AI Systems Weirdo
# We are looking for a needle in a haystack, perhaps slightly crazy, likely a weirdo.
We are not looking for ordinary. We are looking for extraordinarily exceptional and visionary with tremendous technological capabilities. If you do not hear from us within 24 hours, we are not interested.
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## The role
UniteGPS makes Crosswalk K12. We do GPS tracking, route optimization, and student ridership for school districts across the country. We are a small, profitable, bootstrapped team that has been outrunning competitors many times our size for over a decade.
We want to do it again, with leverage that did not exist a year ago.
We want to become an AI-native company. Not "we use ChatGPT sometimes" AI-native. Actually AI-native. A continuous, self-improving fabric layered over every process we run. Sales, customer success, route optimization delivery, hardware logistics, billing, accounting, support, development. Every process. Listening, reading, watching, drafting, checking, suggesting, automating, learning. Every day better than the day before.
We need one person to own this. To sit in our office in South Portland, Maine. To watch how we work, decompose every process, design the AI layer that magnifies each person on the team into five or ten of themselves.
You are not replacing anyone. You are making this team dangerous to our competitors.
This is not a Head of AI role. This is a builder role. You report to the CEO. You decide the stack. You stand up the models. You write the code. You write the prompts. You write the evals. You design the harnesses that let agents iterate on a problem until the solution is beautiful. You ship, you measure, you test, you tear down what is not working, you build it again better.
In-person, South Portland, Maine. Non-negotiable. Role begins in July.
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## The questions we want answered
Answer these in writing. No resume. No cover letter. No AI-assisted prose, we will know. Take the time it takes.
**1. The flywheel.** Describe in detail your vision for turning a small operating company into an AI-native flywheel. What does the flywheel actually look like? What goes in, what comes out, what compounds, and why does it accelerate over time rather than plateau? Be specific. Draw the picture in words.
**2. The first 90 days.** You are sitting in our office on day one. What do you do in the first week? The first month? By the end of 90 days, what is running in production, what have you measured, and what does the team say about the change?
**3. The process you can already see.** Pick any process you can infer from this posting and from our public-facing materials. Sales, customer success, route optimization delivery, hardware logistics, anything. Decompose it. Show us where humans add irreplaceable judgment, where they are doing toil, and where they are the bottleneck. Then sketch the AI layer you would put over it. What gets fully automated, what gets a copilot, what gets a checker, what gets left alone, and why.
**4. Magnification, not replacement.** What does it actually mean to magnify a teammate 10x with AI? Pick one role at any company you have worked at, and describe concretely what their day looks like before and after. What stays the same? What changes? How do they feel about it?
**5. Show us the work.** Send three things you have built that you are proud of. Things you built because you wanted to, not because you were paid to. Links, screenshots, write-ups, whatever. For each, tell us what it does, why you built it, and what you learned that you did not expect.
**6. Show us how you actually work.** Your AI setup. Dotfiles, CLAUDE.md, AGENTS.md, custom MCP servers, scheduled agents, n8n workflows, Raycast extensions, shell aliases, Obsidian, whatever you actually use day to day. We want to see the layer you have already built around yourself.
**7. The thing nobody asked for.** Pretend you have been here for six months. You have read every email, listened to every call, sat in on every internal chat. Describe one specific thing you would have built by now that nobody asked for, and that would have made the company measurably better. Be specific. What does it do, what does it watch, what does it produce, who does it talk to, and how do you know it is working?
**8. The strong opinion.** What is something you believe about building AI-native companies that most people you respect would disagree with? Defend it.
**9. The belief you updated.** What did you believe strongly about software, AI, or business two years ago that you now think was wrong? What changed your mind?
**10. Why us, why Maine, why now.** Be honest. Vague answers are the wrong answers.
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## How to apply
Email your answers to christopher.bunnell@unitegps.com. One PDF, one document, whatever. We do not care about format. We care about substance.
If we want to talk, you will hear from us within 24 hours of receiving your packet.
If you do not hear from us within 24 hours, we are not interested. Do not follow up.
A few rules to protect everyone's time:
- Apply only through the email address above. If you reach out to me directly through any other channel, you will automatically not be considered.
- Do not message me on LinkedIn. If you do, you will be blocked.
- Do not "circle back," "bump this," or send a follow-up. The 24-hour rule is the rule.
If you cannot follow these three instructions, you are not the person we are looking for and we are saving us both time.
Christopher Bunnell, CEO, UniteGPS