Director of Health Plan Compliance

Director of Health Plan Compliance | Remote, Full-Time

About the role

Health Rosetta is fixing broken health care by helping employers build and manage high-performance health plans. This director-level role owns how we help self-funded employers and their advisors meet, and get ahead of, their compliance obligations. You'll be the senior voice on compliance for our clients, our team, and the products we build. You'll own the domain expertise and delivery for RosettaProtect, our compliance solution: what it knows and how well it serves the employers who rely on it.

This isn't about maintaining an established program. Much of what we do, and how we do it, is being built now. You'll set the standard for excellent compliance support for self-funded plans, then turn that into repeatable processes, product, and increasingly into knowledge that AI-assisted workflows can carry out reliably. You'll work closely with our product team, Customer Success Managers, compliance team, and outside legal counsel.

What you'll own

Compliance leadership

• Serve as the senior escalation point for complex compliance questions from clients, advisors, and internal teams, and make the call on how we respond, including when a matter belongs with legal counsel
• Own our compliance program substance: which requirements we cover, how we evaluate client submissions, what "complete" means, and how we communicate risk
• Anticipate regulatory change across ERISA, ACA, CAA, MHPAEA, HIPAA, COBRA, IRC, and state requirements; decide what it means for clients; get it into guidance and products before they have to ask
• Lead the hardest work: MHPAEA NQTL analyses, CAA obligations, nondiscrimination testing, plan document and SPD review
• Lead compliance reviews of health plan vendors and solutions, with attention to contract terms affecting plan sponsors' fiduciary duties

RosettaProtect domain expertise and delivery

• Own the compliance knowledge behind RosettaProtect. You're accountable for accuracy, completeness, and currency of all requirements, rules, guidance, and content the product delivers
• Own client delivery of RosettaProtect. Define service standards, onboarding, and compliance calendars; partner with Customer Success Managers to deliver them; be accountable for quality and timeliness
• Act as the product's domain lead with our engineering team: define what clients need, shape how we solve it, write requirements product builders can act on
• Translate expertise into structured, testable knowledge (checklists, decision logic, rules, worked examples) that software and AI-assisted workflows can use reliably
• Find manual work that shouldn't exist, then design, test, and validate automation to replace it

Team and market

• Mentor our compliance team, set quality standards, establish review practices that scale as we grow
• Represent Health Rosetta's compliance perspective with advisors, employers, and partners, including at RosettaFest and through educational content
• Contribute to open knowledge and standards for high-performance health plans in partnership with Nautilus Health Institute

What you bring

• Deep domain expertise in major laws affecting employer-sponsored health plans (ERISA, ACA, COBRA, HIPAA, FMLA, MHPAEA, CAA, IRC, insurance requirements). You understand how they interact, where gray areas exist, and how they play out in self-funded plans. Others come to you when the answer isn't in the guidance.
• Client focus with real follow-through. You design systems that keep an entire book of clients on track, not just your own work.
• Product sensibilities. You understand market needs, solve them creatively, and show product builders what good solutions look like by sketching workflows, writing rules, or testing output yourself.
• Clear communication. You explain hard issues to CFOs in two minutes, then write precisely enough for attorneys or software specifications.

Who you are

• Purpose-driven. Our mission requires taking harder paths. You need genuine motivation to do meaningful work beyond personal interests.
• You thrive in high uncertainty. "How to do it well" doesn't exist yet for much of what we're doing. You love uncertainty and create clarity within it for yourself and others.
• Patience of a monk, urgency of a rabbit. You tackle complex, multi-year systemic problems while moving at startup pace day-to-day.
• Deeply curious and driven to solve hard problems. Market change is fast. AI-guided work is emerging. This moment pairs curiosity and problem-solving into outsized impact.
• Judgment-informed ambition. As implementation costs drop, ambition rises. You pair ambition with sound judgment about what truly matters and what to say no to.
• Strategically lazy. You hate manual repetitive work enough to automate it.
• You sweat details. This is health plan compliance. Enough said.

Required experience

• 8+ years in employee benefits compliance, health and welfare plans, or equivalent regulatory field, including substantial self-funded plan experience
• Track record serving as the go-to expert or escalation point for complex compliance matters at consulting firms, TPAs, carriers, law firms, or plan sponsors
• Hands-on experience with MHPAEA, CAA, ACA requirements, and reviewing plan documents and SPDs
• Built or substantially improved a compliance program, service line, or workflow
• Sound judgment about the line between compliance guidance and legal advice; effective collaboration with ERISA counsel
• Exceptional written and verbal communication skills with executives, advisors, and attorneys

Preferred experience

• JD or legal training in ERISA and employee benefits (this role is not legal counsel)
• Professional credentials such as CEBS or GBA
• Experience working with product or engineering teams, writing requirements, or contributing to compliance software
• Practical experience using AI tools for research, document review, or workflow automation
• Experience reviewing TPA, PBM, or other vendor contracts
• Experience managing or mentoring compliance professionals
• Speaking, writing, or teaching on benefits compliance

How to apply

Send your resume and a cover letter to View email address on click.appcast.io. In your cover letter, tell us why this role interests you and describe a compliance problem you faced where there was no established playbook: what you did, what you built, and what you would do differently next time. Applications submitted through LinkedIn only will not be considered.

Equal Opportunity

Health Rosetta is committed to an equitable, inclusive workplace. We hire based on qualifications and capability without regard to race, color, religion, sex, gender identity, pregnancy, family status, sexual orientation, age, national origin, marital status, citizenship, disability, veteran status, or other legally protected characteristics.