, it should provide a story.

Common Questions

Q: Should I use a recruiter?
A: Early on, you should hire people you know. However, once you enter “Scale Up” mode, we
strongly recommend that you adjust your strategy.

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Table 5.3 Recruiting strategies, by phase

UP TO 10 EMPLOYEES 11-25 EMPLOYEES 25+ EMPLOYEES
Do your own recruiting via your Seek out people on LinkedIn and 25-49 people:
network of trusted people. write personal notes from the Develop a relationship with a
Founder/CEO to ask them for a trusted recruiter who knows your
coffee. culture. They should help with
open positions, but also keep an
eye out for great candidates and
always send them your way.
50+ people:
Consider an in-house recruiter.

Q: What is the best way to use an external recruiter?
A: Invite them over to your company. Explain the culture to them and who you are looking for. Ask for
their help, what is possible, what compensation levels they recommend, etc. A good recruiter can provide
you with job description, pay analysis, titles, and more. But always remember that recruiters (especially
sales recruiters) are primarily sources for candidates. They can not interview your candidates and do not
typically provide much more depth than finding the right “type” of candidate, usually based on a resume
screen.

Q: Should I pay the recruiter a retainer?
A: Only for executive positions, and only once you have reached at least ~25 employees. If less
than that, you should still be searching through your own network and through VCs.

Common Pitfalls

Pitfall 1: Hiring people only when you need them. You may say “no” to a great person because you
think you don’t need them yet. In rapid growth mode, we can always make great people work. Are they
open to a more flexible role until everything sets in? If yes, then make the hire.

Pitfall 2: Your recruiting process is built around candidates. While in Scale Up mode, you may find
you are interviewing a lot of people, and you do it per their availability. This is causing massive disruption to
your company because you are unable to find deep focus time to get work done. Instead, organize a
recruiting day per week/month. Then properly prepare the organization, block a meeting room for the
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entire day, and clean up the office to make a good impression. If needed, hire someone for the day to
manage the front desk. A few key tips:

● Inform your recruiter and ask for their help to fill the calendar. They will be interested, as this makes
for a very efficient way for them to find quality candidates for you.
● Recruiter performs initial screening calls with the candidates. The hiring manager performs 30
minute interviews on a Thursday, with 15 minute overflow + 15 minute reset. If a candidate
appears qualified, they are walked into the CEO/founder’s office for a 15 minute chat. Qualified
candidates are asked to come in the next day/online for a 60 minute group interview by the
executive team.
● An offer is made by Friday afternoon after you’ve done a back-channel check with a trusted person
using shared contacts.

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Figure 5.1
Sample calendar of
a recruiting process
for a company
during Scale Up
mode

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5.2 How to Onboard New Employees

You’ve managed to get through the tough part of finding great employees. But stay on point! These
employees need guidance and training before they can start producing. You probably don’t have the time
to run a full onboarding program every time you bring on a new hire group, but there are ways that you
can make it easy on yourself. And yes, you must have some kind of onboarding program. Don’t just put
new reps on the phone their first day! They’re not ready!

A few guiding principles here to get you started:
● Onboarding isn’t just the first week or two. It’s just a reality that humans can only handle so much
new information at once. Reinforce over time, with different methods (classroom, hands-on, etc.).
● Onboarding and training new team members should be the responsibility of the entire company.
Be sure that your existing team knows that training new hires is a worthy investment of their time
and energy. The better prepared they are, the better and faster they can start contributing.
● It’s crucial that new reps hear about the company strategy directly from you and the rest of the
leadership. This sets the tone, clarifies where the company is headed and why. That’s a message
that should be delivered directly from the source, not passed down in a game of telephone.
● A common mistake in onboarding sales reps is not making them get close to the product,
especially if you have a technical product. Don’t let this happen to you! A portion of their training
should include working with customer support. Some companies even have a requirement for
every employee to spend a few full days per year doing customer support.
● Create a buddy system: Every new hire should be paired with an existing employee who they can
shadow, and who can show them the ropes.
● Your onboarding program should get better every time you run it. Get feedback from your existing
team AND the new hires on how the program went - both immediately after, as well as a few
months after once they have settled into their spot. They will have some great perspective at that
point on how to improve the program.

Here’s a sample onboarding program that you might use for your first few reps that you bring on to the
team.
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Table 5.4 A four-week enablement plan for a startup (e.g. the first rep)
WEEK 1 (DETAILED PLAN) WEEKS 2, 3, 4 (GENERAL GOALS)
● Day 1 AM: Welcome from the CEO/founder. Week 2:

Intros and icebreakers. Discuss the vision and ● Attend an online event/webinar/conference.
goals of the company. Team/welcome lunch. Become familiar with the industry.
● Day 1 PM: Set up IT/laptop/desks. Go over the ● Learn three customer use cases by heart.
top deals that were won, talk through why each ● Practice pitching (record a video of yourself)
customer purchased. with a friendly audience. Focus on having a
● Day 2 AM: In-depth product demo by the conversation with them rather than presenting.
founder. Record it! Understand the ‘why’ behind ● Sit in on as many customers calls as possible
how it’s done. ● Meet with the person installing/onboarding your
● Day 2 PM: Pipeline conversation with the key service, discuss what is working, and what is
members of the team. Talk through goals, and not working
the path to get there. ● Review/get sign-off on 30/60/90 day plan.
● Day 3 AM/PM: Visit a few customers together
Week 3:
with the CEO/founder. Take close note of how
● Perform three customer calls with the founder
your service is positioned. Debrief at the end of
shadowing; discuss feedback after the call.
the day.
● Start getting on the phones full time: Make 100
● Day 4 AM: Establish a simplified sales process
phone calls this week (150 next week).
(use this guide) and get a list of content (content
map) that the CEO/founder is using to educate Week 4:
and wow customers. ● Two or three day road trip to apply what has
● Day 4 PM: Present and role-play with the been learned; this can be an event or
founder until you get it right. conference.
● Day 5 AM: Role-play again with the founder.
● Day 5 PM: Draft a 30/60/90 day plan. Record everything you can! Watching and
reviewing your work is quickest way to ramp.

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As you move into the Grow Up and Scale Up phases, your onboarding needs will be very different than
when first starting out. See below for a more extensive sample onboarding plan that would be used in
these later stages of growth. With a variety of speakers and modes of learning, the entire company is
helping to train new hires.

Table 5.5 A four-week enablement plan for onboarding new reps in Grow Up and Scale Up
WEEK 1 (DETAILED PLAN) WEEKS 2, 3, 4 (GENERAL GOALS)
● Day 1 AM: Welcome from the CEO/founder. Week 2:

Intros and icebreakers. Tour of the office. ● Start to master the pitch, and get coaching from
● Day 1 PM: Set up IT/laptop/logins/tech/ senior sales reps.
badges/desks. Take care of HR paperwork. ● Know the basics of using CRM.
● Day 2 AM: Company vision/strategy. In-depth ● Mastery of the industry: Self-study using
product demo. resources to get up to speed on industry
● Day 2 PM: Presentations from the rest of your trends.
executive team, covering their vision, overview ● In-depth presentation from Marketing team.
of their team, and how they work with Sales. Understand sources of lead flow, types of leads,
● Day 3 AM: Team with engineering/customer marketing events, programs and partners.
support to answer customer support inquiries.
Week 3:
(amazing way to quickly learn the product and
● CRM mastery
understand the voice of the customer!)
● Review quota, compensation and territories
● Day 3 PM: Start shadowing their buddies. They
● Heavy on call shadowing
should watch their buddies using CRM, listen in
● Role-play customer calls with different scenarios
on calls, shadow everything they are doing.
and use cases
● Day 4 AM: Sales process overview. Training on
● Pass your pitch certification by presenting to
how to use CRM and include basic training plus
sales managers
overview of customization.
● Day 4 PM: Practice asking questions to identify Week 4:
customer pains in small groups. ● Start getting on the phones if certified
● Day 5 AM: Continue buddy shadowing. ● Create territory plans
● Day 5 PM: Diagnosis practice: Each new hire ● Evaluate their readiness; determine if any
runs through how they would diagnose a knowledge gaps still need to be filled
customer’s pain.
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5.5 Training Specific Skills
Regardless of role or skill level, keep in mind that there are a few core principles that EVERYONE on the
team should be doing:

Table 5.6 Customer-centric selling principles
#1 Pain #2 Emotional #3 Educate #4 Assist Buying #5 Value

NOT Fit BEFORE Rational DO NOT Pitch DO NOT sell in every interaction
Do your research Emotional impact Trust that if you People hate being Don’t just do
and only reach out benefits people, educate the sold, but they love to check-ins. Instead
to those who have rational impact customer that they buy. Stop the selling; provide value in
a pain, not to benefits corporations. will make the best instead assist people every interaction with
those who are a fit! Focus first on the decision. who want to buy. every customer,
emotional impact. every time.

Building on those principles, there are certain core skills that each person in each role must have. See
below for a breakdown of these basics. And as a reminder, this diagram shows how each role comes into
play in the early phases of growth.

Figure 5.2 The key sales roles across the sales cycle

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Table 5.7 Core skills to master at each sales role. For each of the core skills labeled as Moments, see Chapter 7.
The Sales Director role should be able to perform all of the skills, but should focus only on the ones indicated.
CORE SKILLS MDR SDR AE CSM DIRECTOR
Communication (Moment 1) x x x x x
Prospecting (Moment 2) x x x
Conducting discovery (Moment 3) x x x x x
Diagnosing the issue (Moment 3) x x x
Establishing a critical event x x x
Assisting the decision process x x x
Recommend - Conducting a demo x
Overcoming objections x x x
Trade (Moment 4) x x
Commit/Close x x x
Onboard/Orchestrate (Moment 5) x
Use/Achieve Impact (Moment 6) x

Upsell/Account management
(Moment 7) x x
Coaching x
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CHAPTER 6
SALES ENABLEMENT

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A little enablement goes a long way. You can kick start enablement for your team with the following:

1) A content journey of what material to use/when: As a founder, you know exactly when to use
an article, a blog post, or even a tweet. How do you get your team to do the same?

2) A few key hardworking enablement templates: These are assets that are dead-simple to use,
and perfect for completing together as a team and using in coaching exercises.
a) Qcards
b) Bingo cards
c) Sales Playbook, Prospecting Playbook, Customer Playbook
.
3) ‘Posterized’ design and best practices for processes:
a) Sales process
b) Tool stack

In the early phases of growth, if you and your team spend just a little bit of time and effort to set up a
process for documenting the knowledge base that you already have and what you collect over time, then
you will quickly have a robust content library that you can use for ongoing learning and training new reps.

Table 6.1 Types of enablement needed at each phase
START UP SCALE UP GROW UP
Content Journey Spreadsheet (10 items) Spreadsheet (20+ items) Content Map
Enablement N/A QCards Bingo cards

Sales Playbook (two SaaS Method Playbook
pages)
Design N/A Customer Journey Tool stack

Sales Process

Content Journey
As a founder, you are probably quick to draw on a wealth of articles that you’ve read over the years,
quotes from books, and blog posts you keep as a reference. This helps you as you work with your
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customers, so send them this information when you feel the time is right. But as you scale the company,
this kind of knowledge needs to be archived, updated and shared. The way to do this is by building a
content map.

Figure 6.1 Example of a content map used for a company in Grow Up phase - work towards this!

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Horizontally across the content map, you see the journey your customer goes through (as will be explained
in Chapter 8 on Data). Vertically down the map, the customer goes through four stages:
1) People first do research and understand the problem
2) Shortly after, they look for and research the solution
3) They look for a way to see it work in action
4) Then they take an action: download something, click on trial, or start to chat on the website

As a customer learns, they use the next level of content. Take for example, “Seeing It Work.” The customer
isn’t interested in committing to a two-hour whiteboard session; they’re just looking for a quick video. But
the level of commitment increases as they progress through the experience and become more invested.

Table 6.2 An example of a type of content across the customer lifecycle
MARKETING PROSPECTING WINNING STAGE ONBOARDING USING
“Seeing It Youtube video Online demo by Sign up for a trial Mutual commit to Demonstrate
Work” an SDR or AE a proof of concept real case
study

Now, the amount of content that you have created in the Scale Up phase will be much different than the
amount you have available in the Start Up phase. But at each phase, you can easily keep track of what
you have and how it should be used. Here’s how:

Table 6.3 An example of how to start an early-stage content library that everyone on the team can use
TYPE OF PHASE WHAT IT’S USED FOR SPECIFIC POINT
CONTENT
eBook Marketing Shows the customer the types of solutions that are Page 3, second
available paragraph
Trend report Marketing Shows the customer what trends they should think Page 12
about applying to their business
Checklist Winning Shows the customer what they need to do in order 3rd item
to implement a solution like ours
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Enablement Templates
QCards
Qcards are a quick reference guide that sellers can keep on their desk and easily reference at any time.
The format is 5x8 cards, bound by rings, that sellers can flip through to quickly find the information they
need in order to prepare for discovery calls. They include overviews of buyer personas, dives deep into
their mindsets and emotional/rational pain points, and frameworks for preparing for discovery (see
screenshots below).

Figure 6.2 Sample of QCards describing Customer Profiles to allow sellers to sympathize with their prospects

Bingo cards
Play bingo with your team! Record each type of customer call, and use these bingo cards to have your
team listen for each of the elements of the conversation, checking them off as the call progresses. After
the game, discuss how the call went and how the sales rep performed in using the call frameworks.
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Figure 6.3 A sample Bingo Card, used to reinforce the sales process

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Process chart
A sales process chart summarizes your sales process: The goal of each stage, the actions you should take
in each stage, and the criteria for progressing through the process. Following a strict sales process is the
cornerstone of a successful sales team.

Figure 6.4 An overview of the entire sales process, available as a poster (Mimeo) or template (LucidChart)

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Sales Playbook

Figure 6.5 A 1-page Sales Playbook template

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Best Practices

There are a few proven best practices that you can employ in order to quickly build a robust enablement
program and content library for your team. Putting in just a little bit of time to make this happen will provide
rewards for your team tenfold.

● Create a library of:
○ Content for each stage of the sales cycle: Create a spreadsheet with links, by stage, to
each asset (this should be no more than 20 assets). Set a regular schedule for updating the
assets, and involve your team in rotating ownership of this.
○ Successful prospecting emails: Open a shared doc and have your team members paste a
copy of their best performing prospecting emails.
● Learn from your wins: With every new win celebration, interview the sales POD on the same set of
questions for no more than five minutes: Talk about who they worked with (show the customer’s
LinkedIn profile), how they came to us, what was their critical event, what was the impact, who did
we compete with, what was the trade-off.
○ Record the interview and then create a QuickQuiz. New reps should listen to the interview,
and then fill out the QuickQuiz. The QuickQuiz should contain questions such as:
■ Look up the person on LinkedIn and find descriptive traits that will help to
understand this person’s mindset (e.g., “was the first to innovate” within a peer
review).
■ Fill in the critical event, impact, etc.
● Identify your buyer’s process: Have each team member pick out one of their customers that they
would like more of (i.e., a model of an ideal customer). Each person should do a root search in their
email on the company domain name (e.g., acme.com…). Look for the first several emails that were
exchanged, and discuss what trends and insights you can find from that process such as: What
was the value prop that was discussed? What was the language used?
● Develop your talk track: Have each rep record a random call. Meet with them individually to review
the call, and then have the rep present what she did really well and what can be improved for next
time. Create a training/onboarding module from this that you can use for new hires.

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Commons Questions

Q: Do I need some kind of tool to manage all of this content?
A: Nope. Once you hit serious critical mass with a sales team (global team of 50+), then it may make
sense to use an enablement tool. But until then, your effort and budget are better spent by keeping it
simple with some well-organized spreadsheets.

Q: These templates are cool, but I don’t have the time to fill all of these out.
A: You shouldn’t! Do a workshop with your sales team across a few Friday afternoons, two hours each
Friday, when you get together in a room and each start filling out an asset. Rotate to check each other’s
work a few times, and before you know it, you will have the beginnings of your enablement content library.

Common Pitfalls

Pitfall 1: Letting enablement assets get stale rather than setting aside some time to keep them
updated. In the early phases, it’s not yet necessary to have a dedicated enablement team member. So
this means that before you hit that point, your sales manager must build enablement into the
responsibilities for the entire team. They should set up a regular cadence for reviewing templates, updating
materials, and building in more best practices. Involving team members is key here: Get one rep to spend
30 minutes helping with this each week.

Pitfall 2: Build enablement into team goals in some way. This is an undeniable way to ensure that the
entire team understands the value of enablement and takes ownership of it. There are lots of ways to do
this: Make it a part of their overall compensation, provide spot bonuses for great contributions to the
content library; feel free to get creative with it.

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CHAPTER 7
THE SAAS METHODOLOGY

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The goals of the blueprints we provide are simple: Create a framework, not a script. Each blueprint will
show how to perform a set of actions during a Moment That Matters. Each of these frameworks can be
improved as your process is refined until they work at their absolute best. But before we share some of
these blueprints, we want to provide a guideline that we have found to be critical in today’s sales culture.

Your interest in helping a customer resolve their problem must be authentic. It cannot be
manufactured, and you should not use authenticity as a “trick” to close a deal. More and more marketing
organizations are making authenticity a concept: they recommend to use of certain words, record videos
on your LinkedIn, etc. We do not believe this is sustainable. If you master the five principles below, you will
be genuinely authentic - not because it helps you close a deal, but because during the process of
executing these principles, you have become someone who cares.

Principle 1. Understand their pain
Do your research and only reach out to those who have a pain or whom you think you
can help avoid it. Do not reach out to people who are “just a fit!”
Principle 2. First emotional, then rational
Humans make decisions emotionally, and then justify rationally. Focus first on the
emotional impact.
Principle 3. Educate through storytelling; do not pitch
Trust that if you educate the customer, they will make the best decision. Therefore, help
your customer think through the problem they are experiencing, and share best
practices of others who experienced the same.
Principle 4. Assist the buying process
People hate being sold, but they love to buy.
Principle 5. Provide value in every interaction
Don’t just do check-ins; provide value in every interaction with every client, every time.
Offer market information, insights, use-cases and whatever else you can to add value.

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We have identified the Moments That Matter, and aligned them along the impact journey of your customer.
Next, we are connecting each moment to a corresponding conversion metric (for more about these
metrics, see Chapter 8). We can now provide a series of examples of specific actions your
customer-facing teams can take during these moments to improve the respective conversion rates at each
moment. And as you will learn in Chapter 8, a small improvement in conversion rates at these moments
can have a big impact on revenue.

Figure 7.1 Key Moments That Matter, the impact journey, and the corresponding conversion metrics.

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The seven key moments we are going to focus on are:

1. Reach out based on a pain they may have, be relevant to them from the first moment
2. Have a conversation as a human being, not a sales qualifier
3. Perform a diagnosis on the customer’s situation before you prescribe a solution
4. Trade, not negotiate: maintain value for your product by trading items of equal value
5. Orchestrate, not onboard: redo the deal once the customer is signed
6. Achieve impact, not pursue usage: look for both the emotional and rational impacts
7. Grow in different areas: Renew, up-sell, re-sell, and cross-Sell

Moment #1: Reach out to customers who have pain

When we ask our customers who their prospects are, they often mention a job title in a vertical market,
such as the CTO at a financial institution. Many companies buy, and/or create a list of prospects that hold
a specific title, in a particular vertical market, and are in a certain region with a specific size. They then
enrich the database with email addresses, telephone numbers and social handles. This will only lead to an
ineffective outreach email like the one in the next example.

Dear <First Name>,

I noticed on LinkedIn that you are the {{ job title }} at {{ company name }}. The reason I am reaching out
to you is that others in your industry such as {{ first name }} at {{ company name }} ran into {{ problem }}.

Attached a {{ use-case }} that describes how {{ our company name }} helped him/her solve this by
{{ doing this }} and how it {{ caused xx% increase }}.

Can we meet for 15 minutes to discuss how we can help you?
<Close>

Figure 7.2 A personalized yet INEFFECTIVE outreach email.

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The thing about this email, which is quite representative of today’s sales organizations, is that it is the
result of correlation, rather than a trigger event.causation.

When we ask the CTO why they signed up for our service, we learn that it was because earlier in the year
they suffered a security breach. The fact that they were a bank was pure coincidence and thus correlated
with their profile, but not caused by it. What that means is that for this seller, any other institution that had
a breach should be a prospect, regardless of it being a bank!

This allows us to rewrite the outbound email based on a trigger event - referencing the customer’s true
pain point - instead of just based on correlation.

Dear {{ First Name }},

In your recent article you mentioned that your infrastructure was breached.

Please find attached a use-case from two weeks ago. On page two, I highlighted how the headaches of
a similar breach can be avoided based on a best practice discovered by {{ first name }} at {{ company }}.

{{ First name } }, let me know if you like to talk to one of our experts on this?

<Close>
Figure 7.3 A personalized, EFFECTIVE outreach email that is based on a customer’s pain.

Reaching out to a prospect using a provocative statement takes some preparation. Here are the steps you
can use to define the provocative statement for each prospect:

Step 1. Pick one of your own accounts and perform research
Step 2. Pick a value prop and use-case that applies most to the customer (the person, not the
company)
Step 3. Research the current situation through online search as well as phone calls to employees
Step 4. Outline specifics of the new situation without overtly mentioning your products or terms
unique to you
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Step 5. Identify a critical date such as a product launch, or an event such as “reaching 1M users”
Step 6. Establish rational and emotional impact based on a selected value prop; ensure you have
a use-case (proof) of a relevant customer (size, location, market, etc.)

Figure 7.4 Blueprint of a provocative statement

The caveat here is that we all receive dozens of emails a day that provide no value. Even the cold
outbound email we described in the example above may soon be a thing of the past if they become too
templatized and no longer relevant. Low email open rates are already taking their toll on outbound
campaigns worldwide, and that is even if those campaigns are well written and based on a prospect’s true
pain, as we recommend.

Moment #2: Conversation, not qualification

One of the first things all salespeople are taught is qualification. This is the task of determining if a person
representing a company with characteristics - such as size, market, and intent to purchase - qualifies them
to continue in the sales process.

When sales professionals were selling IBM Mainframe computers, this made a lot of sense. There were
only a few mainframes to go around, and everyone wanted them. However, the cost of selling entailed
tens of thousands of dollars with access to specialized resources, such as engineers and architects, that
provided their expertise around integration into the customer’s infrastructure. Sales had to use a defined
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set of questions to extract concessions from a customer and based on the answers, determine if this was
a priority for the seller. In today’s world, a SaaS solution can be integrated into a cloud platform with a
single click or the provision of a login via an email. Outdated qualification methods designed around
multi-million dollar products do not apply to high velocity sales. The customer has lots of options, and
budget is not generally a problem.

Figure 7.5 How to apply TALKER conversation techniques to initial customer calls

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So instead of qualification, we recommend building conversational skills to establish the priority and the
impact the customer is looking to achieve. The framework for teaching conversation skills is built on an
easy to remember acronym, TALKER:
Step 1. Tone of voice, not just in the use of an actual voice, but the use of emoticons in chat
and email. One of the key elements of tone is speed - for example, not being too fast in
person, but responding very fast in chat.
Step 2. Ask questions. Master not only closed- and open-ended questions, but also learn to ask
diagnostic questions like a doctor would.
Step 3. Listen actively to patterns in the customer’s words, tone, and even their emotional state.
Learn how to recognize emotional words.
Step 4. Keep accurate but brief notes, differentiating situation, pain, and impact while identifying
causality.
Step 5. Empathize with your customer, consider a relevant use-case story of another customer
who experienced the same challenges, and share how they resolved it.
Step 6. Repeat what you’ve heard to ensure you understand what is being said.

A conversation connects a sales professional with the customer to uncover their real, pressing problem. It
is the moment in which a hypothesis about customer impact can be fleshed out by a trained professional.
As you can see in the next blueprint, we can apply TALKER to all kind of moments to start a conversation.

Coming out of this moment, you should have a very clear idea of whether and how your product can
impact the customer’s business. More importantly, you should have managed the conversation in a way
that the customer themselves have verbalized the problem and envisioned a potential solution.
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Figure 7.6 Example of a live chat with a customer who came to your website to learn more

Moment #3: Discovery/Demo Diagnose before prescribing your solution

As the saying goes: prescription before diagnosis is malpractice. To use a medical analogy, when a patient
is complaining of symptoms, a doctor must diagnose the issue before prescribing a course of action. In
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sales, if the salesperson were to immediately start pitching, that would be prescribing the solution before
fully knowing about the customer’s true pain.

The salesperson’s role is to further diagnose the root cause. This is still not the time for a hard sell (it never
is, by the way). Instead, the more a salesperson can do to understand the customer’s pain and the
potential business impact, the better they will be able to accurately recommend an impactful solution for
that customer.

Figure 7.7 How to have a conversation

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EXPERT ADVICE
Close-ended questions are powerful for setting context for open-ended diagnostic
questions. But too many in a row, or asking close-ended after a customer has shared a
pain or desired outcome can drop engagement that results in a mediocre conversation. A
great sales professional guides the conversation based on what their customer is looking
to accomplish, not just on the features or benefits they are comfortable talking about. This
approach will decrease sales cycles and increase the value of deals simultaneously.

DAN SMITH
Partner, Winning by Design

Questions are the only way to uncover your customers goals and objectives. To diagnose efficiently, use a
question-based framework that will work in every professional situation, from the emergency room to your
favorite car mechanic.

Step 1. First ask two or three questions to learn the context surrounding the issue
Step 2. Then ask questions to understand the pain
Step 3. Summarize: “So you have [this situation] and [that situation] causing you [this pain]?”
Step 4. Empathize “I hear this a lot,” or “You are not alone in this.”
Step 5. Identify both the emotional and rational impact
Step 6. Establish a critical event

DIAGNOSE THROUGH DEMONSTRATION

In a high velocity sale, you might find a prospect who really wants a quick demo. This does not mean that
you should jump straight into a pitch. It means that you need to integrate your diagnosis into the
demonstration: you must ensure your demo is relevant for the prospect, and give yourself an opportunity
to obtain valuable information, such as the impact your product can have on a their business.

Sales reps will often turn what should be a quick demo into a monologue that lasts 30 minutes. It shouldn’t
be a surprise that customers lose interest when this happens; there is too much information coming at
them that they cannot relate to. At the same time, you miss the opportunity to learn about their challenges
and how you could help them. Here is a visualization of customer engagement during this experience:
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Figure 7.8 H
ow to diagnose while performing a demonstration

Step 1. Write an agenda of the points you are going to demo in the context of the top priority
challenges your customer is looking to solve. Keep it to three points on a 30 minute call,
and five points on a 60 minute call
Step 2. For each demo point, summarize your previous diagnosis and point out why you are
showing a particular page, dashboard or feature of your product
Step 3. Orient the customer with the layout of your product on the screen to show them where
they should be looking to help minimize distraction or confusion.
Step 4. Then demonstrate:
● In the customer’s context, how your product solves their problem
● “Hand over” controls by asking if there is anything they would like to see
● Identify impact for each point by asking the following three questions:
“Would this address the issue you described earlier?”
“Can you see yourself using this product?”
“How would this impact your business?”
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Step 5. At the end of each, summarize the key findings, ask if there are any questions and move
to the next point
Step 6. Following the demonstration recap the findings across all three points using the customer
vernacular

Moment #4: Close Trade, not negotiate

This single change in wording has one of the greatest effects on cumulative sales. When salespeople
negotiate, they tend to think in terms of compromise, specifically with numbers and percentages moving
up and down. In a high velocity sale, we notice that they tend of offer discounts quickly and in large
increments. As a result, they often give away discounts far more than they should for little in return.

A company with an innovative SaaS product with an annual contract value (ACV) of $12,000 should
increase its price annually by at least 10% given its rapid product development. By giving a 20% discount
during negotiation, an inexperienced negotiator may view this as “only $2,400”, however this adds up over
three years to be $10,920, or nearly one year of revenue.

And for what? Most deals that reach the negotiation stage seldom turn on price. Instead, we encourage
organizations to think of negotiation as trading, and of discounts as price adjustments, and make these
price adjustments small. In trading, both parties give up something of value in order to be better off. By
definition, trading is a win-win situation. What do they trade for? There are any number of things a
customer can do or say that will significantly help a business. References, case studies, social media
mentions, PR quotes and all kinds of other items can form a menu of trading options at different levels of
price adjustment.

This puts a price on discounts, and everyone knows what happens when we pay attention to the price of
something: its value becomes clear. So, when a customer isn’t willing to do a PR mention and turns down
the discount, the average discount rate for the team goes down. This single change has caused the
average discount rate to move from more than 20% to less than 10%. That is revenue that goes straight to
the bottom line.

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Figure 7.9 How to trade throughout the customer conversation

Step 1. Know the person on the other side of the table, their way of responding, etc.
Step 2. Understand the situation: what is the impact, and the critical event?
Step 3. Prepare a list of trade items, and understand value of each
Step 4. Do you understand all the elements of the offer?
Step 5. Get all negotiation items on the table: price, terms, setup fee, etc.
Step 6. Repeat/Ask what you heard, “So if I got it right, you want ___ . Is there anything else?”
Step 7. Prioritize the issues: Let me ask, what is most important to you: Price or...
Step 8. Before you make the offer, make sure you are talking to the decision maker
“If we come to an agreement can you make the decision by {today}.”
Step 9. Make the offer, do not hesitate; be clear and be concise
Step 10. Listen and repeat the counter-offer

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Moment #5: Kick-Off Orchestration, not onboarding

Onboarding is a term that has become so overused that it’s lost its meaning. Everyone thinks they know
what it means, which usually comes down to something like “getting the customer set up with the
product.” While the technical setup may be the immediate concern, it doesn’t cover the larger missed
opportunity that this first customer interaction after commitment represents.

You must understand that the relationship before the commitment and after the commitment has
undergone a fundamental change:

● Before the contract: The buyer did not want to provide too much insight into their business for
fear of losing leverage, and perhaps the seller may not have been completely transparent on how
things really work.
● After the contract is signed: The buyer is willing to provide a lot more insight into how their
business works to ensure success. This may even involve an adjusted timeline, additional budget
available, and access to previously inaccessible executives.

This window of mutual exposure is only open for a short while. So instead of just onboarding t he customer
into the product, this should be treated as an opportunity to orchestrate the entire business relationship
from that point forward.

It is during onboarding, while the customer is vested in a successful outcome, that the seller (in this case
the CSM) has the opportunity to set expectations for how the product will impact the customer, how it is
measured in milestones of success, and ultimately set up the relationship so it has a real impact on the
customer’s business. It becomes a strategic business discussion rather than just a technical one. Just
keep in mind that you might need to treat this as two different discussions: the more strategic one which is
business focused, and the technical one which is more tactical.

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Figure 7.10 The importance of orchestrating rather than just onboarding

Step 1. Handoff the deal to the CSM/Onboarder using Impact and Critical Event details
● The sales rep should stay involved to ensure continuity
● Time is of the essence: provide short frequent communication with updates
Step 2. Redo the deal. Since the relationship has changed, the salesperson revisits all the
details with the buyer, identifies key stakeholders and orchestrates building the
relationship.
● Consider creating a 3x3: Three stakeholders on your team, each who work with
three stakeholders on their team
● Then have people from your team reach out to people on their team
● May involve sales ghostwriting the first message
Step 3. Kick-off
● Send a welcome note, a brief note, may include an icebreaker such as t-shirts
● Create the impact journey of when a specific impact is achieved
● Obtain the date when the customer has their monthly internal executive meetings
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● Establish cadence of scheduled events such as the renewal and its conditions
● Set alerts for triggered events such as opportunities and/or risks, and define the
actions you will take on each alert

Moment #6: Renew Ensure impact, not usage

Many customer success software platforms track product usage. Whether measured in percentage of
seats used, or number of logins per time period, or number of features used, product usage is often the
proxy for success. But this is measuring not customer success, but rather the product’s success.

Figure 7.11 The importance of frequent impact reports vs. a Quarterly Business Review

A more customer-centric approach would be to explore whether the customer is getting the results they
need out of the product. After all, from a customer’s standpoint, what could be better than solving their
pain with the minimum amount of usage possible?
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It’s often the case that more usage will solve the problem, in which case usage is a reasonable proxy for
impact. But be sure to keep CSMs focused on the fact that the customer is buying impact, not usage.

Step 1. Orchestrate a road to achieve desired impact
Step 2. Practice how to handle frustration when an issue occurs
● Communicate: Establish a solid way of communicating, e.g., “TALKER”
● Disarm: Express empathy/disarm the situation without taking on blame
● Research: Important to find relevant materials! Do not diagnose without it!
● Diagnose: Perform a proper diagnosis based on the research
● Proof: Before you prescribe, accumulate proof of your case
● Prescribe: Recommend based on research/diagnosis/proof
● Communicate: Summarize, and offer help to implement
Step 3. Provide a scheduled report every month that clearly indicates the impact achieve
● Report must have an easy to understand chart, visualizing the impact
● Achieved emotional and rational impact should be presented
● Present benchmark of the impact of the customer compared to others in the
industry
● Specify risks and opportunities in the impact report
● Always look forward 6-12 months regardless of the expiration date
Step 4. Renew/expand the contract well before the actual renewal due date; the renewal should
be based on the emotional and rational impact for the customer, not just the usage

EXPERT ADVICE
Treating customer success as an afterthought isn't just damaging to your company brand
- it's detrimental to your growth. We know that as much as 75% of SaaS revenue comes
after the customer commits to your product. Why risk future introductions, relationships,
branding opportunities, and revenue stream by providing a poor or non-existent customer
experience? Invest in a Customer Impact Journey early - from the sales handoff to
onboarding to realizing impact and beyond.

EMILIA D’ANZICA

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Moment #7: Upsell Grow, rather than sell more

“Land and Expand” has become a buzzword in SaaS marketing circles. It’s a useful metaphor, but it’s also
a metaphor rooted in conflict. It sees the customer as a territory to be mapped, flanked and conquered. It
is reasonable to assume that is not how the customer views the relationship. Instead, you should think
about growing the relationship and growing the customer’s business. This can only be achieved by having
an impact. Whether that impact is lower cost, higher revenue, or an improved customer experience, it is
the impact that matters to the customer - and the more impact delivered, the more the customer will want
to use (and buy!) the product.

Figure 7.12 Four growth areas, each with its own opportunity

Growth is a function of providing great impact to stakeholders inside an account. If a new stakeholder
needs to be convinced for the first time of the impact you deliver, this is referred to as a new business win,
and should be the responsibility of an acquisition-focused sales rep (AE).

When an existing customer renews the contract with no new stakeholders or impacts, it is referred to as a
renewal. Often these renewals occur automatically on or right before the anniversary of the contract. In
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many cases, the CSM is responsible for this. This is a flawed approach because you ignore the growth
potential from a customer willing to renew nine months into a contract.

When an existing customer buys more services, such as more seats or additional features, this is
considered an upsell. CSMs are capable of doing this reactively, but if you want to reach out proactively,
you are likely going to need an acquisition-focused salesforce. When a new stakeholder in an existing
account needs to be won over, this is referred to as a cross-sell. This should not be handled by a CSM, as
this the most complicated sale and you may need to unroot an existing competitor chosen by another
champion. This is often better handled by a team familiar with competitive scenarios, such as the
Acquisitions team. Each of these sale types create growth loops, each with its own specific goal.

Figure 7.13 Growth opportunities mapped back to key moments, creating Growth Loops

Step 1. Create a 2 x 2 matrix with the four growth areas.
Step 2. Assign each area to the right person in your organization. For example:
● Renewal of the contract ⇒ Customer Success Manager
● Upsell to a new product ⇒ Sales or Account Management
● Resell to a new a new benefactor ⇒ Sales or Account Management
● Cross-sell to a new benefactor ⇒ Account Management
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Step 3. Determine the growth conditions in each area. For example, under Renewal when impact
is achieved, there are still various growth opportunities:
● Annual x% increase in price
● Renew earlier, e.g., renew at 9 months into a 12-month contract
● Extend contract terms from a 12-month to a 24-month contract
Step 4. Create a blueprint for each of these growth areas, addressing the most common
scenarios.
Step 5. Practice performing these actions with the team! Do not do this with a customer without
having first practiced and role-played out the most common scenarios.

Bonus Moment: Staging of Meetings

Most business today is the result of a series of meetings. The quality of each meeting determines how
many meetings you need. We’ve found that successful salespeople have fewer and shorter meetings.

Figure 7.14 How to stage meetings to achieve the goal and shorten the sales cycle

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By reviewing tens of thousands of sales meetings, both in person and on the phone, we’ve found that
great meetings follow a consistent blueprint:

Step 1. ACE the meeting. Check the end time and set the end goal of the meeting:
● Appreciate: Appreciate you taking the time to meet today.
● Check time: Are we still good until 11am?
● End goal: The End Goal of this introductory call to see if we can help you. If so,
we normally move forward with a demonstration. Does that sound good?
Step 2. Present an agenda to meet the end goal and ask the customers to contribute:
● What else would you like to discuss today?
Step 3. At the end of the meeting, ask if the goals were met:
● May I ask, based on what we discussed today, do you think we can help you?
Step 4. Confirm that the client is ready to move forward:
● Are you ready to move forward with a demonstration?

Next is a critical part where we link to the outcome of the next meeting.

Step 5. Set the stage for the next meeting:
● Have you done a demonstration like this before?
● What has been the outcome of a successful demo in the past?
Step 6. There are three ways to get the right people in the room to achieve the end goal.
Ask with an open-ended question:
● Is there anyone else who can benefit from attending this demonstration?
Ask with a closed-ended question:
● Mary is your head of Sales Ops, right? Do you think she can benefit from attending
the demonstration?
Ask with a third party reference:
● I recently did a demo with {{first name}}, she is one of your peers and decided to
bring in her head of Sales Ops to address the integration with your CRM. I notice
Mary is your head of Sales Ops. Do you think she can benefit from joining us?
Regardless of the outcome, you can always follow through:
● Since Mary can’t join us, what does she normally care about?

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RECAP Blueprints

To impact change, we recommend the following steps:

Step 1. Identify the key moments for your business
Step 2. Measure the conversion metrics and maintain a trendline over time
Step 3. Determine the actions performed during the key moments, and visualize them in a blueprint
Step 4. Brainstorm how each key moment can be improved
Step 5. Iterate in 15- to 30-day intervals until you have improved each metric by 10%
Step 6. Benchmark your performance against others relevant to your business

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CHAPTER 8
DATA-DRIVEN
ORGANIZATION

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With so many tools and ways to capture data, it’s very easy to get overwhelmed with this data explosion
and become lost when trying to boil it down into meaningful insights. It results in either no action, or taking
the incorrect action that could have an adverse impact. Since most decisions in sales today are guided by
data, we have to establish the data model. Let’s start by standardizing what we are going to measure.

Figure 8.1 End-to-end sales methodology with customer-centric measurement points

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Key SaaS Metrics and Definitions

There are three types of metrics that contribute to the standard data model:

1. VOLUME METRICS: Tracks the volume of leads, opportunities, deals and revenue

SUSPECT A person who may be interested
PROSPECT A person who fits the profile
MQL [Marketing Qualified Lead] A person who expresses interest by visiting your website, for example
SQL [Sales Qualified Lead] A person who has a pain and wants to take action to impact the situation
SAL [Sales Accepted Lead] Verified by a sales pro that an impact can be achieved within allotted time
COMMIT Mutual commitment to deploy a solution that will impact the problem
LIVE Customer has been onboarded: on time, within budget and the solution can deliver impact
MRR Solution delivers impact again and again and a recurring revenue stream is secured
LTV The revenue an account generates over its lifetime, net of churn and including growth

2. CONVERSION METRICS: Shows how effectively you are progressing leads and opportunities through
the sales cycle (e.g., what is the lead-to-opportunity conversion rate, win rate, churn rate)
CR1 PRO → MQL Prospect to MQL rate, indicative of the quality of the database
CR2 MQL → SQL MQL to SQL rate, indicative of the quality of lead development campaigns
CR3 SQL → SAL Showrate, hand-off, indicative of the quality of the prospecting work
CR4 WR Win rate, indicative of the quality of the total sales process and the sales skills
CR5 Onboard Churn Churn during onboarding, indicative of quality of the client experience
CR6 Usage Churn Indicative of the stickiness of the service; lack of impact results in churn
CR7 Growth Upsell during usage during the length of the contract

3. TIME METRICS: Shows how long it takes to move leads and opportunities through the stages of the
sales cycle (e.g., time to first use, time to first value)
ΔT1 Duration of prospecting before engagement is achieved, measured in days
ΔT2 Duration of the prospecting campaign, indicates the quality of sequences used
ΔT3 Time it takes to set up meetings and convert them into qualified opportunities (ideally <5 days)
ΔT4 Sales cycle indicates the ability of a sales manager to navigate through the client’s process
ΔT5 Time to live indicates the complexity of a product, anywhere from seconds to weeks
ΔT6 Time until a client has achieved the desired impact, often a 12-month contract
ΔT7 Time to achieve penetration of an account
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CRITERIA PROSPECT MQL SQL SAL WIN LIVE ARR LTV
Is a fit Yes Yes Yes Yes Yes Yes Yes Yes
Engages with selected content Yes Yes Yes Yes Yes Yes Yes
Meets with an expert to discuss impact Yes Yes Yes Yes Yes Yes
Impact identified and we can solve it Yes Yes Yes Yes Yes
Executed mutual commitment Yes Yes Yes Yes
First impact achieved? Yes Yes Yes
Recurring impact achieved? Yes Yes
Total lifetime impact achieved? Yes

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Creating Actionable Reporting Structure and Dashboards

What metrics should be reported to each of your stakeholder audiences when you have a sales team in
place with roles across the sales cycle? Use this as a guideline.

Table 8.1 Metrics that should be reported for each of your stakeholder types
EXECUTIVE/BOARD SALES MANAGERS SALES REPS
Monthly Growth/Speed: Performance Metrics: Performance Metrics:

(Board) (1) Pipeline created: SQLs per week MQLs/Campaign MQLs/Campaign
SQLs/SDR SQLs/SDR
(2) Pipeline developed:
MRR/AE MRR/AE
Win rate + ACV + Length of the
Deals/AE, Deals/SDR Deals/AE, Deals/SDR
Sales Cycle
Sales Cycle/AE Sales Cycle/AE
(3) Pipeline closed: MRR growth MoM + Win rate/AE Win rate/AE
number of deals
Ramp:
(4) Customer churn (logos and revenue)
Time it takes from
SaaS Metrics: onboarding new rep to hitting
(1) Customer Acquisition Cost 80% of quota (<90 days for
(2) Lifetime Value/LTV application, <180 days for
(3) Average contract length (months) platform)
(4) Payback on CAC (months)
(5) Quota performance team
Weekly Leading Indicators: MQLs/Campaign

(Execs) - #MQLs, #SQLs SQLs/Rep
Trailing indicators: SQLs
- Deals, MRR MRR/Rep
Meetings/Demos
Daily N/A Deals Email metrics

Phone call metrics

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EXPERT ADVICE Would you drive a car differently if we took away your speedometer
and gave you only a fuel-efficiency meter? Research on the Toyota Prius suggests this is
the case. In other words, the data displayed on the dashboard changes behavior.
Remember this as you build your dashboard!
JACCO VANDERKOOIJ
Reporting to your Board

Reporting to your board may always have some level of stress associated with it, but don’t let that stress
come from creating dashboards and charts in the last hours before the board meeting. In the chart above,
you will not have the data for all of those metrics right when you start out. So here are the metrics that you
should be focusing on, by stage.

Table 8.2 Key metrics that you should be tracking and reporting on by stage (cumulative)
General Revenue Revenue + Bookings Revenue + Bookings + Cash

Deals won Forecast 30/60 days Forecast 90/180 days
Pipeline of deals Inbound vs outbound leads Leads per campaign
Inbound leads Pipeline by stage Pipeline generated/campaign
Website visitors Sales cycle (win/loss) in days Prospect ⇒ MQL (CR1)
Content/Event metrics SQL → Win (CR3xCR4) SQL → SAL (CR3)
MQL → SQL (CR2) SAL → Win (CR4)
Customer churn (logo, revenue)
Growth from new logos
Leadership Average deal size Activities per Rep

Time to get to 80% of sales Deals per Rep
cycle Bookings per Rep

Execs/Board Focus: Key wins and Focus: Sales effectiveness Focus: Sales efficiency and
Product-Market Fit and Go To Market Fit growth metrics, such as
Lost opportunities to metrics such as CAC, ACV, YoY/QoQ performance and
understand why and Conversion Rates # of reps reaching targets

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Figure 8.2 Example set of metrics for board and executive level reporting

Below is an example of the level of detail that you can easily create in Excel or Google Sheets on each of
those metrics listed above:

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Figure 8.3 Example of how to report growth in new logos

Commons Questions

Q: What comes first: SQL or SAL?
A: In SaaS sales, first you qualify, then you accept. To clarify, think of a visit to the emergency room as an
example.

Figure 8.4 Example of a visit to the emergency room

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Q: We have lots of SQLs, but my sales team is not closing. Who is at fault?
A: Look at the relationship between CR3 and CR4. Remember that CR3 is the conversion rate from
SQL to SAL (shows the quality of the leads that the SDR has developed), and CR4 is the conversion rate
from SAL to win (shows how effective the AE is at closing opportunities).

There are a variety of reasons why opportunities are not closing:
● No-shows: Prospects who commit to a meeting, but don’t show
● Unqualified: Prospects who, upon further review, can’t be helped by us (at this time)

Table 8.3 Insights from a comparison of CR3 and CR4 win rates
CR3
CR4 < 80% ~ 90% > 95%
< 15% Process issue: Cold calling with AE accepts too many leads; train Train SDR to qualify with more
no relevance; train SDR on on how to diagnose rigor, and train AE to diagnose
identifying leads who have a pain on priority
~ 20% Train SDR on identifying leads Effective and efficient team; Add an AE to the POD
who have a pain record and replicate the process Too many leads
> 25% AE is only taking on deals that Add another AE to your team Add another sales POD
are ready to close

Q: What is a healthy growth rate?
A: A healthy growth rate is:

EXPERT ADVICE If you think about growth from years one through three (from the
moment you start to monetize)...

Year 1 Year 2 Year 3
Good growth rate: $500K ARR → $1.2M ARR → $2.5M ARR
Great growth rate: $500K ARR → $1.5M ARR → $3.5M ARR
Top growth rate: $500K ARR → $2.0M ARR → $5.0M ARR
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RYAN CAHILL

Q: I am not achieving the “triple triple double double” (3x 3x 2x 2x growth quarter over quarter).
What is wrong with me?
A: Nothing is wrong with you. Starting a company takes a lot longer than you think.

Q: What is more important; Growth or profit?
A: This is rapidly shifting. In 2015, it was growth at all costs. However, it’s now shifting to
profitability. Investors no longer want to fund an unprofitable business. Up to $1M in ARR, you are still okay
to tinker with your go-to-market model, but after that, you cannot spend more than 40% of the annual
cost of marketing and sales in order to acquire new customers and revenue. In other words, the cost of
marketing and sales cannot exceed 40% of your revenue.

Q: Is monthly churn different from annual churn?
A: Very different! With annual contracts (often for platform sales), customers churn at a much lower rate.
A common churn for annual contracts is 5-8% (annually). For monthly contracts, between 1-2% (monthly).

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Common Pitfalls

Pitfall 1: Misunderstanding platform vs. application business. Benchmarks for KPIs of application
sales compared to platform sales can be very different. Be sure that you are benchmarking your data
against the right ones that apply to your business.
Pitfall 2: Leaving board reporting to the last minute. Set up your format and agree with your
executive team on what to report on and how. Set up an Excel or Google Sheets workbook well ahead of
time, and set up a system so that your charts will automatically update with new data. Spend your prep
time before boarding meetings thinking about the “why” behind the numbers, rather than stressing over
data errors and chart formatting.

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Sales Compensation
Now that we know what metrics to watch, we can apply this to creating a sales compensation plan for the
team. See here for an example of how this works for a POD with one SDR, 2 AEs and 1 CSM.

Figure 8.5 Calculating compensation for a POD

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Here is how this translates into a compensation plan, this example for an SDR:
Table 8.4 Example structure of sales compensation for an SDR
Title Sales Development Rep Seniority Jr SDR [ ], SDR [ X ], Sr. SDR [ ]
Reports to Sr. Dir of Partnerships Quota Generate 20 SQLs per month
On Target Earning $ 60,000 Compensation Mix 75%, 25%
Base Salary $ 45,000 Sales Incentive $ 15,000

PLAN PER SQL <= ACV<50K PER HV SQL > IF SQL ⇒ PAID
COMPONENTS ACV>$50K CONTRACT
Rate/Amount $ 25 per SQL $50 per SQL $100 per Contract Quarterly
Cap No Cap

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CHAPTER 9
CULTURE

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Why does culture matter?

The sales culture you create is going to be one of the key components that determines if your company
thrives, survives or dies. Every company will generate their unique sales culture that reflects their
customers, founders and the company - but the high performing sales teams share a few common pillars
of their culture that lead to success.

EXPERT ADVICE Create a winning company strategy from Day One. That means
putting customer centricity and team success at the center of your culture by clearly
defining company-wide goals, a vision, and values that everyone is accountable for
upholding. Being part of a bigger purpose will not only motivate employees to strive
for excellence, but will also align the company with shared beliefs. This cultural
accountability will prove its value during the most challenging quarters - when
everyone roles up their sleeves and works together to meet or exceed goals.
EMILIA D’ANZICA

Key pillars of culture
There are four key pillars that you should adopt to realize a successful culture for your team:
1. A clearly articulated company mission and revenue goals
2. Science-based methods
3. Strong organizational trust at all levels
4. Objective coaching delivered to the team

Clearly articulate your company mission and revenue goals

Having a clear understanding of your organization’s ‘why’ is a key building block of your unique sales
culture. This will enable you to hire the right candidates, shape your customer engagements and manage
performance in a manner that aligns to your company values. For a quick and powerful primer on what it
means to find the ‘why’, hear it directly from Simon Sinek in his TED Talk called “How Great Leaders
Inspire Action”.
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Be deliberate. Write down your ‘why’ and clearly communicate it to your sales team and to the candidates
that you are recruiting. Once you have the ‘why,’ you must articulate sales goals and objectives that clearly
align to your ‘why’ and the high-performing sales team will tie their goals to their efforts on a daily level.
Why daily? Sales is a tough role that requires significant persistence in the face of rejection, so aligning
your daily sales effort to the broader organizational objectives is key to creating a culture of learning and
success.

Adopt science-based methods for making decisions

Let’s first talk about what is often the antithesis of a science-based culture. That would be a “superstar
culture.” A superstar sales culture is one that relies on high-achieving individual contributors to win big
deals. These superstars use enterprise-level sales skills developed and tuned over long years of
experience.

A science-based culture means getting scientific and specific with the numbers. This means identifying
your target sales goal for the team, and then reverse engineering that process to identify the leading
metrics that will lead to hitting that target. Keep in mind that in some instances, you will have new roles
and won’t have a clear path of what the ‘math for success’ is. Using industry best practices, create a
benchmark to work toward, and then refine from there. See below for an example of how this is done:

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Table 9.1 Assigning goals to each key metric in order to line up with the overall team goal
SDR Daily Inside Sales Weekly Enterprise Sales Monthly
Prospect into cadences 50 Diagnose calls 10 Account plans 20
Conversion rate 6% Conversion rate 50% Conversion rate 40%
Conversations 3 Demonstrations 5 Opportunities 8

Conversion rate 33% Win rate 40% Conversion rate 50%
SQLs booked 1 Won deals 2 Proposals 4

Conversion rate 0% Win rate 25%
Won deals 1
ACV $5,000 ACV $150,000

Monthly 20 Monthly $43,333 Monthly $75,000
Annual 240 Annual $520,000 Annual $900,000

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Build organizational trust at all levels

A strong sales culture isn’t built by a single individual, manager or founder. It requires commitment across
the entire team to continuous learning and using agile approaches to scale. Some keys to building
organizational trust:

● Building shared accountability: Encouraging individuals and teams to hold themselves
accountable for their own actions. You will find that this becomes much more natural for teams if
they see their leaders doing this themselves.
● Displaying high emotional intelligence: Although we are engaging in a business environment,
we are still human and need to take that into account with all interactions within the business.
Everyone deals with challenges and opportunities differently. Take the time to understand your
team and support their own approaches.
● Supporting individual growth and success: We need both the organization and the individuals
to be on a journey of continuous improvement. For the team, this means creating shared learning
opportunities. For the individual, this means spending one-on-one time to understand their
personal motivations, what they want to get out of their roles, and what skills they need to progress
their careers.

Deliver objective coaching to the team on an ongoing basis

Sales managers and leaders often talk about themselves as sales experts who manage their teams. They
are making the mistake of leaning too much on the word manager. Managing people is actually an
outdated approach to leadership. Instead, we need to coach our team members: This means creating a
collaborative learning environment that continually evolves and learns through coaching. How do you put
this into practice? We recommend following the 70-20-10 principle.
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Table 9.2 The 70-20-10 principle for managing coaching time
70 - 20 - 10 PRINCIPLE
10% - Regularly educate your team on your target customer and blueprints
Teaching that enable them to have better conversations
- Rely heavily on visualization of your processes and principles to drive
engagement and conversation
- Task your team members with teaching; you want to encourage people
to see it, do it and teach it
20% - Use our coaching guidance: coaching should be objective rather than
Coaching subjective, based on the execution of the sales process
and - Coaching is not only on the shoulders of managers: everyone on the
learning team should be empowered and educated on how to provide objective
from peers coaching feedback. This coaching needs to happen throughout the
week, and should be a mix of formal and informal.
70% - Reps will learn their skills and weaknesses when applying the learned
Application skills in live and simulated environments
- Learning and selling needs to happen concurrently and the best way to
avoid the forgetting curve is through repetition

Performance Management

Here are some best practices for performance management and conducting reviews:

● Weekly 1:1 pipeline reviews with a set weekly format for reading out accounts (see the Annex for
the template)
● Try to help solve roadblocks, rather than just talking through the details of an account
● Keep in mind that the most common mistakes that reps make are:
○ The AE wants to do it himself rather than ask for help from his manager
○ There is only one contact/relationship with the account
○ Not doing the basic blocking and tackling according to the sales process
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● Common mistakes that sales managers make when conducting pipeline and performance:
○ Not providing coaching on how to change their behavior, not just what to change
○ Most problems here are related to process, not to people. Make sure that you have the
right processes in place for your reps to follow for good pipeline hygiene. For example:
What are the top five critical events you sell against? What impact are you creating for your
customers? What are the use cases for different customers?
○ Keeping coaching to themselves: Coaching should be owned by the team; senior reps
should be coaching junior ones. Reps who have done a certain type of deal before should
be coaching other reps on those deals. Managers should have the entire team take
ownership of coaching and of elevating each other’s skills.
● Group call review: Teams should review a minimum of two calls each week at the end of the week

Commons Questions

Q: Shouldn’t my sales managers manage the entire process, and not just the moments that
matter?
A: We hear you, but it’s these key moments that make the difference. Sales managers won’t have
the bandwidth to micromanage the sales process for all of their reps - nor should they. They should only
need to focus on these Moments that Matter, and that will make the difference.

Q: Should I have my AE do prospecting?
A: Depends on your ACV! In platform sales, the AE should do his own prospecting rather than an SDR
prospecting and and then handing leads to the AE. In contrast, for high-velocity application sales (below
~$15K ACV), you should likely be using a multi-role sales org (SDR prospecting and setting up meetings
for the AE).

148

Table 9.3 Who should do the prospecting based on your ACV
ACV STAGE 1 STAGE 2
< $1K Marketing develops the leads Online order form
< $10K (application) Marketing develops the leads Jr. AE closes
$10K - 40K SDR develops the leads AE closes
$40K + (platform) AE develops the leads Sr. AE closes

Common Pitfalls

Pitfall 1: Improper handoffs. It’s crucial to ensure that your different sales roles execute smooth
handoffs (e.g., from AE to CSM/ONB as a customer is onboarding). These are important moments to the
customer, and they must know that everyone at your organization is coordinated in working to help them.

Pitfall 2: Reaching out to prospects who are a fit based on key demographics (e.g., title,
location, etc.). This will send your company into overdrive, but it’s very ineffective. Doing so means you’re
targeting using inefficient ‘fit’ characteristics, but not identifying the customers who actually have a ‘pain’.

Pitfall 3: Treating the kickoff call for new customers simply as a time to get them onboarded
with your product. When a lead has committed to you and become a paying customer, the kickoff call
becomes a very important moment. This is the point at which your relationship with that customer has
changed: you now have the shared goal of making them successful. Now is when you are setting the tone
for your ongoing relationship with them.

149

How to structure coaching conversations

STEP 1 Identify the types of meetings you need to conduct, and how often
(d) daily, (w) weekly, (m) monthly, (q) quarterly

INDIVIDUAL (1:1) TEAM MANAGING UP
Business plan review (m) Standup routine (d) Executive roll-up (m/q)
Personal development review (m) Pipeline update (w)
Pipeline review (w) Learning dojo (w)
Sales coaching (w) Business review (q)

STEP 2 Set the duration and timing for your meetings
Use the following table to help your team understand the expectations for each type of session.

150

Table 9.4 The types of coaching meetings, and how they should be used
MEETING DURATION / DESCRIPTION

FREQUENCY
Business plan 60-90 mins The rep should review his performance from the previous month,
review monthly outlining the goals for the following month and plan to execute.
Manager should challenge the rep, clear obstacles and coach towards
a positive result.
Personal 30 mins Manager works with the rep to define personal and career goals, and
Development monthly map against the rep’s current skill set. Rep should review what he has
accomplished in personal development, and set goals for the coming
month.
Pipeline review 30 mins Reps present their pipeline to the team, focusing on challenges.
weekly Managers should ask for details, understand why deals may have
slipped, help to clear blockers, and identify possible missed
opportunities to drive more customer value.
Sales coaching 30 mins weekly Discuss areas of opportunity and improvement that manager can
determine from sitting in on live meetings, calls and onsite visits.
Standup routine 15-30 mins A daily huddle between the team to review yesterday's performance,
daily set intentions for the day and warm up with ‘ring-ring’ exercises.
Pipeline update 45 mins Review leaderboards from last week, review pipeline to close this
weekly week, and declare individual goals.
Learning dojo 60 mins A weekly session with a focus on increasing rep effectiveness. Focus
weekly areas should be identified by the team, guided by data. Sessions are
to be run by individual reps and supervised/supported by the manager.
Business review 60-90 mins The start of the quarter is an opportunity to align the team to business
quarterly goals and inspire continuous improvement; review metrics with reps
highlighting top five current and next period opportunities.
Executive 30 mins Review current and next period forecast. Discuss target for current
roll-up weekly month and potential gap review, upsides and next steps.
151

STEP 3 Schedule your cadence for the week
This might seem obvious, but don’t schedule meetings during ideal selling time: Take into account when
your customers are available for meetings, and when your team will be most productive. Every sales team
will settle on their own slightly different cadence, but here is an example to get you started.

Figure 9.1 A sample cadence of weekly recurring meetings

152

STEP 4 Map out your quarterly plan

Apply the same guidelines to your quarterly plan by mapping out a cadence of your monthly and quarterly
meetings.

Figure 9.2 A sample cadence across each week of individual, team and executive meetings

153

STEP 5 Create a sales coaching calendar

Table 9.5 A sample coaching calendar
FREQUENCY OBJECTIVE TRAINING TOPIC EXAMPLE THEME
Quarterly Review overall sales results and Review the need for any “Improve our win rates”
adjust your strategy. Set effort, formal training on value
knowledge and skills targets proposition, customer
campaigns or competition
Monthly Set a specific improvement Review the results of your Month 1: Discovery to demo
objective for each month related sales plays and make conversion
to the quarterly objective minor tweaks to Month 2: Demo to proposal
sequences and plays Month 3: Proposal to win
Weekly Review efforts and fine tune “Flight School” Focus on a different aspect of a
skills Hands-on review of particular skill for narrow focus
critical sales activities, (e.g., call review)
such as account plans, Week 1: Opening a call
proposals, recordings of Week 2: Asking questions
discovery calls and demos Week 3: Summarizing pains
Daily Practice through role-playing 15 minutes of role-play Day 1: Situational questions

with each other daily Day 2: Pain questions
Day 3: Impact questions
Day 4: Critical event questions

STEP 6 Communicate with your team
Key to ensuring success is to set the vision for what your team will be able to accomplish as a result of this
schedule and rigor. Framing coaching as a collection of meetings doesn’t sound interesting or valuable.
Rather, explaining how these sessions will help the team up-level their skills, give them a better chance at
meeting their goals and help the team be a highly tuned machine will motivate them to get involved and
participate.

154

Hiring your Sales Leader

Though culture comes from the entire team, it’s your sales leader who will certainly set the tone. Be sure to
watch the video by Simon Sinek called “Why Leaders Eat Last”. It provides a great outline for a modern
sales leadership culture, and Simon shows how it is based on four chemicals.

Figure 9.3 The four brain chemicals that drive behavior

155

Table 9.6 A new kind of leadership
ENDORPHINE DOPAMINE SEROTONIN OXYTOCIN
Makes you feel good so Positive feeling, drive. Feeling of pride & status. Feeling of love and trust,
you can perform work. Makes you feel happy We seek recognition. Gives the warm and fuzzy feeling
“Runner’s high” masks when you achieve confidence, and reinforces that someone has your
physical pain. Gives us something. social structure and back. Act of generosity
consistent endurance. compassion for others. based on time and effort.
Makes you work hard. Makes you goal driven. Awards. Pride. Sense of Sacrifice time and energy
allegiance, organization to help team members.
cohesion.
Have people perform and Motivate people to Talk to them to share your Let team members feel
work at their own pace. achieve goals. Help them thoughts instead of via they make a difference. Sit
Help them perform as a go after it. Check things email. Be accountable for down next to them and
team. Let them practice off a “to do list.” mistakes made. Lead by offer assistance. Make a
with each other. Help Demonstrate progress to example. “Show up.” call for them. Incentivize
them coach each other. elevate team Contagious: Spreads coaching with
performance: Combined from one person to experiences. Infectious,
with $, this is addictive. another. (likely to spread).
A more selfish, historic approach: A selfless, modern approach:

Focuses on training Focuses on coaching
Do the Work, Work hard, Achieve the goal, Get Paid Lead by Example, Give Time, Sacrifice, Share

So when you are looking to hire a sales leader, be sure that you are looking for the candidate who has that
selfless, modern approach - someone who will be a coach for your team, and not just someone who
works hard. Here are a few more specific ways that this would manifest in behavior of a leader:
● Motivating the team to work hard
● Helping them achieve goals through shared work
● Leading by example (not a desk jockey or a spreadsheet manager)
● Actively developing and sharing best practices, and encouraging others to share
● Helping team members elevate their skills by coaching rather than just fixing
156

● Getting the team to operate in a way that is greater than the sum of the individuals

There’s so much more that goes into hiring your VP of Sales, and some organizations end up taking more
than a year to find the right person. Be sure to work with your board and advisors to agree on the specific
qualities and skills that your team needs; this will make the search process much faster and more effective.

Common Questions

Q: Why can’t I just hire a few superstar sales reps and let things ride? Won’t a great culture just
naturally happen if you get high performing people?
A: Yes - it will get you to $1-2M, but what gets you there will stand in your way to achieve the next level.
You must plan for scale, and superstars don’t scale.

Q: Should I set the corporate culture, or let the team set it?
A: Many leaders believe they should set the culture as a reflection of themselves. This can be very
hard on the people for the company. They will not work as hard as you do, they are not going to be as
motivated, and they are not as stressed. You should put your personal stamp on the culture if you like, but
the majority should come from the team.

Q: Should I tweet my opinions about things not related to the company such as politics?
A: This is a hot topic among sales leaders. There are two opposing points of view, both of which are
valid:
● You represent all people in your company - both the red and blue team. As such, you should never
pick a side. This is the more politically correct (and common) leadership model. Here, we
recommend that you focus 100% on the company with a few personality tweets.
● Your people look to you to represent them. As such, they want you to voice their opinion in a
balanced and composed way. Here, we recommend that you stick to signaling a few core
principles that directly relate to what is going on in your world.

This is a highly sensitive topic, and we suggest that you discuss it with your executive team. This topic can
have positive or negative ramifications on hiring, tone, culture, etc. Do not just go out and voice your
emotions.
157

Common Pitfalls

Pitfall 1: Relying on a superstar sales culture. There is often a misconception that having “superstars”
on the sales team is what contributes to a winning culture. Interestingly, the overwhelming majority of sales
teams out there rely on superstars to deliver 80% of their results. It’s easy to think that the best way to
grow and scale is to hire as many superstars as you can. What could be wrong with that, right? Nothing to
get you to the first $1M or even $2M in ARR. But companies with this type of sales culture will inevitably be
dependent on a single performer: at first, it’s the Founder CEO, who trains only sporadically (if at all), and
will incorporate little discipline and methodology into their operations. When this type of organization tries
to scale, the entire system breaks down, because there is nothing to scale. Instead, successful
high-growth companies should make the transition to a process culture, followed by using technology to
act as a force multiplier, and then enablement, skills, and finally the team.

Figure 9.4 The Superstar culture may get you to $5M, but you need a Science culture to scale beyond $5M
158

Pitfall 2: Alpha sales leader in a team culture. The alpha sales leader is going to focus more on the
individual rather than the team. They will certainly follow the general concept of ‘work hard, hit goal, get
paid’ but you actually need someone who focuses on collaboration, helping each other, and shared
success. That’s the sauce that leads to a sustainable sales culture where team members feel supported
and will want to stay.

Pitfall 3: Coffee machine startup culture. Lots of startups are making their office spaces look and feel
like a high-end hipster coffee house, and that will attract employees who place importance on that
environment (and therefore spending 1.5 hours sipping a latte each day). Obviously, you want your office
space to be welcoming - but make sure that your space doesn’t go overboard. The appearance of the
space can easily start to manifest in your team culture.

Pitfall 4: No deep work space. The open floor space, while it’s all the rage these days, doesn’t allow for
‘deep work’. People interrupt each other, the coffee machine is brewing, the TV is showing news, people
are talking! Super cool, but no deep work happens - such as focusing on researching a key account,
writing a proposal, calculating a price, and so on. Think about dedicating a ‘library room’ where employees
can go for undisturbed deep work (think of the ‘no talking’ area in a public library, or the train’s ‘quiet car’).

Pitfall 5: Urgent vs. Important. Early stage companies often struggle to recognize the difference. We
recommend that as an executive team, you spend time discussing this to determine at a high level which
is which.

159

Table 9.7 How to think about and prioritize what is urgent versus what is important
URGENT NOT URGENT

MANAGE FOCUS
QUADRANT OF NECESSITY QUADRANT OF QUALITY
These are the daily tasks that are high These are the daily tasks that, if you do not
I priority, needing a sense of urgency - write them down, you will forget about. And
M and completely necessary for forgetting about them will cost you 2x more
P performance in your role: time the next day:
O
R ● Return phone calls ● Planning your day/week
T ● Calendar meetings/send invites ● Studying your use cases
A ● Check LinkedIn visits ● Playing with your own product
N ● Discovery calls prior to demo ● Account prep/updating CRM
T ● Deadline-driven projects ● Quiet time/break time
● Schedule internal meetings ● Responding to flagged emails
● Focusing on key accounts

● SDR/AE conversations

MITIGATE AVOID
N QUADRANT OF DISTRACTION QUADRANT OF WASTE
O While you may feel these activities need Many of the activities in this quadrant are
T your attention right away, this is where well-known to eat up your time. Know that
you get distracted and spend too much engaging in too many of these activities is
I Temper these activities by setting strict what causes stress in your life every day:
M time limits per day:
P ● Texting
O ● Chatting (Slack, GChat etc.) ● Surfing, online shopping
R ● Social media updating ● Excessive breaks/long lunches
T ● Checking and answering emails ● Selecting your music list
A ● Most 60-minute meetings ● Chatting 15 mins with 20 people every
N ● Writing reports day
T
160

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WHY YOU SHOULD READ THIS BOOK

CHAPTER 2 ORGANIZATION 22

CHAPTER 3 THE SALES PROCESS 44

CHAPTER 4 TECHNOLOGY STACK 58

CHAPTER 5 PROFESSIONAL SKILLS 74

CHAPTER 6 SALES ENABLEMENT 90

CHAPTER 7 THE SAAS METHODOLOGY 102

CHAPTER 8 DATA-DRIVEN ORGANIZATION 126

CHAPTER 9 CULTURE 140

Stephen Millard, Chief Platform Officer and Partner, Notion.

THREE KEY PHASES OF SCALING A BUSINESS

INFRASTRUCTURE AND BUILDING BLOCKS FOR SCALING YOUR GROWTH

Culture A customer-centric culture: not hard-driving selling, but rather assisting

KEY BUILDING BLOCKS

Figure 1.1​ The Elements of a Scalable Design

The term “growth hacking” is being tossed around

Key #1 Key #2 Key #3

KEY #1. FIND PRODUCT-MARKET FIT

KEY #2. HIT THE LAUNCH WINDOW

Culture Founder Founder CEO

Methodology Founder VP/Dir. Sales CRO/VP

Data Founder VP Finance/Dir. Sales Data Analyst

Organization Founder Founder/VP/Dir. Sales VP Sales+VP HR

Enablement Founder Dir. Sales + VP Marketing Sales Enablement

Skills Founder VP/Dir. Sales VP Sales

Technology Founder VP/Dir. Sales Sales Operations

Process Founder VP/Dir. Sales VP/Sales Ops

Table 2.1​ Framework for identifying a strong early hire

HITS QUOTA? ESTABLISHES COACHES OTHERS?

Usually, but will let you

Great Establishes and improves Proactively coaches

Q. ​How do I compensate this new sales person?

DISCOUNT/GIVE ASK IN RESPONSE

5% Introduction to two prospective customers

Short use case video, tweet, or G2 Crowd

15% 2-year contract, paid annually upfront, speak at an event

20% 2-year contract, paid upfront, host a workshop

Phase 3: Scale Up

SALES ROLE QUICK REFERENCE FULL DESCRIPTION

Helps to resolve Manages relationships with customer, provides admin support

Manages customer accounts, ensures that customers are

Handles the onboarding process for brand new customers to

Figure 2.5 ​The organization now starts to

Organize the team in a POD

Why do PODs work well, and why should you use

Table 2.4​ POD Modeling

EFFICIENCY SPECIALIST POD Base+Variable=OTE METRICS DESCRIPTION

MDR 500 MQLs

SDR 1 $50K+$30K=$80K 15 SQLs (O) per month

Jr.AE 1 $80K+$30K=$110K 20% WR Wins three deals per month

TOTAL 5 $415K $1.162M ARR generated / yr

STANDARD INBOUND OUTBOUND TARGET

Methodology Transactional Solution Consultative Provocative

Prospecting Inbound Outbound Target Identify

Hand-off CRM CRM + Email 1:1 Meeting 1:1 Meeting

Trade Buy Trade Negotiate

Go Dark Nurture Outbound Alerts Provoke

Onboard Enable Install Integrate Onboard

Figure 1.1 The Elements of a Scalable Design

Table 2.1 Framework for identifying a strong early hire

Q. How do I compensate this new sales person?

Figure 2.5 The organization now starts to

Table 2.4 POD Modeling

Table 3.2 A snapshot of a generic SaaS Sales process

Hello <First Name>,

Customer Relationship Google Sheets(G)/ Hubspot Free(S)/ Salesforce/

Outreach/Prospecting MixMax(G) MixMax(G) MixMax(G)

Table 5.3 Recruiting strategies, by phase

Communication (Moment 1) x x x x x

Prospecting (Moment 2) x x x

Conducting discovery (Moment 3) x x x x x

Diagnosing the issue (Moment 3) x x x

Trade (Moment 4) x x

Onboard/Orchestrate (Moment 5) x

Use/Achieve Impact (Moment 6) x

Dear <First Name>,

Dear {{ First Name }},

Moment #5: Kick-Off Orchestration, not onboarding

Moment #7: Upsell Grow, rather than sell more