Compliance and Regulatory Manager

At ProService, compliance isn’t a back-office function — it’s a core part of the value we deliver to over 3,000 Hawaii employers. Our clients trust us to keep them legally protected across licensing, insurance, governance, and government relations. This role is how that promise holds.

You’ll own the compliance function end-to-end — not manage pieces of it. Partnering closely with the Chief Counsel and Corporate Counsel, you’ll build regulator relationships, shape legislative strategy, drive first-to-market insurance products through approval, and keep every deadline across every function. The scope is broad, the stakes are real, and the authority is yours.

IN THIS ROLE YOU WILL

• Own all PEO state registrations, multi-state renewals, and ESAC filings — proactively closing compliance gaps before they become violations.
• Manage the full insurance compliance lifecycle: health carrier renewals, captive obligations, client reporting, and regulatory approvals for new product initiatives.
• Maintain corporate governance records, board minutes, and vendor/SaaS contracts; update client service agreements within 60 days of any regulatory change or product launch.
• Lead M&A due diligence, transaction drafting, and post-close integration to ensure licenses, contracts, and compliance obligations transfer cleanly.
• Build working relationships with DLIR, the Insurance Commissioner, and the Hawaii Retirement Savings Board; track legislation, develop advocacy strategies, and represent ProService at industry forums.
• Advise clients and prospects on regulatory developments, collaborate cross-functionally, and support development of first-to-market insurance products.

IS THIS ROLE RIGHT FOR YOU?

This role carries concurrent deadlines across licensing, insurance, governance, and litigation — all running at once, with no margin for gaps. You’ll have broad authority and real accountability in an environment where compliance failures have direct consequences for the clients who trust us.

This isn’t an execution role built on a pre-existing playbook. You’ll be expected to identify gaps and build the systems to close them. Each discipline in this role — multi-state licensing, insurance compliance, corporate governance, government relations — is complex enough to be a standalone career. You need to be strong across all of them.

WHAT YOU’LL BRING TO THE TEAM

We’re looking for someone with 3–5 years of experience in general/commercial litigation, employment law, multi-state compliance, or corporate transactional work. A JD is preferred; Hawaii Bar admission or eligibility is a plus. Prior PEO or HR experience, insurance law knowledge, and M&A background are meaningful advantages.

You’re probably a fit if:

• You have a track record of zero-defect filings across concurrent deadlines.You built the systems to make that possible — calendars, checklists, escalation protocols — and can point to a period where nothing slipped across multiple filing types.
• You exercise sound judgment under ambiguity.You know when to decide and when to escalate. You’ve navigated a regulatory gray area, made a defensible call, and documented your reasoning clearly.
• You can manage outside counsel and advise internal stakeholders simultaneously.You’ve coordinated legal strategy, kept leadership informed, and protected organizational interests — without letting any side wait.
• You track regulatory changes before anyone asks — and map implications before they become problems.You’ve surfaced a legislative or regulatory development proactively and brought a recommendation to leadership before it was on their radar.
• You’ve built trust with regulators and executives through consistency, not just credentials. A regulator or executive leaned on you because of your follow-through record — not just your title or background.

WORK LOCATION

Hawaii Kai, Oahu — Hybrid

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 | Remote: Monday & Friday

COMPENSATION

The base compensation for this position is $130,000 – $160,000 per year, commensurate with experience and qualifications.

At ProService, compensation is tied to performance. Strong results are recognized and rewarded, and there are clear paths to advance within the Legal & Compliance function and into senior leadership roles across the organization.

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.