Director of Compliance, Employee Benefits-Insurance Advisory Solutions

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director of Compliance, Employee Benefits-Insurance Advisory Solutions based in the United States.

This senior-level role provides legal and regulatory compliance guidance across employer-sponsored health and welfare benefit programs.

You will serve as a key subject matter expert for federal and state requirements, with particular responsibility for California-specific compliance.

The position combines sophisticated legal analysis with practical client counseling, education, and business support.

You will partner with compliance professionals, advisors, client experience teams, and senior stakeholders across the West region.

The role also offers the opportunity to influence large-scale compliance initiatives, client deliverables, and sales-support activities.

As a senior leader, you will mentor junior compliance professionals and contribute to the development of a high-performing compliance function.

This is an opportunity to turn complex and evolving regulations into clear, actionable guidance that helps clients navigate employee benefits requirements with confidence.

Accountabilities:

• Provide senior-level legal and regulatory compliance guidance on federal and state health and welfare employee benefits requirements, serving as a trusted subject matter resource for clients and colleagues.
• Lead and coordinate compliance activities and projects across the West region, partnering with the National Compliance Team to support large-scale initiatives and day-to-day operational needs.
• Serve as a subject matter expert on California-specific employee benefits compliance, including state and local requirements affecting employer-sponsored health and welfare programs.
• Monitor, review, and interpret evolving legislation, regulations, regulatory guidance, and litigation developments, translating complex requirements into practical recommendations and actionable guidance.
• Develop, draft, and deliver client-facing and colleague-facing resources, including regulatory summaries, statutory interpretations, compliance alerts, presentations, educational materials, checklists, and other compliance communications.
• Support clients and prospects by explaining complex legal and regulatory requirements in a clear and accessible manner, including through training sessions, workshops, seminars, and individual consultations.
• Partner with advisors and client experience teams on sales initiatives, prospect meetings, finalist presentations, educational sessions, and client relationship activities across the West region.
• Coordinate the timely and accurate delivery of large-scale compliance projects and resources while managing competing priorities, deadlines, and high volumes of client inquiries.
• Mentor and guide junior compliance team members across project management, legal research, drafting, public speaking, professional development, and interpretation of regulatory and industry developments.
• Collaborate with colleagues across the national compliance function to promote consistent approaches, share expertise, and strengthen compliance practices.
• Create and maintain compliance materials, forms, presentations, graphical interpretations, and other resources using Microsoft Office and related software applications.
• Identify and communicate the practical impact of new legal and regulatory developments on employer benefit programs and help stakeholders respond effectively.
• Support continuous improvement of compliance processes, client education, internal resources, and service delivery across the region.

Requirements

• Advanced graduate degree required, such as a Master’s, J.D., or Ph.D.; a Juris Doctor is strongly preferred.
• Minimum of 10 years of relevant experience in health and welfare employee benefits compliance, with significant experience advising on California-specific requirements strongly preferred.
• Demonstrated expertise across a broad range of federal and state laws, regulations, statutes, ordinances, and regulatory requirements affecting employer-sponsored health and welfare benefit programs.
• Strong knowledge of California health and welfare requirements, including SFHCSO, Cal-COBRA, California disability and paid family leave requirements, applicable state and local leave laws, and other California-specific mandates.
• Ability to monitor and interpret evolving California legislation and regulations and explain their practical implications for employer-sponsored benefit programs.
• Strong understanding of federal and state regulatory agencies, legislative processes, executive branch authorities, and regulatory rulemaking.
• Proven ability to quickly analyze, draft, edit, and communicate complex legal, regulatory, and litigation matters to non-legal audiences.
• Strong leadership and project management skills, including the ability to own large-scale deliverables from planning through timely and accurate completion.
• Ability to mentor junior professionals and provide guidance across legal research, drafting, project execution, presentations, and professional development.
• Excellent organizational skills and the ability to manage multiple priorities, deadlines, client requests, and projects in a fast-paced environment.
• Exceptional written and verbal communication skills, with the ability to translate sophisticated legal concepts into concise, practical business guidance.
• Proficiency in developing professional documents, alerts, checklists, presentations, and other compliance resources using Microsoft Office and related software.
• Strong client service orientation and the ability to manage a high volume of client-facing correspondence, compliance inquiries, presentations, training sessions, and follow-up requests.
• Understanding of sales and prospecting processes, with the ability to support client education, finalist presentations, prospect meetings, and relationship development activities.
• Ability to work collaboratively across a national compliance organization while independently managing regional responsibilities and priorities.

Benefits

• Starting salary of $185,000, with compensation negotiable at the time of offer.
• Fully remote position based in the United States.
• Negligible location-related constraints associated with a remote work environment.
• Opportunity to serve as a senior compliance advisor supporting complex employee benefits matters across a major U.S. region.
• High-impact role combining legal expertise, client advisory work, leadership, education, and business development support.
• Opportunity to develop deep expertise in California-specific employee benefits compliance while advising on broader federal and state requirements.
• Collaborative environment with exposure to national compliance professionals, benefits advisors, client teams, and senior stakeholders.
• Leadership opportunity to mentor junior compliance professionals and contribute to the continued development of compliance capabilities.
• Opportunity to support clients across employee benefits, insurance, and risk management needs while translating complex regulations into practical solutions.
• Inclusive workplace committed to equal employment opportunity and a culture that values diverse perspectives and professional expertise.