Compliance and Regulatory Manager

About the role

Own the compliance function end-to-end, partnering closely with the Chief Counsel and Corporate Counsel to build regulator relationships, shape legislative strategy, drive first-to-market insurance products through approval, and keep every deadline across every function.

Responsibilities

• 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.

Requirements

• 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.

Qualifications

• You’re a problem solver with a track record of zero-defect filings across concurrent deadlines.
• You’ve 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 and 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, keeping leadership informed and protecting organizational interests.
• 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.
• You’ve leaned on you because of your follow-through record — not just your title or background.

Skills

• Strong legal and compliance skills.
• Excellent communication and relationship-building abilities.
• Ability to manage multiple priorities and deadlines.
• Experience with HR and payroll systems.
• Knowledge of insurance laws and regulations.
• Experience with M&A processes.

Benefits

• Flexible hybrid schedule.
• Competitive compensation range of $130,000 – $160,000 per year, commensurate with experience and qualifications.
• Performance-based compensation system.
• Internal roles and reimbursement for certifications, conferences, and memberships.
• Comprehensive total rewards package including fully paid healthcare, 401(k) matching, paid parental leave, student loan assistance, employee assistance programs, and paid time off.

Pay

$130,000 – $160,000 per year, commensurate with experience and qualifications.

Schedule

Hawaii Kai, Oahu — Hybrid