About the Role

• Support a complex, multi-entity benefits and co-employment model involving health benefits, insurance programs, and employer obligations.
• Design, implement, and maintain compliance programs for bundled benefits and employer-sponsored insurance offerings.
• Work closely with Legal, Product, Operations, and external partners.
• Identify, assess, and address regulatory requirements across health benefits, workers2 compensation, unemployment insurance, and state disability programs.
• Translate regulatory requirements into scalable solutions.

Responsibilities

• Develop and execute compliance strategies aligning with business objectives and growth plans.
• Anticipate regulatory trends and identify compliance risks and operational challenges.
• Lead complex compliance initiatives spanning multiple regulatory domains and jurisdictions.
• Operationalize statutes, regulations, and guidance for compliance where precedents may be limited.
• Direct collaboration with Product, Legal, and Compliance teams to translate policy implications into business insights.
• Establish methods, processes, and controls for evolving compliance challenges.
• Provide creative and practical solutions understanding interrelationships between compliance, insurance, and business initiatives.
• Serve as a senior subject matter expert and advise stakeholders on complex regulatory questions.
• Guide or mentor team members and contribute to compliance standards and playbooks.

Requirements

• 8+ years experience in benefits compliance, insurance regulation, or related field.
• Expertise in multi-employer insurance arrangements, brokerage, and plan administrative health insurance compliance.
• Experience with multi-state health insurance offerings and agency compliance obligations.
• Strong knowledge of federal and state insurance regulations including ERISA, ACA, market conduct rules, licensing, and anti-rebating laws.
• Ability to conduct independent regulatory research and interpret statutes, regulations, and guidance.
• Experience navigating regulatory ambiguity with limited precedent.
• Experience monitoring and anticipating regulatory changes and translating them into compliance strategies.
• Strong partnership skills with Product and Operations to inform product design and compliance.
• Ability to translate regulatory requirements into risk-adjusted, scalable operational solutions.
• Experience owning complex compliance programs end-to-end, establishing processes for auditability and regulatory inquiries.
• Excellent communication skills and ability to explain complex concepts to non-legal audiences.
• Collaborative with ability to build trust across multiple teams and manage competing priorities.
• Experience mentoring or guiding other compliance professionals.

Preferred Qualifications

• Experience with digital or technology-enabled insurance platforms.
• Familiarity with state DOI interactions, market conduct exams, or regulatory inquiries.