Director of Benefit Services

ProService is seeking a Director of Benefits Services to lead the end-to-end execution of healthcare and voluntary benefits administration across our client base. This is an operational leadership role — you'll own the department's priorities, drive them to execution, and be accountable for the quality, compliance, and client experience of everything that runs through your team.

What makes this role demanding is the intersection of regulatory complexity, high transaction volume, and open enrollment seasonality — all within a fast-moving, client-centric environment where ownership and follow-through are non-negotiable. You'll be expected to lead with both urgency and care, continuously simplify operations, and build a team capable of performing at a high level year-round.

IN THIS ROLE YOU WILL

• Translate company and departmental priorities into a focused operating plan — setting clear goals around enrollment performance, quality, and open enrollment execution, and course-correcting quickly when results fall off track

• Identify and eliminate root causes of inefficiency across benefits workflows, carrier integrations, payroll/HRIS handoffs, and client communications — simplifying, automating, and scaling what works

• Coach and develop team members through timely feedback, structured development plans, and clear performance expectations — addressing gaps early and investing in growth for high performers
• Own output quality by defining and enforcing standards for eligibility determinations, enrollment processing, regulatory compliance (ACA, ERISA, COBRA, HIPAA), and case documentation
• Run a disciplined operating rhythm — daily huddles, weekly scorecard reviews, monthly check-ins — so the team always knows exactly how they're performing against goals
• Lead the integration of healthcare and voluntary benefits into a single-contact client service model, championing tool adoption and holding the team to high standards of execution

IS THIS ROLE RIGHT FOR YOU?

We want you to walk in with clear eyes. Here's an honest look at what this role is — and what it isn't. This is a high-accountability operational leadership role where you're measured by what your team delivers, not just what you direct. Benefits compliance — ACA, ERISA, COBRA, HIPAA — isn't background noise here; it's central to the work. And open enrollment isn't just a busy season — it's months of preparation culminating in execution that has to be flawless under real pressure. What this role is not is a strategy-only seat. You'll be in the work: auditing cases, inspecting quality, and personally holding the operating rhythm. Performance issues don't get deferred here — you're expected to identify and address underperformance directly and early.

WHAT YOU'LL BRING TO THE TEAM

We're looking for a proven operational leader with deep benefits expertise and a track record of building high-performing teams. Prior benefits administration experience is required; PEO experience is a strong plus.

• You've led benefits operations in a high-volume environment and can point to specific improvements in accuracy, efficiency, or team performance you owned from start to finish
• You have deep working knowledge of healthcare and voluntary benefits, eligibility rules, carrier integrations, and regulatory requirements — ACA, ERISA, COBRA, and HIPAA aren't acronyms you're learning on the job
• You're a people developer who addresses performance directly — you've managed underperformers, retained top talent, and built teams that perform through high-volume seasons without falling apart
• You find inefficiency and fix it. You ask why processes are the way they are, and you have examples of simplifying workflows, improving data integrity, or removing friction that was costing the team time and accuracy
• Difficult conversations don't derail you. You've navigated escalations, cross-functional friction, and underperformance with clarity and accountability — without pushing hard calls upward

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), as well as fully remote candidates based on the US Mainland. Remote candidates must be available during Hawaii Standard Time (HST / UTC-10) business hours, and located within California, Washington, Oregon, Idaho, and Nevada (PST).

COMPENSATION

The base compensation for this position is $155,000 – $190,000 annualized depending on 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 Hawaii. Backed by Silver Lake and recognized as one of Hawai?i'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 Hawai?i.

• 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.

• Real ownership and impact — your work connects directly to the bigger picture, and you'll see exactly how your contributions move the needle.
• Room to grow — internal roles post first, and we reimburse certifications, conferences, and memberships. Your growth is our growth.
• Competitive total rewards — fully paid healthcare (Kaiser/HMSA), unaccrued PTO, 401(k) with 4% match, 12 weeks paid parental leave, student loan assistance, and more.