Compliance Specialist

About the role: Health Rosetta is fixing broken health care by helping employers build and manage high-performance health plans. We move fast on hard problems. This remote role supports Rosetta Protect (our compliance platform) and helps employer clients navigate ERISA, ACA, HIPAA, COBRA, FMLA, MHPAEA, and related compliance requirements. You'll split your time: 60% supporting Rosetta Protect workflows and client submissions. 40% responding to compliance questions from clients and internal teams. You'll contribute to client work immediately - expect a fast ramp to ownership.

What you'll do: Evaluate client compliance submissions against federal/state requirements and clearly explain next steps Answer day-to-day compliance questions in plain language that clients actually understand Track deadlines and follow-up across multiple employer groups Identify compliance gaps and help determine appropriate filings, notices, or corrective steps Research and monitor changes in health plan regulations Review/prepare plan documents, SPDs, SMMs, notices, and compliance materials Escalate complex legal questions to counsel (we'll define the threshold together)Recommend and implement improvements to Rosetta Protect and internal processes Who we need 3+ years working with employee benefits compliance, health and welfare plans, or equivalent regulatory experience Strong working knowledge of ERISA, ACA, COBRA, HIPAA, FMLA, MHPAEA, IRC, and insurance requirements Proven ability to turn regulatory findings into clear action steps for clients Excellent written and verbal communication - you translate complexity into guidance Can manage multiple priorities and detailed work independently in a remote environment Comfortable in an evolving environment; you build structure and improve processes as you learn Must have Self-funded health plan experience Background in compliance program development, workflow design, or software tools Technical writing, project management, or customer success experience

Our culture: We're purpose-driven, which means we take harder paths to solve systemic problems because we genuinely care about meaningful work beyond the paycheck. That kind of mission-focused mindset is essential here. You'll work in high uncertainty - we thrive on it - tackling complex, multi-year problems while moving at startup pace on day-to-day execution. You're naturally curious about hard problems and driven to solve them, and you hate manual repetitive work enough to automate it. The flip side: this is health plan compliance, where details directly impact our clients. You need to care about getting them right. 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.

How to apply: Send your resume and a cover letter to careers@healthrosetta.org. In your cover letter, tell us why this role interests you and share an example of how you've helped a client or improved a process in an evolving work environment. Applications submitted solely through Linked In only will not be considered.