I'm hiring a few people who are the best at what they do.

I'm Tucker Bern, the founder of Caddy. This page is long on purpose. If you're good at what you do, you'll read all of it, because you want to know exactly what you'd be walking into before you spend a minute on an application.

Here's who I'm looking for. You're the person your last company leaned on when something had to get done. You don't need to be managed. You're competitive, you keep score, and you'd rather be judged on what you got done than on the hours you were online. You already use AI every day, and it bugs you to watch a team do by hand what a system could do for them.

If that isn't you, honestly, please don't apply. We're a small team and we hire slowly. One wrong hire costs us more than an empty seat, and it costs you a year you could have spent somewhere that fit.

Where I come from

My family built a business over 25 years and sold it, with 1,200 employees at exit. I was inside that whole process: getting the company ready to sell, the diligence, the deal itself. It taught me what a buyer pays a premium for, what they mark down, and how much of a company's value sits in the way the work gets done.

Today I run a family office focused on private investments. Our holdings span underground utility locating, manufacturing, drones, healthcare, auto and car washes. When AI started moving faster than any team could keep up with, I didn't wait for a vendor to figure it out for us. I learned the tools, then audited my own companies, and found leaks everywhere.

One of them: a single person checks two and a half million utility lines a year by hand, sixty and seventy hour weeks of it. That's one process in one company. That is why Caddy exists.

What Caddy does, and why now

Caddy is an AI deployment company based in Dallas, Texas. We work with operations heavy businesses. A fractional AI Chief Executive from our team goes into the business, finds the work eating the team's week, builds the AI systems that do it, and trains the people to run them. The client owns all of it: the plan, the system and the data.

The work is concrete. Material ordering by phone for an electrical contractor. Invoice drafts built from a roofer's job close-outs. Daily reports that field crews speak in English or Spanish. We've audited or scoped twenty-two businesses so far, from owner-run shops to operations doing about a hundred million a year. You can see them in our results.

Why now: almost every owner I talk to knows AI matters and has no idea where to start. The tools can now do real work inside a business, not just answer questions in a browser tab. Somebody is going to put these systems into every operations heavy business in the country. I want that to be us, and I want it done right.

The three roles

We're hiring for sales, customer success and engineering. If you're great at something else and you read this far, tell us anyway.

How we work

You'd work closely with me, with Joshua Armant, our co-founder and CRO, who has 12 years at Microsoft working with Fortune 500 companies and the federal government, and with Peyton Thompson, our solution architect, who spent five years at Accenture. More on all three on our About page. Here's what we hold each other to.

• Client outcomes are the product. We are paid to change how a business runs. Everything we build is judged by that.
• Leverage over hours. We do not reward busy. We reward the system that makes ten hours of work disappear.
• Honest dealings. With clients, with each other, and with the numbers. Bad news travels fast here, and it is never punished.
• Real ownership. You will own work end to end and be trusted with it. That also means you own the result.
• High standards, small team. Expect to work closely with the founders and to be held to the same bar they hold themselves to.
• Written first. Plans, decisions and handoffs are written down, so anyone can pick up the work and nobody repeats a mistake.
• AI in every workflow. We run our own company on the same kind of systems we build for clients.
• Short loops. We check work against the real world early and often, and we would rather change course on Tuesday than defend a plan on Friday.
• Say it, then do it. Commitments are specific: who, what and by when. Then they get done.

Our hiring steps

1. Apply below. One short form. Send a link to your resume, LinkedIn or portfolio, and tell us about something you built or ran.
2. We read every application. If there is a fit, we reach out to set up a first conversation.
3. First conversation. We talk about your work, what you are looking for, and how we work, so both sides know what they would be signing up for.
4. A practical exercise. A short piece of work drawn from the kind of problems we solve, so you can show how you think instead of telling us.
5. Meet the team, then a decision. You meet the people you would work with. We make a decision and tell you plainly either way.

If this is you

If you read this far and kept nodding, apply below. Skip the cover letter. Tell me about something you built or ran, and what changed because of it. I read every application myself.