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John Long has spent 15 years selling technology — and the clearest pattern he’s noticed is that when product and sales stop trusting each other, the company doesn’t just slow down, it inverts.
“Developing product is a little bit like playing Battleship,” John Long tells me. “We do our best to get close. But we’re lobbing things over and hoping that we hit something.”
He says it without drama, the way you describe a thing you’ve made peace with. And it would be a perfectly ordinary metaphor — every product person has felt the fog of guessing what a customer actually wants — except that Long doesn’t stop at the guessing. He stops at what happens after the miss. Because the miss, in his telling, is where the trust starts to die.
Long has spent 15 years selling technology, and he’s a particular kind of seller. The kind who digs into the product until he barely needs a sales engineer, who can demo the thing himself because he’s bothered to learn how it actually works. That’s rarer than it sounds. “Some organizations don’t even allow that,” he says — they keep sellers out of the product entirely. He’s spent his career on the other side of that wall, close enough to product to watch the relationship between the two functions either compound or collapse. Now he’s the CEO of Thynk AI, a company building AI agents that handle the parts of selling no one enjoys. But the thing he keeps returning to isn’t the technology. It’s the human seam between the people who build and the people who sell, and how easily it tears.
Start with what it looks like when the seam holds, because Long has lived that too. He describes it almost wistfully. “If you have sales in one silo and product in another silo and the two never meet, product market fit is going to be a disaster.” The inverse — sales and product cross-pollinating — is the only way he’s seen a company nail it. He puts it bluntly: “If the guys developing don’t know what the guys using are actually doing with the tools, it’s not gonna work.” When that gap stays open, the seller is left doing something absurd. “You’re trying to sell ice cubes to Eskimos.” The product does A, B, and C. The customer needs X, Y, and Z. And so, Long says, “I spend 90% of the sales process trying to convince them that A, B and C is actually what they want to buy.” His favorite saying cuts the other way, toward the thing the silos make impossible: “Sell the customer what they want to buy.”
But the slow rot doesn’t announce itself as a strategy failure. It announces itself as friction, and the friction has a sound. Long can reproduce it from memory. The sales leadership preaching down at the reps: “Sell what’s on the truck. Don’t make up things. Don’t sell vaporware. Don’t sell things that don’t exist.” The sales leader carrying complaints up to the product leader: we need the product to do these things, and it’s not doing them. And the product leader, if he’s lost touch with what the customer actually needs, firing back the line that tells you the trust is already gone. “Hey, no, we gave you the perfect product. Quit complaining and go and sell what we’ve built.”
I ask him what the early symptoms are, the things you’d notice before anyone names the problem. He doesn’t reach for a framework. He reaches for the implementation team — the people downstream of every overpromise, the ones who inherit the gap between what was sold and what exists. He voices them, and you can hear that he’s heard this exact lament more than once. “Ah, I wish the sales reps would actually represent the product accurately. I’m having to fix all of their problems. I’ve got customers that are frustrated from day one.” Overpromising, churn, a backlog of broken implementations — these are the visible signs. Underneath them is the invisible one: “this spiral downward of friction, frustration.”
Then we get to Battleship, and the metaphor turns out to be sharper than it first appeared. Because the problem isn’t that people miss. Everyone misses. The problem is what each side is allowed to conclude from a miss.
Watch what happens, Long says, when a sales rep brings real intelligence back from the field — the customer needs it to do these things — and the product team builds toward it and lands close but wrong. “We splashed the ship, but we didn’t hit the ship.” A reasonable outcome. A near miss in a game that is mostly near misses. But the conclusion the product team draws is not reasonable. “The product team inherently says, ‘Oh, the sales rep doesn’t know what he’s talking about. He doesn’t know how to gather requirements. I don’t trust him. I’m not gonna listen to him anymore. I’m doing this on my own.’”
One miss, and the channel closes.
Now run the same miss the other direction. The product team, working from its own instincts, builds something and it doesn’t land. Same result, same splash, same near miss. But the verdict flips entirely. “If the product team develops something and they miss the ship, then they’re like, ‘Well, it’s okay. We got closer.’” The miss becomes a milestone. Foundational. A step in the right direction. “Suddenly it’s okay.”
That asymmetry is the whole thing. The sales rep’s miss is evidence he can’t be trusted. The product team’s miss is evidence they’re learning. Same game, same odds, two completely different scorecards — and the scorecard is what determines whether anyone keeps listening to anyone. Long isn’t bitter about it; if anything, he’s generous to both sides. “We all miss,” he says, twice, like he wants to make sure it lands for each camp. And then the line that defuses the blame entirely: “I genuinely don’t think anyone ever sets out to be like, ‘I’m gonna build a product that really doesn’t do anything.’”
He’s quick to point out the miss isn’t even fully anyone’s fault, because the target keeps moving. “There’s generally a lot of cooks in the kitchen on the customer side.” He acts out the contradiction the product team is asked to satisfy: one customer insists the button belongs in the upper left corner, because that’s where everybody looks. The next person in the same company is just as certain it belongs in the bottom left, for the same reason. “You’re never gonna get it exactly right.” The honest goal isn’t precision. It’s persistence. “Hopefully we’re hitting boats every once in a while. And then we’ve got something solid and we can start to kinda hit around that.” Like Battleship, he says, you eventually sink the ship — but only if both players are still willing to call out coordinates.
Which is why the cure he describes isn’t a process. It’s a relationship. And he has a specific one in mind.
“Inherent in that type of relationship is a foundation of trust,” he says, and then he gets concrete in a way that turns the abstraction into a person. His business partner today — at the AI company he’s building right now — is the same man who ran product at a company where Long was selling 15 years ago. The product guy. The one developing while Long was out selling what got developed. I ask, and the number he gives me lands hard enough that I say “wow” out loud. The two of them have traveled together, he estimates, “well over 100 times.”
Not for offsites. For customers. “We were constantly connected at the hip. I was selling, he was developing, and we had this deep level of trust with each other.” For seven or eight years, multiple times a month, they got on planes together — the seller and the builder, going to see the same customers with the same eyes. “We were cross-pollinating our two worlds on a regular basis every single week. Either I was in with the product team or he was with me on sales calls, one or the other.”
That’s the antidote to the Battleship asymmetry, and notice what it actually requires. It’s not better requirements documents. It’s proximity sustained long enough that neither side can hide behind the wall. When the product guy is sitting in the customer meeting, he doesn’t get to dismiss the sales rep’s intelligence as secondhand — he heard it himself. When the seller is sitting in the product room, he doesn’t get to treat a miss as betrayal — he watched how the sausage got made. The trust Long describes isn’t a feeling they decided to have. It’s a residue, the thing left behind by a hundred shared flights.
What strikes me, listening to him, is that the trust came first and the results followed, not the other way around. Long has had the dialed-in experiences every seller dreams about — the products so well-fit that customers wanted a quote before he finished the pitch, the runs of growth where the scaling never scaled complexity. But when he traces those back, they don’t start with a great product. They start with a seller and a builder who refused to operate in separate rooms.
The spiral he describes — the one that starts with a single near miss and ends with two functions that have stopped speaking — is the default. It’s what happens when you let the wall stand and let each side keep its own scorecard. The companies that escape it don’t escape because they miss less. They escape because someone decided that a miss was a coordinate, not a verdict, and kept playing.
Near the end, Long is describing the AI company he’s building, and he mentions, almost in passing, that his co-founder is that same product guy. The one from the first story. The one he’s flown with more than a hundred times. They scrapped one plan, elevated another, and ended up here — still the seller and the builder, still connected at the hip, fifteen years and one industry later.
He doesn’t frame it as proof of anything. But it is. The whole conversation has been about what happens when sales stops trusting product, and the answer has been sitting in front of me the entire time, in the shape of a man who never let it happen.
Guest Bio: John Long
John Long is the CEO and Co-Founder of Thynk AI, a Utah-based company building AI communication agents that handle the full pre-sales motion — cold outreach, lead qualification, scheduling, and beyond — without a human ever touching the conversation. Rising to prominence in enterprise technology sales over a 15-year career, Long built his reputation not as a manager of sales teams but as the kind of operator who embeds so deeply with product that the line between salesperson and builder disappears entirely. He was once the lone sales representative tasked with opening a brand-new market segment, and over the course of more than 100 trips with his product team, he helped construct what became a multimillion-dollar recurring revenue line from scratch. The product partner he worked alongside on that run is now his co-founder at Thynk AI.
Founded in mid-2024, Thynk AI entered the market with a thesis that most AI SDR tools are window dressing — capable of sending a templated email but unable to hold a real conversation, respond to replies, or carry a prospect from cold contact through to a qualified meeting without human intervention. Long and his co-founder built Eric, Thynk AI’s AI sales agent, to close that gap end-to-end. Eric makes and receives calls, sends texts and emails, conducts live phone meetings, qualifies and disqualifies prospects, and books follow-ups autonomously. The company’s own website reflects the conviction: there is no human contact available until Eric has qualified you. In its first 90 days of operation, the platform generated $13,440,000 in pipeline for its users with no human SDRs and no ad spend.
Long sees AI communication agents as a platform, not a point solution. Thynk AI has already extended Eric beyond outbound sales into customer service, HR, and accounting functions — any workflow where a business currently deploys a human to conduct a structured, repeatable conversation. The company operates from Lehi, Utah, and Long continues to serve as an advisor and speaker on practical AI deployment for growth-stage companies.
Hey,
Thanks for reading this. I mean that. There's a lot of content out there competing for your attention, and you spent some of it here. I hope it was worth it. Even better, I hope it prompted you to think about something differently enough that you'd share it with someone who'd get something out of it too.
I started this podcast because tactics never stuck with me. What stuck were stories — business biographies, autobiographies, the decisions people made and why they made them. The principle only clicks once you know the story behind it.
So I built the thing I wanted to read. Every week I have two conversations with people who build in technology and product. Then I write the essay I wish I could find — one that puts you inside the conversation, through my eyes. What caught me off guard. What I kept thinking about after we hung up. Where the principle actually lives once you strip away the jargon.
I make this for myself first. If you read the way I do, you’ll want it too.
PS — If you want to pitch coming on the show, or you know someone I should talk to, shoot me an email at caden@hey.com with "January752" in the subject line so it gets past my filters. I'm not optimizing for famous guests. I'm optimizing for interesting conversations, even from people who aren't LinkedIn influencers.
