1.

George Gallegos, CEO, Jitterbit

"On an important call late in the sales cycle, negotiations were getting

intense. Neither side wanted to back down from the numbers that had been

shared. But at a crucial point in the conversation, the party we were selling

to forgot to hit the mute button on their conference line. We overheard

them raving on and on about how much they liked the product, and we

knew they were completely sold. Knowing this gave us the leverage we

needed to close the deal on our terms. The moral of the story? Always

check that mute button; it could save you some money."

2. Steve Ackley, vice president of

sales, Altiscale
"In the late 90s, I was working for Tivoli Systems, which had just been

acquired by IBM, and was working on a deal with Charles Schwab. At this

time, enterprise software

sales representatives always wore suits and ties, even on Fridays. We were

actually

much more formal than other parts of the country. However, while my first

Charles Schwab meeting cemented our relationship for the deal, it also

challenged my wardrobe choices. To my surprise, when I entered the

meeting at Charles Schwab, they claimed it was a 'no tie zone' and
proceeded to cut off my tie and pin it to the wall. Ultimately, we closed the

deal (my biggest yet), which resulted in the ongoing joke that I could now

afford to buy a new tie."

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3. Hans Geiszler, founder, Japhy Surf Co.

"When I first started my board short company, Japhy Surf Co., a television

producer friend of mine from New York said she had an opportunity for

me. She said she was putting together a new series focusing on young

entrepreneurs and that I would be pitching to a group of investors who

would decided to invest or not--think Shark Tank. I decided I had nothing

to lose, so I cruised from San Francisco to the Big Apple to pitch a board

short company in negative-5 degree weather. I put on a suit and tie and

went down to the studio. As soon as I got there, I saw that everyone had

done the exact same--cleaned up and put on the same exact navy or grey

suit for their pitch. So, I decided to throw a Hail Mary. I stripped down,
threw on a pair of my trunks, lost my shirt and tie, and got down to bare

feet. When I walked onto the set, the producers immediately lost it

laughing--'What are you thinking rolling around in swim trunks? It's

snowing outside, you lunatic!' I proceeded to give my pitch. The investors

were either completely sold, or just took pity on the clown standing in

front of them, but they all decided to invest!"

4. Jane Riley, director of sales

and operations, eH+ by eHarmony
"I have always considered myself a tough and well-seasoned negotiator.

Having spent most of my career in sales, I have negotiated everything

from multimillion dollar real estate transactions to terms of service for

eH+ premium matchmaking. I have gone head-to-head with some of the

best CEOs and COOs in the business, but my most formidable opponent is

still my 4-year-old daughter Jillian. Her ability to be both charming and

contriving while also vehemently refusing to eat her vegetables is a skill

unlike any other. Her negotiation prowess is unmatched, especially at nap

time. Negotiating with Jillian and her little sister Lilly has taught me to be

patient, empathetic, and open-minded, and has made me a stronger

negotiator and more appreciative parent."

5. Andrew Peterson, CEO, Signal Sciences
"In college, I worked in retail sales at The North Face, and my favorite

customer interactions were always the ones when I'd recommend the

customer go somewhere else. Don't get me wrong, I loved The North Face

and all of their products! But I was always more intent on getting the

customer the best product for what they were looking for. When that

wasn't something from our company, I'd tell them what they should get

instead and where to get it from. Funny thing was, they always ended up

buying at least something from me because they were so shocked I wasn't j

ust

pushing our products on them. A great lesson I learned from this is that the

best salespeople are the ones you trust."

6. Richard Nieset, chief customer officer, Pixlee

"Early in my sales career, I got assigned one of our team's most

'challenging' accounts. The account had been a big customer in the heyday

of the Texas oil boom, but most of the glory had died down by the time I

got there. Everyone in the office laughed into their beers when they heard

where I'd been assigned. One colleague told me, 'Yep, that contact is a

pain in the butt. He'll keep you hoping, but don't expect much.' I got many

requests from that customer contact, and did everything I could to

prioritize helping him with his asks. I figured we would have a big order

by the end of the month; but when the time came, there were some

rumblings but no orders. So, since I was in Texas after all, I naturally went

to Toys 'R' Us and bought a toy six-shooter and the six bullets that come

with it. I handed the gun to the customer I was working with at our next in-

person meeting, along with six bullets, and explained what was going to

happen. Here was my deal: He could ask me for anything he needed from

us and anything we could possibly do, we would do. But each time he

asked, he had to give me one of those bullets. When I got all six bullets, I

would get to ask for something in return, and you can probably guess what

that was going to be. Eventually, I got him to agree, leading to one of the

largest deals in our company history. It probably had nothing to do with

the bullets, but it's still one of my favorite stories."

7. Julia Jacobson, CEO and co-founder, NMRKT

"I have this problem--it's like dyslexia for common sayings. Even phrases

I've heard a thousand times come out of my mouth scrambled. During our

biggest sales pitch to date, my co-founder and I walk into the corporate

offices of our dream customer with every detail of the pitch squared away.

Everything is going great. We nailed it. A couple hours later my co-

founder Slacks me...'There was something you said in the meeting...' In my

excitement, I had blurted out, 'You will be playing yourself at a

disadvantage with our product' instead of saying either 'playing to your

advantage' or 'setting yourself up for a win.' While we got the contract, I

will always be embarrassed about that meeting."

8. Amanda Curtis, CEO and co-

founder, Nineteenth Amendment
"Sales is a lot like fundraising: It takes hard work, dedication, and

commitment, and often times you must go outside of your comfort zone

and take a risk in order to take advantage of opportunities around you.

That's why, when I was invited to participate in PeakPitch, I couldn't pass

up the chance to meet with over 50 marquee investors and pitch... on a ski

lift. The day of the event, I woke up at four in the morning and headed to

Hunter Mountain, where I spent the day heads down, skis up, raising our

seed round on a mountain! In the end, it was well worth it when we won

fourth place out of 85 companies--and the only female-led, B2C company

to boot (literally)."