Last year, I resurfaced an interview I did on the How the Deal Was Done podcast where I broke down the biggest annual contract I’ve ever closed.
A seven-figure agreement with a massive, publicly traded consumer brand.
And the funniest part? It started with an inbound lead from a UX manager.
Not a VP. Not procurement. Not the CFO.
A UX manager.
So if you’re sitting on a deal that feels “too small” or “too low in the org,” keep reading. Because this is the exact type of slow-burn deal that turns into a career-maker if you know what to do with it.
The setup
I was selling for a Series B startup in the contact center space.
Our product helped big brands add messaging channels into their customer experience:
Early stage company. Skeleton crew. Territory was basically the entire US.
At the time, most of the enterprise team had rolled off, so I had the luxury of catching almost every enterprise inbound lead.
One day, we get an inbound from a well-known home services brand.
Household name. You’ve probably seen their trucks driving around your neighborhood.
Cool logo…
But again, the lead came from a UX manager.
So the first few conversations were murky:
- No clear urgency
- No obvious pain
- No big “we need to fix this now” moment
It was a slow burn. A couple intro calls. An onsite at their contact center a few months later.
Nothing that screamed “this is going to be the largest deal of your career.”
Also, this was mid-2020. Peak uncertainty.
Companies were slashing spend. Buying software was not exactly the vibe.
So we took it slow.
The first yes was small
Eventually we landed a small proof of concept.
One channel. One use case. 90 days.
Around $10,000.
Not life changing. Not even quota changing. Just enough to get in the door and prove the product works in their environment.
But here’s where the deal shifted.
That UX manager was a monster champion. The best kind.
He was an internal evangelist who wasn’t afraid to shake the tree, call senior people, knock on doors, and move things forward.
Champions like that are rare.
He pushed finance to cut the initial check, and we kicked off the pilot.
The catalyst: a new CEO and a revenue mandate
Right around that time, the company hired a new CEO.
And like clockwork, the new CEO comes in and says:
Revenue. Revenue. Revenue. They needed growth. They needed profits. They needed the share price up.
Every team was asked the same question:
How are you going to help us drive revenue this year?
Suddenly, our pilot wasn’t “a nice-to-have experiment.”
It became a potential growth channel.Because the use case came into focus. This brand had a database full of millions of inactive customers.
People who used the service in the past, but weren’t active subscribers anymore.
So the question became: What if we use messaging to re-engage those customers?
- Text them an offer
- Text them a reminder
- Text them a promo
- Get them to book again
- Turn dead records into booked revenue
That idea made it all the way up the chain.
And once leadership latched onto it, the deal started gaining traction.
That $10,000 pilot turned into a $150,000 commitment. Then a few weeks later, another $150,000. Now we had real momentum.
Important detail:
This product was usage-based. Not seat-based.
The more messaging volume they sent, the more they paid.
Which is great…
Until your buyer starts asking the next question.
The moment everything changed
During the pilot kickoff, I got exposure to senior leadership.
Director of Customer Service. Then the VP (who later became their Chief Customer Officer).
One of them mentioned he was based in Phoenix. I had just moved to Phoenix. I reached out and asked if he wanted to grab a drink sometime.
He politely declined (pandemic).
But the important part was I had his cell number.
A week or two later, I get a text:
“Give me a call as soon as you can. I have a question for you.” I call.
He says:
“This proof of concept is going really well. Leadership knows about it. The CEO sees this as a revenue channel. We need to scale it. Talk to me about what an unlimited license looks like.”
And I remember thinking: Oh holy shit.
This just became a seven-figure conversation.
The playbook (steal this)
A few things made the difference in this deal, and I still use these plays today:
1) Mobile-first relationships
Email is noisy. Calendars are noisy. Text cuts through when you’ve built enough trust to earn it.
2) Peer executives early
I pulled in our VP of Sales fast, then our founder CEO. Execs want to talk to execs.
3) Get creative with channels
We set up a shared Slack channel between their technical team and ours so their engineers could talk directly to our head of development. That built trust instantly.
4) Speed equals confidence
Real-time back-and-forth meant we could redline, adjust numbers, and keep momentum without waiting a week between emails. From there it was negotiation, compliance checks, tech validation, and a lot of waiting.
They went dark after Thanksgiving. Everyone internally started sweating a bit. They told us if it was going to happen, it would happen before December 31st.
Then on December 23rd, the DocuSign came back signed.
I was already off for the holidays, but I got the notification.
A few minutes later, I got a call from our founder, emotional, telling me how massive this was for the company. That deal paid the largest commission check of my career.
And later, the champion on their side told me their internal campaign results were so strong that their team got huge bonuses too, the additional revenue they captured from implementing our solution even made a positive impact on their stock price. Win-win-win.
That’s how enterprise should feel.
The takeaways
Big deals rarely start big.
They start as:
- A lead
- A pilot
- A champion
- A tiny “yes”
Your job is to stay close, get creative, and keep moving the ball until the company gives you a reason to go big. And when they ask, “What would an unlimited license look like?” Pick up the phone. Because that’s the moment your whole year can change.
Good luck out there!
-Jesse