The Unrivaled Guide to Onboarding

Emails

You’re getting a lot of website visitors, and your visitor to trial conversion rate is north of 10%.
Yet, it’s too early to pop that champagne bottle you’ve kept in your cupboard since your
prom.

To your avail, the majority of your trials are not returning to your site!

To prevent user drop-off at this sensitive stage in your funnel, you must nail down your
onboarding emails.

Well, this guide is all about onboarding emails and helping you increase your trial to paid
user conversion through emails.

I’ve spent a lot of time researching onboarding guides, books, reports, and email sequences,
so I can bring you the most essential and practical information on creating effective
onboarding emails.

As aways strategy beat growth-hacks. Apart from providing you with a list of example
onboarding sequences, I’m going to dish out plenty of concepts and frameworks so that if
you decide not to use a carbon copy of these email templates, you'll still walk away feeling
like you learned something about onboarding.

Who is this guide for?

This guide is for SaaS (Software as a Service) companies with a free trial or a freemium
model that want to convert more users into paying customers.

People with products and services that want to nurture leads into customers are also going
to find practical application.

So, without further ado, let's get it on and convert some of those trials into paying customers!

If you’re looking for inspiration of onboarding email sequences skip to here.

1
Get Started With Onboarding Emails

Onboarding emails are just an output you create as a marketer; a small building block, part
of the complete marketing system you created to guide people towards success with your
product.

In isolation, onboarding emails won’t make your startup successful. But as a part of a well-
designed funnel, they can certainly help.

Before you dive in user onboarding strategies and tactics, I encourage you to answer these 3
questions:

1. Do you need to focus on user onboarding now?

2. What’s the quantitative goal of your onboarding campaign?

3. What’s the desired outcome of your onboarding emails?

1. Do You Need to Focus on User Onboarding Now?

I know, a bit contradictory considering this post is all about onboarding, but I really don’t want
you to invest your time on the wrong things.

As I showed in the marketing automation strategy guide onboarding happens in one stage of
your funnel – it doesn’t really matter what the name of that stage is, but usually, it is towards
the beginning of your funnel.

2
 

Being a ridiculously busy founder or marketer, you only have the resources to focus on a
single stage at a time. Bigger and well-funded startups have people in charge of email
marketing and whatnot, but I’d assume that you don’t have a full-time owner of onboarding
emails, so my advice is:

Tackle your most urgent problem first. Focus on onboarding only when you need to.

Here are some scenarios in which I would AVOID spending time and resources on
onboarding emails and put my efforts elsewhere:

You have a self-serve, free trial SaaS with a visitor to trial conversion rate below 5%

For example:

As a brand new startup, our funnel at Encharge is far from optimized.

Our site visitor to trial Conversion Rate is currently hovering at around 4% for our homepage
and 1% for the total aggregated site traffic.

Not great!

Considering 100% of our revenue comes from our free trials, we need to invest all of our
marketing time on figuring this step of the funnel before we think about optimizing our
onboarding emails.

3
You monthly churn rate is 10% or more

If you have enough data to calculate the churn rate for your business, and if it is 10% or
above, you have a bigger problem than onboarding.

At that rate, you’re churning your whole customer base in less than a year. I would focus on
retention and not customer activation or acquisition.

Your customers are not using email

Since you’re reading this article, I would assume this is not the case with you, but I had to
include it.

If you’re selling to restaurant owners or a B2C audience that doesn’t have the habit of
opening their inbox, you should rethink email onboarding and dabble with other channels
such as Facebook Ads and SMS.

2. What’s the Goal of Your Onboarding Email Campaign?

Now if you’re absolutely convinced that you need to improve your onboarding emails, the
next step is to figure out what your goal with them is?

- Increase conversion rate (i.e., convert more trials to paid customers.)

- Schedule more demo calls with qualified leads.

- Add more new MRR

- Increase ARPU (average revenue per users)

These are a good starting point, but you need to quantify them.

How many trials do you convert monthly, and how many you need to convert to reach your
revenue goals?

This is where most SaaS companies are looking for sanity checks and industry benchmarks.

There are some great resources on the topic from Lincoln Murphy like this post on
benchmarks.

Generally, and this is from my own experience, the best SaaS companies
with opt-in Free Trials see a free trial-to-paid conversion rate of > 25%. Less

4
 than 25% and we know we have to work on optimizing for conversions.



More than 25%, further conversion optimization may result in diminishing
returns on that effort, which means you’d likely be better off working to get
more prospects into the trial, as well as focusing more on expansion (upsells,
cross-sells, etc.) to grow revenue.



Best in class SaaS companies with opt-out Free Trials should have free-to-
paid conversion rates of > 60%. The same rules about optimization apply
with this type of trial, too. – Lincoln Murphy

SIDENOTE: 



Opt-in Free Trials = Trial users don’t leave their card in the signup process.

Opt-out Free Trials = You ask users for a credit card in your signup process.




Personally, I’m not a big fan on comparing yourself against benchmarks.

Using data from others to ascertain your own performance – is fraught.

Differences in site design or digital analytics tool implementation make
comparison shaky – Tracy Rabold, Digital Analytics Consultant at E-Nor

My approach to defining goals usually narrows down to a simple backward calculation.

Let’s say our goal is to convert trials to paid customers.

Based on our current funnel metrics, how many people do we need to convert from a
free trial to a paid subscription in order to reach our weekly/monthly revenue goal?

For example, let’s say our ARPU (Average Revenue Per User) is $50, and we need to
acquire 10 paying users this month to reach our monthly recurring growth goal of $500.

1. We currently get 1,000 monthly website visitors to our website.

2. Of those 7% (70) convert to trials.

3. This means we need 14.3% conversion rate from trial users to paying users to
reach our goal of 10 paying users for the month.

5
At the moment, we’re only converting just 5 people from trial to paid, which means our
Onboarding Goal would be to double that conversion.

I know this is oversimplified, but I believe it’s way healthier than measuring yourself against
others. 



As you now know that you need to to get twice as many people to convert, it’s also easier to
work out your email open and click-through rates goals.

Other example goals include:

- Increase your demo calls from onboarding emails with XX calls per month.

- Increase qualified leads with XX%

- Increase ARPU with XX% (for example: by onboarding/activating more team

members in the onboarding phase).

3. What’s the Desired Outcome of Your Onboarding Emails?

Now forget about your goals, and think about your users’ goals.

What’s their biggest problem?

- Lead generation takes too long.

- Marketing automation is too difficult – it requires development resources.

- Slow email communication.

How your product solves that problem and delivers value?

- People will find a new lead in 15 seconds instead of 2 minutes.

- People will be able to set up their marketing automation system without a

developer.

- Teams will always be on top of their tasks, and their clients will have peace of
mind that everything is delivered on time.

6
Then map out the ”Aha” moments in your product when a user recognizes and
internalizes that value.

Example:

Buffer is a social media management tool, that lets you easily schedule
social posts into the future. Buffer makes this value quick to internalize by
prompting users with the "Add to queue" button by default (over instantly
publishing a post) to help them reach "Aha!". – Pulkit Agrawal, Chameleon

Understanding your users’ problems and your product value will help you identify the main
bottlenecks that prevent the user from reaching these milestones (or Aha moments).

Automated onboarding emails can help your users reach these milestones through different
levers:

- Get your users where they are and pull them back into your product. – if
someone signs up but never touches foot in your app, the best in-app
messaging and in-app onboarding flow won’t help you. Email, on the contrary,
can pull the users back pretty swiftly.

- Increase user motivation to proceed further along your onboarding

process. – by picturing a better world through case studies and positive
affirmations, onboarding emails can nudge your trials or leads to move forward
in the onboarding flow.

7
 - Reduce user experience friction by reminding people of the next most
critical action – trigger or action-based emails can remind people to continue
where they last left your app and help them focus on the most essential
features in your product. Super important, especially if you have a more
complex SaaS.

Apart from that, onboarding emails are helping us get as much information as we can,
especially from users who are leaving (or more likely to leave). Information that we can use
to iterate on our onboarding flow.

By knowing what’s the desired outcome of your users and the roadblocks they experience in
your app, you can facilitate your users through your onboarding emails.

8
Understand Where Onboarding Emails Fit in Your
Customer Experience

Your onboarding email campaign is just a part of your onboarding flow. Onboarding emails
should serve as an extension of your product, not a siloed element.

To create a cohesive onboarding strategy, use The Bowling Alley Framework.

The Bowling Alley framework is a powerful onboarding strategy I learned from Wes Bush,
author of the “Product-Led Growth” book.

If you never played bowling before, this is what the sports look like:

You throw a heavy ball towards 10 pins that stand at the end of a lane. The goal is to knock
over all of the pins.

It sounds pretty simple, but there’s just one issue: there are gutters on the edges of the lane.
If your ball falls into the gutter, you won’t knock any pins.

To make life easier for bowling rookies like me, a smart bowling guy invented the bowling
bumpers which keep balls from going into the gutter.

According to Wes, in the world of Customer Onboarding, bumpers guide your users to the
outcome that your product promises:

9
 

Diagram from “Product-Led Growth” book by Wes Bush

There are 2 types of onboarding bumpers:

Product bumpers – in-app experiences like product tours and tooltips. They help users
adopt product usage in the application itself.

10
 

Behance In-app checklist

Product bumpers include:

- Onboarding tours

- Checklists

- Tooltips

- Progress bars

- Empty placeholder states

11
 Conversational bumpers – in-app messages and onboarding emails.

Example in-app message from Intercom

Conversational bumpers include:

- In-app messages from a tool like Intercom or Appcues

- Push Notifications

- SMS

- And of course onboarding emails

As you can see, emails are just a part of your whole onboarding process; therefore you need
to decide how they’re going to work with the rest of the bumpers to create a smooth
onboarding experience and set up users to success with your product.

12
Design Your Email Onboarding Campaign

OK, so far:

1. You’ve decided what your goal is.

2. And planned how to incorporate emails with the rest of your onboarding flow to
get the best results.



The next step is to start planning out your actual email onboarding campaign.

How Many Emails To Send and When?

First, you have to decide how long your email onboarding campaigns is going to be, how
many emails you’re going to send and when.

There’s no single one-size-fits-all answer.

The factors to consider are:

- Your business model - free trial, freemium, or high-touch sales.

- The length of your trial - 7 days, 14 days, 30 days or more.

- Whether you’re going to have self-serve or sales-assisted onboarding.

A post by MadKudu sheds light on a couple important observations:

It takes about 40 days to get 80% of SaaS conversions

13
 

Regardless of trial length, people need up to 40 days to pull a trigger on a new SaaS.

But as you can see the 14-day trial (purple line) has a bigger spike in the beginning – more
people are converting faster – compared to a 30-day trial. Which is expected.

Half of SaaS conversions happen AFTER the trial ends

A free trial creates artificial purchasing urgency. But there isn’t anything
magical about the last day of a trial – some customers continue to convert at
their own rate based on incentives or their perceptions of value. – Mad Kudu

Onboarding emails are not the END of your onboarding – a lot of your users will come back
to your product long after they’ve exited your email onboarding flow. In fact, MadKudu
mentions that most companies had customers converting 6 months after signing up. (Insane,
I know!)

Moreover:

In a research report by Oracle from 2014, it was found that on average the
first 90 days of the customer lifecycle are the most volatile. Apparently, this is
when banking customers are most likely to churn, and up to 30% of
customers are susceptible to competitive offers. – ConversionXL

14
Emailing your leads (and paying customers alike) in the first 90 days after they signup is
absolutely necessary.

A case study by Returnpath solidifies these observations by stating that:

Subscribers are generally most receptive to your marketing messages within

the first 30 days of opting into your program.

Longer trials don’t lead to more conversions

Tomasz Tunguz, managing partner Redpoint Ventures, recently shared in a report on 600
SaaS companies that conversion rate is same across trial lengths.



In other words, giving people more time to test your product would not make them more
likely to convert.

There are a few conclusions that we can make drawing from these stats:

1. Shorten your trial length – 7 to 14 days is the golden range. Trial length
doesn’t alter conversions, but shorter trials create a momentum which leads to
higher % of your trials converting faster.

2. Send more emails at the beginning of your onboarding – Recency in your

emails is crucial. To accelerate sales, and increase conversions, you have to be
aggressive with your email marketing in the first days of the user lifecycle.

15
 3. Engage your users after the trial ends – Pursue post-trial sales and expand
your email campaign beyond your trial period.

4. Employ action-based emails – Time-based emails are useful but are not
going to do much for that fraction of your trials that don’t convert within the trial
period. Target users based on qualification and behavior and pursue them
aggressively with trigger-based emails. For example, when a user logs in after
a long absence, re-engage them using a trigger-based email.

Here’s an example schedule that you can use for your onboarding email campaign:

This schedule is on the more aggressive side, and you should reduce accordingly if your
audience is not used to receiving (many) emails.

The take away here is that the first 30-40 days of your user cycle are crucial and you
definitely want to email your leads at least 90 days after their signup.

Self-serve Only VS Sales-Assisted Onboarding

In other words, should you expect people to onboard themselves or help them with demos
and calls / hire salespeople to call your trial leads?



The short answer is – it’s better if you assist users in your onboarding.

Citing more stats from the report by Tomasz Tunguz:

75% of SaaS companies have salespeople contact Freemium leads

There is a reason. Assisted conversion rate is almost 4x that of self-serve conversion rate:

16
 

What does that mean for your email onboarding campaign?

You need a sales-touch email flow.

Sales-touch emails take the form of personal emails that you send to your trial users in order
to help them with your SaaS, get them to book a call, etc. More on that in the next chapter.

Who Is Going To Send the Onboarding Emails?

It’s also important to consider who’s going to send the emails – the founder, account
manager, support, etc.



Most marketing automation platforms like Encharge support multiple sender profiles. That
way, you can send an onboarding welcome email from your founder and any further emails
from the customer success team, for example.



Also, make sure you’re using real reply-to emails and checking your inbox regularly! 


Important note: Do not send onboarding emails from a no-reply email.

17
Onboarding Flows

Your onboarding email campaign is built of multiple email flows or email sequences.

There are different types of onboarding flows that you can implement:

1. Welcome Flow

2. App Usage Flow

3. Expiry Warning/Trial Extension Flow

4. Sales-touch Flow/Customer Success Onboarding Flow

5. Post-Trial Flow

Each flow serves a different purpose in your email onboarding campaign.

You can also mix these flows to create hybrid-flows.

It’s totally fine to start with a single onboarding flow (or one that mixes emails from all flows)
but as you progress you should aim to make your email onboarding more sophisticated.
Unless you’re already pleased with a single flow or your users are allergic to getting many
emails.

18
Continue reading because we’ve dedicated a chapter for each of these flows.

If you’re at a loss for words, don’t worry! We’re going to provide onboarding email examples.

You can start with any of these email sequence templates that we’ve created for you.

19
The Welcome Flow

The welcome flow is triggered as soon as someone signs up for an account.

It’s usually a time-based sequence that consists of a Welcome email, Product tips, Case
studies, and CTAs to upgrade.

A typical structure for a Welcome flow for a 14-day trial could look like this:

- Day 1: Welcome email

- Day 3: Product tip 1

- Day 5: Product tip 2

- Day 7: Case study 1

- Day 10: Product tip 3

- Day 12: Case study 2

- Day 13: Case study 3 + CTA to upgrade

Let’s explain each email in the Welcome flow.

Welcome Email

Goal: Train your users to open your emails and clarify what they expect in the trial period.

When to send: As soon as a user signs up.

Your welcome email is going to be the email with the highest open rate in your onboarding
campaign. It’s realistic to expect 30-60% open rates.

Given the high engagement of that email, you might be tempted to include a lot of
information and multiple aggressive CTAs in it. This is the wrong approach.

The purpose of the welcome email is to set the right expectations and introduce people to
your software. It also needs to have just one CTA.

Example Welcome email:

Encharge.io Welcome email

20
Subject line: Welcome to Encharge, Name!

21
We’re currently getting a 46.3% open rate and a 6% click-through rate on this email.



🔥 What’s good about this email:

- Personalized subject line. (Notice we’re also using liquid tags to avoid awkward
blank spaces for leads with missing names)

- Benefit-oriented overview of the product. Just because people have signed up

for your product, don’t expect they understand or remember what it does. The
welcome email is your opportunity to reaffirm your product’s value.

- Sets the right expectations.

- A simple CTA that gets users back in the product.

💩 What can be improved:

As a new company, maybe we should focus on collecting feedback in our very first email and
ask people why they’ve signed up for Encharge (it’s something we do in the next email in our
welcome flow).

Product Tip Email

Goal: Provide value-based product information and nudge the user to complete the next step
in the onboarding.

When to send: Depends on your onboarding email schedule, every other day is OK.

It’s ludicrous that as marketers, we get so obsessed about user acquisition that amidst this
disproportionate emphasis on getting more leads, trials or whatever we forget to educate
people when we actually have their attention. Use the welcome flow as an opportunity to
help people be more successful while highlighting the key features of your app.

Wix.com Product Tip Email

Subject line: Pro design tips for your site

22
 

🔥 What’s good about this email:

- Ridiculously simple and easy to read. The short tips combined with bullet
points would make scanning this email a breeze.

- Practical yet benefit-oriented. The email presents the high-level benefit “stand
out” and “look professional”, while providing the solution. And all that in less
than 50 words.

23
 - A call to action button that stands out.

Including a call to action button instead of a text link can increase conversion
rates by as much as 28%. – Campaign Monitor

💩 What can be improved:

A bit more personalization would definitely promote engagement here. Take out the generic
“your website” and swap it with a merge tag with the name or domain of the receiver. “4
Professional Design Tips for Encharge.io”, for example.

Case Study Email

Goal: Handle any objections trial users have and provide social proof.

When to send: Depends on your email sending schedule, every other day is fine.

So far, you’ve been sending emails from you and your team. Now it’s time to ket others sing
your praises and address common objections your trialing users have.

It doesn’t need to be a full-blown, in-depth case study. You can use one of your 5-star
reviews on G2Crowd, a video testimonial, customer story, or even a conversation you had
with a happy customer on your live chat.

Airtable Use Case Email

Subject line: New York City Ballet's golden ticket

24
 

🔥 What’s good about this email:

- The email body emphasizes the sheer amount of data “hundreds hours of
footage and marketing collateral” that their client is dealing with, which alludes
the power of Airtable.

💩 What can be improved:

- This email needs a lot of work! First of all, taking into account the broad
audience of Airtable that spans across hundreds of industries and verticals, the
subject line doesn’t give up even a vague indication that this is going to be a
case study for the tool.

25
 - The body copy doesn’t help either. It lacks any concrete information on how
Airtable improves the workflow of their customer.

- It also lacks any social proof or objection handling.

- On closer inspection, the actual case study contains powerful quotes that could
fit very well in the email and provide more context:

In your case study emails, you’d want to pair one or more of your top objections with a case
study or testimonial. The most common objections among SaaS customers (or in business in
general) are:

1. I don’t need it.

2. It’s too expensive

3. I don’t trust it/you.

4. I’m not in a hurry to buy it.

Call to Action Email

Goal: Get people to pull the trigger on your trial.

26
When to send: 1-3 days before the trial ends or on special occasions

Every email you send ever needs to have a call to action (CTA)! So don’t get me wrong, you
don’t need a separate email to get people to upgrade or purchase a subscription. In fact, you
should sprinkle in upgrade CTAs anywhere from the middle of your welcome flow until its
end.



Yet, your onboarding is no time to be shy. A bit more aggressive ask for commitment is not
going to hurt your conversion rates.

Headspace Call to Action Email

Subject line: 3 ways to make your summer better

27
 

28
 

🔥 What’s good about this onboarding email:

- Gorgeous graphics! Headspace has one of the most beautiful set of animated
GIF illustrations I’ve seen in my inbox.

- A distinct and clear call to action (this is the whole purpose of the email after
all?)

- Solid social proof - “Join the 50 million people”

29
 - A straightforward summary of what I’m getting with Headspace Plus

- With this little blurb at the end of the email, Headspace is taking away the fear
of buying a new app just to find out that you don’t know to use it later:

💩 What can be improved:

Headspace is a seasoned player on the app market, and as marketers, we have a lot to
learn from them. My only humble critique for this email is that as a user I wished the subject
line indicated somehow this is going to be an upgrade email. Also, a mention of their pricing
would help me make up my mind if I want to click on the email.

NEXT STEPS:



Register for Encharge and use these welcome flow templates with a single click:

- Onboard Trial Users and Help Them Reach the "Aha" Moment

- Convert Trial Users With Targeted Onboarding Campaigns

30
The App Usage Flow

The App Usage Flow consists of trigger-based emails, also known as event-based or action-
based emails.

These emails get sent according to a user’s activity in your app (or lack therefore of).

What separates mediocre onboarding campaigns and unrivaled, effective, onboarding

campaigns is indeed the app usage flow.

Building an app usage flow takes deliberate planning with your development team and
additional effort. That’s why most companies don’t incorporate a trigger-based email
sequence at all.

This is a huge missed opportunity for you and your business.

Source: WebFX

Setting up trigger-based emails is tough. Everybody knows they need to do it, but nobody
wants to do it.

That’s why we spent the last year building Encharge. We aim to solve this problem with easy
native app integrations, powerful user segmentation, and the drag and drop simplicity to build
effective app usage flows without a developer. Read the end of this chapter to find out how to
set up Encharge for trigger-based flows.

31
 

A simple trigger-based flow in Encharge – Send an email when a user becomes a trial

Trigger-based emails help you send the right message to the right people at the right
time on the right channel. Their purpose spans beyond onboarding and you’re going to use
them across the whole customer lifecycle communication – from product adoption to
retention and upsell.

The possibilities for what emails to include in your app usage flow are endless, and you can
literary create any type of trigger-based emails, as it all depends on your product user
experience. Therefore, we can’t feature every single trigger-based email, but we’re going to
give you 4 use cases that are especially helpful in the onboarding phase of the customer
journey.

1. Motivate Users

2. Highlight the progress your users have made

3. Provide Proactive Support

4. Push Unfinished Registrations to Complete Signup

32
Motivate users

Goal: Incentivize new users for exploring your product and

When to send: After a user completes a specific action in your product successfully

People are hardwired to seek rewards. Every time someone likes or comments on your
Facebook posts, Facebook is giving us a little dopamine hit.

Now I don’t ask you to become a little marketing genius that exploits human psychology to
control people, but a little reward here and there can undoubtedly help your conversion rates.

You can use the motivation email to reward users of exploring your product and completing
crucial steps, that way leading them to the desired Aha moment.

Ascend Motivational Email

Subject line: Your First Email Campaign Is Live

33
 

🔥 What’s good about this email:

- Ascends celebrates an important milestone in the user experience of their tool

with a cheerful email and also provides guidance about the next steps.

34
 - They give me enough inspiration for my email broadcast and a concise call to
action button that pulls me back in that feature of the tool.

- Towards the end of the email, I can see a list of actions related to my email.

💩 What can be improved:

If Ascend included the person’s name or the title of the campaign, the person would’ve been
more convinced that this is a special “reward” for them and not a cookie-cutter email Ascend
sends to everybody.

Highlight the progress your users have made

Goal: Create a feeling of progress and nudge people to move forward in your onboarding

When to send: After a user completes one or more actions in your app

In 2004, marketing researchers Joseph Nunes and Xavier Dreze teamed

with a local car wash in a busy metropolitan area. 



For one month, the researchers handed out loyalty stamp cards.



They used two different cards depending on the week:



- Customers on the first and fourth week received a card with an offer to “buy
eight car washes and get the ninth one free.” 

-The second group of customers received a card with a slightly different offer.
They were awarded one free wash for every ten purchases, but they were
also gifted two free credits.



In absolute terms, each deal was the same. Eight trips to the car wash
earned one free wash. Yet twice as many people in the second condition
completed the stamp card; having earned two credits, the feeling of progress
nudged them to return. – To Create a Habit, Focus on the Reward,
TechCrunch

Nunes and Dreze term this tendency the endowed progress effect:

We’re more committed to completing a goal when we have made some progress.

Autopilot Example Email

35
Subject line: Account review

36
🔥 What’s good about this email:

Autopilot is a competitor of ours, but we give credit where credit is due. They’ve come up
with a brilliant onboarding progress email. The Autopilot “account review” gives you a
checklist of what you’ve completed and whatnot in your onboarding. When you complete an
action, the ❌ becomes a ✅

💩 What can be improved:

This email is personalized, provides context, and presents dense information in a simple
way. The only thing I’d play around with is A/B test the subject line “Account review” with
something more inspiring like “Kaloyan, see the next steps for success with Autopilot.”

Provide Proactive Support

Goal: Identifying and resolve users issues before they become problems.

When to send: When a trial user visits your help desk multiple times; or is half-way through
a step in the onboarding process

Reactive customer service:

A customer is browsing your SaaS and has a question or issue. Typically, they find a live chat
button or email you and wait for a response.

Proactive customer service:

It means anticipating customer problems and addressing them proactively.

Email is a great way to address user roadblocks in advance, and with marketing automation
tools like Encharge that provide advanced segmentation based on events, this can even be
automated.

For example, if a user visits a particular page on your knowledge base more than 2 times in
less than a week, it’s worth checking with them if they need help.

Podia Proactive Support Email

Subject line: Need some help connecting your Stripe account? 🔧

37
 

🔥 What’s good about this email:

Rather than just asking if you need help, this email actually highlights the reason why you’d
like to integrate with Stripe while also handling the objections of transaction fees and waiting.
Clever!

💩 What can be improved:

Instead of stating that you can message them on live chat, I’d include a link to a contact
page, or even better – the Stripe integration page that automatically opens an Intercom live
chat window (possible with a Javascript). In that way, guiding the user to the right location in
your app while providing them with an immediate 1-click live contact.

Push Unfinished Registrations to Complete Signup

Goal: Get people back in the app and nudge them to finish their registration

When to send: When a user starts a registration process but doesn’t complete it

This flow is activated before a lead becomes a registered user of your product.

For example:

When in a 2-step registration process that consists of Step 1. User details and Step 2. Billing
details – the user completes the first step but drops off before filling in their billing details.

38
Grammarly Unfinished Registration Email

Subject line: Writer’s Block? We’ve Got an App for That

🔥 What’s good about this email:

- You will receive this email if you signup for Grammarly but never install their
Chrome extension. Rather than just pushing you to complete your registration,
Grammarly actually reminds you, “Why you need this again?”

39
 - Notice how they’ve combined the progress type of email with this unfinished
registration email to create a sense of momentum and handle the objection of
dealing with a long-winded signup process.

💩 What can be improved:

This email would benefit from a clear call to action like “Install Chrome Extension.”

NEXT STEPS:

1. Register for Encharge

2. Bring your user and customer data in Encharge. We support native integrations
with Segment, Stripe, and Zapier, but you can also integrate with our API

3. Use one of these app usage flow to get your creative juices flowing:

- Educate Users About a Recently Activated Feature

- Push Unfinished Registrations to Complete Signup

- Revive Dead Product Leads

- Follow Up On Pricing Page Visit (you can substitute with a follow up on a visit
to a knowledge base page instead and send proactive support message)

Step 4: See your trial to paid conversions skyrocket! 




You can also contact us to brainstorm and set up your behavior-based emails for you.

40
Expiry Warning/Trial Extension Flow

Expiry warning and trial extension flows are other great tools in your onboarding arsenal.
They leverage the inner psychological triggers of scarcity and urgency to help you convert
more of your users into paying customers.

Expiry Warning Email

Goal: Let the users know they need to act quickly and immediate action should be taken

When to send: Send 24 - 72 hours before the trial expires

Urgency has everything to do with timing. It’s pointless to flood someone’s inbox with
warnings about a trial expiration before they have started exploring your product.

Typically, you’d want to send the expiration emails 1-3 days before the trial is over or 1-7
days if you have an extended trial (20-30-day trial).

At the last day of the trial, you’d want to send a trial ends email. The sole purpose of this
email is to close the lead. It’s your chance to illustrate what life would look for the trial user if
they don’t upgrade now (clue: life is worse without your software.)

There’s nothing that motivates people more than telling someone what they’ll
miss out on. In psychology, it’s called loss aversion.



So ask yourself:



What will users miss out on if they don’t upgrade to a paid plan?

Sophia Le has written this brilliant article on CopyHackers dedicated to the trial ending email.

Upscope Trial Expiry Flow

Subject line: ⚠ Your trial ends soon!

When: 3 days before trial is over

Clickthrough rate: 6%

41
 

Subject line: Trial ends tomorrow

When: 1 day before trial is over

Clickthrough rate: 5%

Subject line: Your trial has ended 😢

42
When: Trial ended

Clickthrough rate: 6%

You can review the whole Upscope email campaign on their blog.

🔥 What’s good about these emails:

A simple, clear call to action combined with great timing.

💩 What can be improved:

- Not a huge fan of sending emails from the Team’s email account. Stick to your
personal emails.

- Each email you send is an opportunity to reaffirm the value of your product.
Don’t expect that just because people have reached the end of your trial, know
what the product can do for them. Life happens! 



“The reality is your free-trial user signs up for a trial… and then heads back into
a massive, endlessly explorable digital and physical world, filled with rock-
climbing classes and sangria-on-patios and deadlines and Facebook and
existing processes and people and shiny distractions and shitty distractions… “
– Sophia Le



A simple “I really don't want you to miss on [Product] and [high-level benefit].”

43
 could go a long way. For example, “I don’t want you to miss on Upscope and
the opportunity to reduce onboarding team's call time by 27%.”

- In the trial ending email, Upscope has missed the opportunity to emphasize
what life will look without their tool – prolonged support conversations, lack of
qualitative data, longer support ticket response rates, and so on.

Trial Extension Email

Goal: Provide one last opportunity for people to test your product before they get locked out
of their free trial

When to send: Send 24 - 72 hours before the trial expires

There’s little reason in sending scarcity emails to people that haven’t used or opened your
software.

Urgency starts with importance.




In order for something to be urgent it has to be important. Think about a man
selling helium balloons at a golf course. He can’t really use urgency to sell
his balloons, because no one at a golf course needs or wants a helium
balloon. – Crazy Egg

You can create a trialing segment of people that have been inactive in your app and offer a
special extension for them.

Squarespace Trial Extension Email

Subject line: Your trial ends tomorrow

44
 

45
🔥 What’s good about this email:

- A little touch of personalization – Squarespace has included the name of the

website

- Squarespace doesn’t assume the user knows what SquareSpace is just

because he reached the end of the trial sequence. The second paragraph
describes what Squarespace is while also describing some of their top
features.

- Without putting too much pressure on the user, Squarespace reassures that it’s
totally OK to give the tool some more time.

💩 What can be improved:

I would break the trial extension and trial ending emails into two separate emails, and send
the extension email only to inactive users. With your trial ending email, you want to keep it
simple and close the deal ASAP, not provide an excuse for the already active users to delay
the purchase. The old sales axiom “Time kills deals” is also true in SaaS.

46
Sales-touch Flow/Customer Success Onboarding
Flow

Sales-touch emails are personal emails that you send to your trial users in order to engage
them in a conversation with you.

The purpose of these emails is to ultimately convert trials to paying customers but without
being “salesy”. Think of sales-touch emails as an opportunity to advise people, collect
feedback, and book success calls with potential leads.

Sales-touch emails should be personalized and create the notion that you’re sending them
manually.

To get higher engagement, you can also follow-up on your sales-touch emails whenever you
don’t receive a reply.

Sales-touch emails can be time-based or trigger-based. Here are a couple examples that
you can use in your onboarding campaign:

Personal Introduction Email

Goal: Introduce yourself as a real human, collect viable customer feedback, or get the
person to book a demo call with you.

When to send: 1-24 after the signup. To make it look a bit more personal, you can delay
sending this email a few hours after user registration.

This email is very similar to the welcome email but puts a human touch to it. The goal is to
start a conversation with your trials.

This iconic example from GrooveHQ has been making the rounds on the web. I’m not going
to lie that I’ve copied its structure in my previous startup HeadReach, as well as Encharge.

47
 

Onboarding emails usually don’t get a whole lot of responses. This is not the case with the
personal intro email. By asking the crucial question: why did you signup?Groove were able to
collect tons of customer data without doing anything more than setting up this automated
email.

Demo Call Email

Goal: Offer a demo call and personal help for trials

When to send: 1-24 after the signup or whenever a user shows an indication of being stuck
in the product

Frame these emails as “success calls”. Your role as a product advisor is to help people get
more out of your product or orient inactive trials.

This sales-touch onboarding email from GatherContent asks people if they need help but
also incentivizes them to jump on a quick chat by offering a quick “sneak peek” into new
features. Who wouldn’t want to feel special by being the first one to see the new features?

48
 

49
Post-Trial Flow

This is the last type of onboarding flow we have, so congratulations on reaching that far!
You’re a real marketing automation warrior.

Remember when we said that half of the sales in SaaS actually happen after the trial period
and you should pursue post-trial sales. Well, the post-trial onboarding flow is your opportunity
to:

1. Ask for feedback.

2. Offer a discount to your ex-trialists.

3. Continue nurturing them with valuable content and materials.

Post-Trial Survey Email

Goal: Understand why trialing people didn’t buy

When to send: 1-3 day after trial expires

This email collects information about why people didn’t buy and helps you craft a better
onboarding experience or improve your product. It also gives you a second chance to
convert your trials by addressing the right objections and fixing any highlighted user
problems in your future win-back emails.

Instapage Post-Trial Survey Email

Subject line: A Quick Question from Instapage

50
 

🔥 What’s good about this email:

Simple, plain design with a prominent call to action.

💩 What can be improved:

People loathe filling in surveys. To handle this objection, Instapage can include a little tip that
this is a single-question survey, and it will take me less than 20 seconds to complete.

51
 

Once you know why people don’t buy, the next step is to address the reasons by putting
people in a relevant marketing automation flow (hint: you can use Encharge for this, too)

- I'm using another solution to create landing pages > Send to a nurturing flow to
stay top of mind when they decide to churn from the other tool.

- Instapage is too expensive > Offer an exclusive one-time discount.

- Instapage is too difficult to learn > Start a sales-touch flow offering a 30-minute
free crash course with a product success hero.

52
 - Instapage is missing features I need > Inquire about the feature, or ask the
person to submit a request in your feature request software. Let them know
when the new feature is live.

Post-Trial Discount Email

Goal: Pull-back in good fit trials with a money objection

When to send: 1-3 day after trial expires

This email tries to convert active people that find your product expensive.

Attracting cheap, unqualified customers is a recipe for high churn and long support
conversations. You should reserve any discounts only for people that are a good fit for you.



Discounts are especially effective for high-margin, low-expense apps like Headspace.

53
 

1. At first, Headspace asks me to buy the app at their shelf price.

2. 9 days later they offer 25% off.

3. Then, 5 days later a follow-up on the 25% off deal.

4. As a last resort, they offer 40% off 3 days later

5. Aaand a follow-up 2 weeks after that.

Check out our expired-trials flow by registering for Encharge.

54
 

55
Further Reading

- 13 Email Sequence Templates to Convert More Leads, Increase MRR &

Reduce Churn

- The Essential Guide to Marketing Automation for SaaS

- Marketing Automation Strategy Workshop

56
Onboarding Email Resources

- Top 10 Learnings about Free Trials with Tomasz Tunguz

- Are Your Free Trial Emails Making You Look Desperate? Here’s How to Fix
That

- 7 Customer Onboarding Email Templates That You Can Use by Groove

- The onboarding campaign Upscope used to double their installs

- How CopyHackers tripled paid conversions of Wistia’s onboarding

- Here Are All Of The Emails We Send At Drift – includes onboarding emails

- The Killer Strategy Behind Our New User Onboarding Emails by ProdPad – the
team at ProdPad share how they use “magically extending free trial” to reward
users with more free trial time for completing in-app actions.

- How We Increased Engagement for Our Onboarding Emails by 1213.3% by

Sleeknote – note: this case study is actually for a blog onboarding sequence,
which usually tends to go by the name of a “nurturing” sequence. Nevertheless,
well worth the check for the clever use of segments and their impressive open
rates.

- Onboarding Emails Inspiration by Really Good Emails

57