Entrepreneur in Residence, AI Products

Pro Service is looking for a builder — someone who can take a validated problem space and turn it into a revenue-generating AI business. This isn't a role for a strategist who hands off to an execution team. You'll own the full arc: customer discovery, business model design, product delivery, go‑to‑market, and team building. You'll operate with the autonomy, resources, and financial upside of a founder — inside a company that's already built deep trust with Hawaii's business community.

The problem space is defined: there's a meaningful opportunity to bring data, reporting, and AI services to Hawaii's SMBs — businesses that have historically been underserved by enterprise-grade tools. Pro Service has the client relationships, the distribution, and the credibility to make this real. What we need is someone who can move fast, validate what actually resonates, build the delivery engine, and get to revenue — all while learning the market and the organization at the same time.

• Conduct structured customer discovery with Pro Service clients to validate willingness to pay, identify priority use cases, and refine the offering scope and packaging.
• Build the business case — including pricing model, unit economics, and proforma financials — and secure internal alignment and resource commitment for launch.
• Determine and execute the optimal build/buy/partner strategy to deliver the offering at quality and scale, establishing operational infrastructure, SLAs, and support structures.
• Lead end-to-end go-to-market execution from alpha through full commercial launch, developing sales motion, marketing positioning, and customer success approach in partnership with Pro Service's existing commercial teams.
• Recruit and build the founding team for this business unit, working cross-functionally to leverage Pro Service's existing infrastructure while standing up what's new.
• Drive toward clear milestones: first revenue within 4 months, GA launch within 6 months, and a defined ARR target by end of month 12.

This is an operator‑founder role where speed and accountability are non‑negotiable. You'll be building in a market you may not know yet, inside a company you'll need to learn quickly, while simultaneously running customer discovery, making product decisions, and driving toward revenue. The scope is real — you own this from concept to scale — and so is the ambiguity. There's no established playbook to follow, and the early months will require you to earn trust with our clients and internal teams while moving fast.

Worth knowing: this role requires you to be based in Hawaii, and connections to the local business community are a genuine advantage — not just a nice‑to‑have. Success looks like someone who sets their own direction, course‑corrects quickly when the data says something different, and doesn't need a support system to operate.

• You've built something from scratch — a product, a business unit, a revenue stream — and you can point to what you learned when it didn't go as planned. You ran customer discovery on a product assumption, found out you were wrong, and pivoted the offering before writing a line of code.
• You're comfortable being the person who figures it out — not the person who delegates the figuring. When faced with an unfamiliar technical or operational problem, you prototype a solution yourself before deciding whether to hire, buy, or partner your way through it.
• You lead with the customer. You validate before you build, and you measure what matters — not what's easy to measure. You've excelled in a feature or product direction because the customer data didn't support it, even when internal stakeholders were pushing to ship.
• You know how to move inside organizations — building trust across teams without slowing down to get sign‑off on everything. You've driven cross-functional alignment on a go-to-market launch without formal authority over the teams involved.
• Your technical fluency is real enough to earn credibility with sophisticated clients and make sound product decisions, even if you're not primarily an engineer. You can prototype a working demo or proof of concept independently — and you've used that to get early client buy-in before a full build was ready.

This role is based out of our Hawaii Kai office. We offer a flexible hybrid schedule that gives you the structure of in‑person collaboration with the flexibility of remote work. In‑office Tuesday–Thursday, with remote flexibility on Mondays and Fridays.

The base compensation for this position is $ to $ per year, depending on experience and qualifications, with equity included as part of the total package.

• Fully paid healthcare, 401(k) matching, paid parental leave, student loan assistance, employee assistance programs, and paid time off—just to name a few.