By Richard Ryffel, Executive Director of Business Leadership & Professor of Practice at Purdue University
One of the most enduring truths in venture is this: great companies are built in partnership with their customers, not in isolation from them. And nowhere is this more evident than in early-stage sales. It’s tempting for founders to do most of the talking — especially when they’re passionate about their product — but it’s listening that wins deals.
As Jerry Seinfeld once noted, “people don’t want to hear the story, they want to tell you theirs.” And that holds true in enterprise sales too. If your buyer is a Seinfeld-style low-talker, lean in. If they’re a high-volume skeptic, lean in harder.
SixThirty has worked with hundreds of founders scaling enterprise sales at the intersection of money, health, and privacy. Across those experiences, one pattern holds: the founders who excel in sales embed the voice of the customer into their sales motion — early and often.
Listen Like It Matters (Because It Does)
Empathetic selling is a skill, not a personality trait. It’s not about charisma or monologues, it’s about curiosity and humility. The best founders ask powerful, open-ended questions and tune into WIFM (what’s in it for me), the customer’s internal radio station.
Every prospect call is an opportunity for the customer to hand you a roadmap to the sale if you’re quiet long enough to hear it.
And in case you’re wondering, no, it doesn’t require a plaid jacket or the gift of gab. As George Costanza once proved, sometimes the best approach is to do the opposite of your instincts — especially if your instinct is to pitch too much, too fast.
Focus on the Problem, Not the Product
The job of a founder on a sales call is not to explain every feature your product can perform. It’s to clearly state what problem you solve, and why that problem matters today. Too often we see entrepreneurs “show up and throw up,” delivering a firehose of features before clarifying what the customer actually needs.
Harvard’s Ted Levitt said it best: “People don’t want a quarter-inch drill. They want a quarter-inch hole.” Founders must stop selling drills and start selling holes.
Features Don’t Sell. Benefits Do.
Every startup team should be fluent in the Feature–Function–Benefit framework. If you can’t explain what something is, what it does, and how it helps the customer, then you’re not ready to sell it.
Customers — and investors — don’t buy features. They buy outcomes. When done well, this kind of value articulation sounds effortless. Think of it like Kramer selling the sizzle, not the steak… or latex, not just the job title.
Three Things Founders Can Do Today
To embed the voice of the customer more effectively, start here:
- Rewrite Your Pitch Around the Customer’s Problem.
Strip your deck down to three slides: (1) the problem, (2) how your solution uniquely solves it, and (3) the value created. Be rigorous. If the first slide doesn’t make your prospect nod, the next two won’t land either. - Build a Voice-of-Customer Feedback Loop.
After every sales call, document what you learned: buyer pain points, language they used, objections raised, success metrics cited. Review weekly with your team. That’s how product-market fit gets built, one conversation at a time. - Practice With People Who Know the Room.
Role-play sales calls with trusted advisors. Get feedback on how clearly you’re tying benefits to outcomes. If your pitch sounds like “Seinfeld’s stand-up about nothing,” tighten it. The customer’s time, and trust, is precious.
So the next time someone says, “Sell me this pen,” don’t talk about the ink. Ask them what they’re trying to write. And if you do that well, just maybe, you’ll become the top latex salesperson at Vandaley Industries.
