Cowboy, Confrontation, and $100M: How Tennr Hires for Extreme Ownership

Why Work Here is a series in which Amit Matani, CEO of Wellfound, has honest, behind-the-scenes conversations with founders, executives, and employees about why their companies are worth joining.

Most companies default to the same culture values: customer obsession, innovation, integrity. Tennr’s CEO Trey Holterman thinks that’s corny. His company’s values are Cowboy and Confrontation—and if that makes you uncomfortable, that’s the point.

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“Everybody’s customer obsessed. We think that’s a little corny. So we chose problem obsessed because we want to solve the damn problem. And if a customer is getting in the way, we’re going to make some noise.”

It’s an unusual stance for a company that just raised $100 million and is reshaping how patients move through the healthcare system. But these values help explain how three engineers straight out of college built a company now processing referrals for more than 20% of Americans annually.

The Problem That Started With Mockery

Tennr began with a challenge from Holterman’s mom, a family medicine doctor. She made fun of the research project he and co-founder Diego were working on and pushed them toward something real.

“She was making fun of whatever stupid research project we wanted to work on and said, ‘Why don’t you go solve something actually interesting? Go figure out why this imaging center never gets back to me.’”

That simple question revealed a massive structural failure. When doctors refer patients to specialists or therapies, providers must compile documentation proving patients qualify. It’s often 70+ pages of chart history interpreted against shifting payer guidelines.

Holterman explains it this way:

“It’s almost like putting together a court case. Providers in the U.S. have the burden of proof to justify why a patient needs a treatment.”

The outcome is predictable: conversion rates around 54%, denial rates around 34%, and patients lost in the gaps.

Tennr built a platform that handles everything from patient contact to prior authorizations to cost transparency. They’ve boosted conversion rates to 71% and cut denials by roughly 45%. When you deliver those numbers, Holterman says, the product spreads through word of mouth.

Three Engineers Who Solved an Obvious Problem

Holterman doesn’t over-romanticize the origin story. They just solved something that was painfully obvious.

Despite building RaeLM™, a vision-language model trained to interpret unstructured medical records against payer criteria, they don’t lead with AI.

“If you go on our website, you won’t see AI anywhere. We’ve just been laser focused on solving the problem.”

The clarity of that focus shows up in the results:

“Provider B converts patients at 54%. We come in and get that to about 71%. We drop denials on average 40 to 50%. And we lower their operating cost.”

Many founders talk about early-stage nostalgia—those first few scrappy years. Holterman doesn’t buy it.

“It’s so much more fun now. We have a bigger, better, badder team actually solving the problem.”

The Cowboy Who Flew With Pizza

Holterman traces Cowboy back to his mom’s family in central California:

“My mom’s family is from central California, kind of weird cowboy types. Their flow toward life is extreme self-reliance and extreme ownership. If something breaks—saddle gets torn—you’re fixing it yourself. You take matters into your own hands.”

That mindset is what he wants inside Tennr:

“We don’t want a bunch of Walter Cronkites. We don’t want people reporting the news. Be loud about what’s going wrong, but come with a solution or the right people.”

Each Friday, Tennr recognizes employees who demonstrate the values—and Cowboy wins most often.

The standout story: A customer success manager heard a client mention in passing they’d never tried New York pizza. She scheduled an onsite for the following week and boarded a plane with a Joe’s Pizza pie.

“They joked about wanting New York pizza. She said, ‘Let’s do an onsite next week,’ and showed up with a pizza she’d flown with. There are hilarious photos of her carrying it on the airplane.”

Holterman repeats a key point:

“I can’t make somebody like that. All you can do is find those people, get them in, give them running room, and protect them from the curmudgeons who want to ruin that. Maybe one of the most important things is keeping the other types of people out. It’s like a garden.”

Confrontation as an Anti-Value

Confrontation was deliberately chosen as a counterweight to politeness.

“Most people you hire are nice, and nice people index away from confronting reality. Everything about this company has been hard. If you don’t have people seeing reality undisturbed, you run into problems.”

But as companies grow, people become more hesitant to challenge the CEO. Holterman disarms that dynamic by making himself the lowest-stakes target in the room.

“I’ll say, ‘I have no clue what I’m talking about here.’ And that happens a lot.”

He’ll also throw out outrageous ideas to lower the bar for everyone else:

“I’ll say something insane, like picking up prospects in a helicopter and landing them near Alinea. And then someone will say, ‘No, Trey, this is all clinicians—we’ll never make that much money.’ Then I can say, ‘Okay, I had no clue. What are the ideas?’”

Once he’s said something absurd, it becomes much easier for others to speak freely.

Room to Run

Holterman often uses a specific analogy when describing the kind of people Tennr hires:

“You ever seen videos of dogs that walk themselves, holding their own leash? I always tell people, there’s no leash. I don’t have a leash.”

He wants people who run on their own energy—not people waiting to be managed.

This mindset has positioned Tennr at an inflection point:

“Things that used to take years to roll out, like a co-pay assistance program, we’re rolling out in software with an update. Every patient going in for this type of procedure now has every possible co-pay assistance program at their fingertips.”

If you want autonomy, ownership, and the chance to fix a broken part of the healthcare system, Tennr is built for that. If you’re good, they’ll give you space to run.

Final Tips for Founders, Recruiters, and Job Seekers

Founders

If your values sound like everyone else’s, they mean nothing. Values that some people dislike are often more useful than values everyone ignores.

Recruiters

Tell real stories—pizza flights, bold problem-solving, honest pushback. Specific examples help candidates self-select.

Job Seekers

If a company can’t tell you who wouldn’t thrive there, be cautious. Strong cultures are defined by clear trade-offs, not universal appeal.