Entrepreneur in Residence, AI Products

ProService 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. ProService 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.

WHAT YOU'LL DO

• Conduct structured customer discovery with ProService 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 ProService's existing commercial teams.

• Recruit and build the founding team for this business unit, working cross-functionally to leverage ProService'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.

IS THIS ROLE RIGHT FOR YOU?

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.

WHAT YOU'LL BRING TO THE TEAM

Prior experience building or scaling a product, business, or business unit is required — not because the path matters, but because the instincts that come from end-to-end ownership do. We are looking for someone who can hold commercial and technical thinking at the same time, get in front of customers without hesitation, and build something real in an environment that isn't fully formed yet.

• 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.i

• 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.

WORK LOCATION

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.

COMPENSATION

The base compensation for this position is $135,000.00 to $160,000.00 per year, depending on experience and qualifications,with equity included as part of the total package.

WHY YOU'LL LOVE PROSERVICE

ProService is a Hawaii-based PEO combining payroll, HR, and benefits expertise with purpose-built technology — all backed by the best local service in the islands.

Backed by Silver Lake and recognized as one of Hawai?i’s Best Places to Work for 20 consecutive years, we’re a team of high performers united by one mission: Empowering Employers to Succeed in Hawai?i.

• A PROhana unlike any other. We assume the best in each other, give feedback focused on what’s right—not who’s right—and show up every day. This isn’t just a workplace. It’s a community.

• Do work that matters. You’ll see exactly how your contributions move the needle—meaningful problems, real decisions, and a seat at the table.

• Grow without a ceiling. Internal roles post first, and we reimburse certifications, conferences, and memberships. Your growth is our growth.

• Compete, collaborate, and win together. High expectations, real accountability, and a team of experts ready to help you push through any obstacle.

• Total rewards built around your whole life. Fully paid healthcare, 401(k) matching, paid parental leave, student loan assistance, employee assistance programs, and paid time off—just to name a few.