Compliance and Regulatory Manager

ProService is looking for a Compliance & Regulatory Manager to own our compliance function end-to-end - not manage pieces of it. You’ll be the primary steward of regulatory integrity across multi-state PEO licensing, insurance compliance, corporate governance, and government relations. The bar is high and the stakes are real: hundreds of Hawaii employers trust ProService to keep them legally protected, and you’re the person who ensures that promise holds.

You’ll partner closely with the Chief Counsel and Corporate Counsel, but you own the execution. That means building regulator relationships, shaping legislative strategy, and driving first-to-market insurance products through approval - all while keeping every deadline across every function.

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.
  
  

What You’ll Bring To The Team

We don’t measure candidates by resume alone. We’re looking for people who hold themselves to a standard most don’t, who take feedback as fuel, and who are wired to own their results.

• 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 (health, workers’ comp, 401(k)), and M&A background are meaningful advantages.
• A track record of zero-defect filings across concurrent deadlines - because you built the systems to make that possible.
• Sound judgment under ambiguity: you know when to decide and when to escalate.
• The ability to manage outside counsel, advise internal stakeholders, and protect organizational interests - all at once.
• A habit of tracking regulatory changes before anyone asks - and mapping implications before they become problems.
• Trust built with regulators and executives through consistency and follow-through, not just credentials.
  
  

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. Worth knowing: 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.

WORK LOCATION

We welcome applications from candidates based in Hawaii, who would work a hybrid schedule (in-office Tuesday–Thursday, option for remote Monday & Friday).

Compensation

The base compensation for this position is $130,000.00 – $160,000.00 per year depending on experience and qualifications.

WHY PROSERVICE

ProService is a Hawaii-based PEO offering payroll, HR consulting, benefits administration, and back-office support to small and medium-sized businesses statewide — handling operational complexity so clients can focus on running their businesses. Backed by Silver Lake — one of the world's leading technology investors - 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 and leaders 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 (including volunteer time) - just to name a few.