Workers' Compensation Manager / Claims Counsel

At ProService, we’ve been helping Hawaii employers navigate the complexity of running a business for 30 years — and workers’ compensation is one of the most consequential areas we touch. We run our own workers' comp captive, which means we own the risk, the strategy, and the financial results end to end. That structure is a real competitive advantage for the businesses we serve, and it's why this role carries weight.

This is a full-ownership leadership role with real P&L responsibility. You’ll lead the claims team and run the captive program - build the operational systems that drive performance, shape claims strategy, and serve as a trusted advisor to clients navigating one of the most complex areas of employment law in Hawaii. You'll have the authority of someone running their own business inside ours, and the accountability that comes with it. Success means a healthier loss ratio, stronger client outcomes, and a program that performs better every quarter because of how you lead it.

IN THIS ROLE YOU WILL

• Own the P&L for the workers' compensation captive — managing loss ratios, reserves, and program profitability while making the strategic calls that drive financial performance.
• Lead end-to-end claims operations — owning closure rates, average claim costs, time-to-resolution, and client outcomes across the full program.
• Run a disciplined operating rhythm — daily huddles, weekly scorecard reviews, and monthly 1:1s — so every team member knows exactly how they're performing against goals.
• Coach and develop claims professionals through structured feedback, timely performance conversations, and targeted development plans — addressing underperformance directly while investing in top performers.
• Leverage AI and data reporting tools to surface loss trends early, streamline claims workflows, and build data-informed strategies that improve results across the captive.
• Advise clients and the Executive team with authority — delivering monthly claims reports for key accounts, weekly performance updates to leadership, and clear-eyed guidance on Hawaii's workers' comp landscape.

IS THIS ROLE RIGHT FOR YOU?

This is an operational leadership role where accountability and follow-through aren’t optional —it's the mandate. You’ll be responsible for real outcomes: closure rates, average claim costs, time-to-resolution, and client satisfaction. When results aren’t where they need to be, you’re expected to move quickly. The work is both internally team leadership focused and client-facing relationship management, so you’ll need to be effective on both sides of that line.

Worth knowing: this role requires working knowledge of Hawaii's workers' compensation system and a solid grasp of captive or insurance economics — or a demonstrated ability to get there fast. You'll be expected to advise independently on claims strategy, captive performance, and client escalations within your first 90 days. You won't be doing it alone — you'll have executive support, data tools, and a capable team behind you — but this is best suited for someone who's comfortable leading through ambiguity and holding the pen on financial outcomes.

WHAT YOU’LL BRING TO THE TEAM

We're looking for a leader who blends legal or claims expertise with real financial and operational instincts. Attorney-level training or equivalent experience with workers' compensation systems is strongly preferred, and comfort with P&L ownership or captive/insurance economics will set you apart. Relevant Hawaii WC experience is a plus, but a strong learner with leadership fundamentals and a track record of ownership can get up to speed quickly. A JD is preferred; Hawaii Bar admission or eligibility is a plus.

You’re probably a fit if:

• You think like an owner, not just a manager. You've been handed a budget or a P&L and made it healthier — cutting loss, tightening spend, or growing margin — and the business felt the difference.
• You run structured operating rhythms and actually use them. You've held consistent 1:1s, scorecard reviews, and performance check-ins, and your team hit its numbers because of them — which meant clients got faster, cleaner resolutions.
• You coach people at every performance level. You've had the hard conversation with an underperformer and invested in a high-potential teammate, and can point to how both changed the experience clients had with your team.
• You stay steady in high-stakes client situations. You've walked into an escalation that needed both clear communication and sound judgment, and the client left more confident than when it started.
• You turn data into decisions. You've spotted a loss trend or workflow gap in the numbers, designed the fix, and seen it through — so the next claimant had a better, faster outcome.

WORK LOCATION

Hawaii Kai, Oahu — Hybrid

This role is based out of our Hawaii Kai office. We offer a hybrid schedule that gives you the structure of in-person collaboration with the flexibility of remote work.

In office: Tuesday – Thursday | Option for remote: Monday & Friday

COMPENSATION

The base compensation for this position is $135,000 – $160,000 per year, commensurate with experience and qualifications.

WHY 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 Hawaii’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 Hawaii.

• 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.