PEO Benefits Compliance Senior Lead

Gusto•San Francisco, NY

19d•$112,000 - $167,000•Hybrid

About The Position

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . Benefits Compliance PEO Lead About the Team The Benefits Compliance team is are the forefront of supporting Gusto’s benefits products. We work closely with Product, Legal, and Operations to interpret regulations, guide implementation, and support enterprise compliance. About the Role We’re looking for a Benefits Compliance PEO Lead to support a complex, multi-entity benefits and co-employment model that spans health benefits, insurance programs, and state-specific employer obligations. This role will be responsible for designing, implementing, and maintaining compliance programs across bundled benefits and employer-sponsored insurance offerings, working closely with Legal, Product, Operations, and external partners. This is a hands-on, highly cross-functional role suited for someone who has previously supported compliance for cPEO or co- employment structures and understands how benefits, insurance, and employment laws intersect at scale. This role requires a deep understanding of how benefits compliance, insurance regulation, and employment law intersect, and the ability to navigate those interdependencies in a complex, multi-state environment. You will be responsible for identifying, assessing, and addressing regulatory requirements that span multiple policy disciplines — including health benefits, workers’ compensation, unemployment insurance, and state disability programs — and translating those requirements into scalable solutions. Here’s what you’ll do day-to-day: Strategic Leadership & Vision: Develop and execute comprehensive compliance strategies across integrated benefits and employment-related insurance programs, aligning with Gusto’s broader business objectives and growth plans. Anticipate emerging regulatory trends across health benefits, workers’ compensation, unemployment insurance, and state disability programs, and proactively identify compliance risks and operational pain points. Guide the development of policies, frameworks, and approaches that position Gusto to scale responsibly while maintaining strong regulatory standing. Advanced Regulatory Analysis & Program Management: Lead complex compliance initiatives spanning multiple regulatory domains and jurisdictions. Operationalize statutes, regulations, and guidance, and in determining appropriate compliance approaches where precedent may be limited or evolving. Understand the full lifecycle of regulatory requirements and assess downstream impacts across products, systems, and customer experiences. Cross-Functional Leadership: Direct collaborative efforts with internal teams including Product, Legal, and Compliance to translate complex policy implications into actionable business insights. Establish methods, processes, and controls for addressing new or evolving compliance challenges, ensuring alignment with departmental and company-level objectives. Provide creative, practical solutions by understanding the interrelationships between benefits compliance, insurance regulation, and business initiatives. Guidance & Mentorship: Serve as a senior subject matter expert on benefits and employment-related insurance compliance. Frequently advise stakeholders across the organization on complex regulatory questions, helping teams navigate ambiguity with confidence. May guide or mentor other team members and contribute to the development of compliance best practices, standards, and playbooks. Here’s what we're looking for: Core Experience & Expertise 8+ years of experience in benefits compliance, insurance regulation, or a closely related field, with deep expertise in multi-employer insurance arrangements, brokerage and plan administrative health insurance compliance (small group and/or mid-market preferred). Demonstrated experience supporting regulated insurance products at scale, including multi-state health insurance offerings, multi-employer arrangements, or agency compliance obligations. Strong working knowledge of federal and state insurance regulations, including ERISA, ACA, market conduct rules, producer licensing and appointment requirements, and anti-rebating laws. Experience navigating compliance for complex or consolidated business models. Proven ability to conduct independent regulatory research, interpret statutes, regulations, bulletins, and regulator guidance, and assess applicability to new or evolving products. Skilled at operating in areas with regulatory ambiguity or limited precedent. Experience monitoring and anticipating regulatory changes across federal and state insurance departments and translating those developments into actionable compliance strategies. Strong track record of partnering with Product and Operations teams to inform product design and roadmap decisions from a compliance perspective. Ability to translate regulatory requirements into practical, risk-adjusted, and scalable product and operational requirements. Experience reviewing and advising on product flows, enrollment experiences, disclosures, and system controls to ensure compliance is embedded by design. Demonstrated ability to own and drive complex compliance programs end-to-end Comfortable establishing processes, controls, and documentation that support auditability, regulator inquiries, and sustainable scale. Experience serving as a senior subject matter expert, providing clear guidance to cross-functional stakeholders and influencing decision-making at multiple levels. Excellent written and verbal communication skills, with the ability to explain complex regulatory concepts to non-legal audiences. Strong collaborator who can build trust across Legal, Product, Operations, Marketing, and external partners, and navigate competing priorities with pragmatism. Experience mentoring or informally guiding other compliance professionals, contributing to shared standards, playbooks, or best practices. Preferred Experience working with or supporting digital or technology-enabled insurance platforms. Familiarity with state DOI interactions, market conduct exams, or regulatory inquiries.

Requirements

8+ years of experience in benefits compliance, insurance regulation, or a closely related field, with deep expertise in multi-employer insurance arrangements, brokerage and plan administrative health insurance compliance (small group and/or mid-market preferred).
Demonstrated experience supporting regulated insurance products at scale, including multi-state health insurance offerings, multi-employer arrangements, or agency compliance obligations.
Strong working knowledge of federal and state insurance regulations, including ERISA, ACA, market conduct rules, producer licensing and appointment requirements, and anti-rebating laws.
Experience navigating compliance for complex or consolidated business models.
Proven ability to conduct independent regulatory research, interpret statutes, regulations, bulletins, and regulator guidance, and assess applicability to new or evolving products.
Skilled at operating in areas with regulatory ambiguity or limited precedent.
Experience monitoring and anticipating regulatory changes across federal and state insurance departments and translating those developments into actionable compliance strategies.
Strong track record of partnering with Product and Operations teams to inform product design and roadmap decisions from a compliance perspective.
Ability to translate regulatory requirements into practical, risk-adjusted, and scalable product and operational requirements.
Experience reviewing and advising on product flows, enrollment experiences, disclosures, and system controls to ensure compliance is embedded by design.
Demonstrated ability to own and drive complex compliance programs end-to-end
Comfortable establishing processes, controls, and documentation that support auditability, regulator inquiries, and sustainable scale.
Experience serving as a senior subject matter expert, providing clear guidance to cross-functional stakeholders and influencing decision-making at multiple levels.
Excellent written and verbal communication skills, with the ability to explain complex regulatory concepts to non-legal audiences.
Strong collaborator who can build trust across Legal, Product, Operations, Marketing, and external partners, and navigate competing priorities with pragmatism.
Experience mentoring or informally guiding other compliance professionals, contributing to shared standards, playbooks, or best practices.

Nice To Haves

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

Responsibilities

Develop and execute comprehensive compliance strategies across integrated benefits and employment-related insurance programs, aligning with Gusto’s broader business objectives and growth plans.
Anticipate emerging regulatory trends across health benefits, workers’ compensation, unemployment insurance, and state disability programs, and proactively identify compliance risks and operational pain points.
Guide the development of policies, frameworks, and approaches that position Gusto to scale responsibly while maintaining strong regulatory standing.
Lead complex compliance initiatives spanning multiple regulatory domains and jurisdictions.
Operationalize statutes, regulations, and guidance, and in determining appropriate compliance approaches where precedent may be limited or evolving.
Understand the full lifecycle of regulatory requirements and assess downstream impacts across products, systems, and customer experiences.
Direct collaborative efforts with internal teams including Product, Legal, and Compliance to translate complex policy implications into actionable business insights.
Establish methods, processes, and controls for addressing new or evolving compliance challenges, ensuring alignment with departmental and company-level objectives.
Provide creative, practical solutions by understanding the interrelationships between benefits compliance, insurance regulation, and business initiatives.
Serve as a senior subject matter expert on benefits and employment-related insurance compliance.
Frequently advise stakeholders across the organization on complex regulatory questions, helping teams navigate ambiguity with confidence.
May guide or mentor other team members and contribute to the development of compliance best practices, standards, and playbooks.