Dreamforce this year was an epic rebirth in many ways of AI for CRM, and a lot more than CRM. I’ll share more thoughts on that soon.
But being back there brought up a memory from a Dreamforce years ago that I think about more than almost anything else from those EchoSign days.
A Top 5 Customer With 2,000+ Reps on EchoSign for Salesforce
After Dreamforce 201X (I honestly don’t remember which year), we took one of our largest customers at the time, Groupon, out to a very nice dinner.
Groupon was a Top 5 customer for us. They had 2,000+ sales reps using EchoSign (now Adobe Sign) inside Salesforce. Every contract those reps sent went through us. For a startup our size, that was a big, important, strategic account, and we wanted them to know it.
So we did what vendors do after Dreamforce. We picked a fancy restaurant.
The Line Our Champion Said at the Table
Partway through dinner, our lead at Groupon turned to me and said:
“This is a pretty fancy dinner. That probably means I’m overpaying.”
It sounded like a joke. It wasn’t.
He was smiling, but he meant it. And it made me reflect, then and for years after.
He wasn’t being ungrateful. He was doing his job. He owned a vendor relationship with a real line item attached to it, and he was reading every signal he could get about whether that line item was fair. A very expensive dinner was a signal. To him it said: this vendor has margin to spare, and that margin is coming from me.
Customers Are Auditing Value All Year, Not Just at Renewal
A lot of us think about value at two moments: when the deal closes and when it renews. Customers don’t work that way. They are running a quiet, continuous audit of whether they are getting their money’s worth, and they update it with every interaction.
It doesn’t matter much what they pay in absolute terms. A customer paying $20,000 a year and a customer paying $2 million a year both want to feel they got a good deal. The big customer isn’t less sensitive because they have a bigger budget. They are often more sensitive, because someone above them is going to ask why the number is so high.
And they can always smell any sign they aren’t getting value.
The Signals Customers Read as “I’m Overpaying”
The fancy dinner is a mild one. The ones that actually cost you renewals and expansions are these:
- Mediocre support. If a customer paying serious money waits two days for an answer, or gets a canned response to a real problem, they do the math immediately. “We pay this much and this is what we get?”
- Upcharges that shouldn’t be there. Charging extra for SSO, for an API that should be standard, or for API access for an agent just to …. charge for it, or for an admin feature that makes the core product usable. Every one of these tells the customer the pricing was designed to extract, not to deliver. They notice, and they remember at renewal.
- A CS team that is only there to upsell. Customers can tell within one or two calls whether their CSM is there to make them successful or there to find expansion. If every QBR ends with a pitch, the customer stops taking the calls. Then you lose visibility right when you need it most.
- An AI agent that is too hard to train and/or deploy. This is the 2026 version of all of the above. If a customer buys your agent and then has to spend weeks of their own team’s time getting it to work, they are paying twice: once in dollars and again in hours. They feel that cost every single week, and it colors how they see the price tag.
None of these are pricing problems on paper. The price might be completely fair. But the customer doesn’t experience your price in isolation. They experience it next to everything else you do.
Why This Matters More in AI Than It Did in the Adobe Sign / EchoSign Days
With seat-based software, the value audit was fairly slow. You bought 2,000 seats, the reps used the product, and the question was mostly “are they using it?”
With AI agents and usage-based pricing, the audit gets much faster and much more granular. Customers can see what each task, each resolution, each outbound touch costs them. They compare it directly against what a human or a cheaper tool would cost. Every bad output, every retry, every time someone on their team has to clean up after the agent goes straight into the “am I overpaying?” column.
So the gap between “a fair price” and “feels like a fair price” matters even more now, and it shows up in renewal and expansion numbers much faster than it did with seats.
What We Changed After That Dinner
A few things got sharper for us after that night:
- We looked harder at whether our biggest customers were getting our best support, not just our best dinners. A fast, senior answer to a real problem is worth more to a Top 5 customer than any restaurant.
- We got more careful about add-on charges. If something felt like a tax on using the product the way it was meant to be used, it was a problem.
- We made sure the people talking to big customers were there to make them successful first. Expansion followed from that, not the other way around.
The dinner itself was fine. Customers like being taken care of. But a nice dinner can’t be the main way a customer feels valued. It has to be the least important way.
P.S. They Were Getting a Great Deal
For the record, Groupon was getting a great deal. 2,000+ reps, deeply integrated into Salesforce, at a price that was very fair for what they were getting.
But it didn’t matter what I knew. What mattered was what he felt sitting at that table. And for a moment, the dinner told him the opposite of the truth.
Every signal a customer sees should match the real deal they’re getting. That night, one of ours didn’t, and our biggest champion noticed.
