PEO Compliance Lead - Benefits Product

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.

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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.

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.

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.

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