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ProService Hawaii is seeking an operational leader to own the workers' compensation captive P&L, drive financial performance, and shape claims strategy from within Hawaii's market.
You will lead the claims team, run end-to-end operations, implement daily huddles and scorecards, and advise clients and the executive team with data-driven insights.
Hybrid role based in Hawaii Kai with in-office and remote days; base compensation $135,000-$160,000 per year, commensurate with experience.
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.
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.
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.
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
The base compensation for this position is $135,000 - $160,000 per year, commensurate with experience and qualifications.
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.