Senior Product Compliance Analyst

About Lively

Lively set out to raise the bar on benefit solutions, because we believe no one should have to sacrifice personal wellness for financial wellness. While traditional benefits focus more on transactions and less on the humans using them, Lively harnesses user-centric design and innovative technology to deliver an effortless experience for employers and account holders alike. Our modern HSA is consistently top-rated, and we have since expanded our offerings to provide a full suite of other benefits and services for companies, consumers, and financial institutions.

Lively is a remote-first company, headquartered in San Francisco with employees across the US. Come join us and help make getting the value out of your benefits as simple as it should be.

Wyoming residency (Mountain Time Zone) preferred but not required (Lively operates a Wyoming-chartered trust company, and proximity to Wyoming regulatory contacts is a big plus)

About the Role

Lively's HSA, FSA, and HRA products are the core of our business and our most complex from a regulatory perspective. We are looking for a Senior Product Compliance Analyst to join our Legal & Compliance team as the go-to compliance resource for these products, ensuring they are designed, marketed, and delivered in compliance with applicable regulatory requirements. You will review marketing materials and customer-facing content relevant to your areas of specialization for compliance with consumer protection laws. You will lead compliance risk assessments for new product features and platform developments, including AI-powered tools, and assist with audits. You will field regulatory questions from internal teams, support customer escalations with compliance dimensions, and develop deep expertise in how Lively's benefit products operate, including the transaction and payment infrastructure that supports them. You will work closely with our Senior Product Compliance Manager, who leads compliance for COBRA, commuter, and lifestyle spending account programs. Together, you will ensure comprehensive compliance coverage across Lively's product suite. You report to the Head of Legal & Compliance.

Responsibilities

Internal Subject Matter Expertise: Develop deep expertise in Lively's benefit products and serve as an internal compliance resource for Product, Engineering, Customer Success, Member Services, and Sales teams. Answer ad hoc questions about benefits compliance and regulatory requirements. Review marketing materials and customer-facing content for your areas of specialization to ensure UDAAP compliance and regulatory accuracy.

• Benefits and Transaction Compliance: Develop expertise in how Lively's benefit products operate end-to-end, including how funds flow into and out of accounts. Serve as a compliance advisory resource for operational teams (Banking Ops, Account Ops, Card Ops) when questions arise at the intersection of benefits regulations and transaction processing.
• Risk Management: Lead compliance risk assessments for new product features, platform developments, workflow changes, and emerging technologies such as AI-powered tools.
• Evaluate whether product changes introduce regulatory risk for your assigned benefit products and recommend controls or design modifications. Track mitigation and remediation of identified risks.
• Identify privacy implications, including HIPAA and data privacy considerations, and escalate as appropriate.
• Regulatory Monitoring: Monitor regulatory developments and produce actionable impact assessments for affected teams.
• Escalation Support: Support internal teams in resolving customer escalations and employer questions that involve regulatory considerations related to your areas of expertise.

Skills & Experience

• 4-6 years in product compliance, regulatory affairs, or benefits administration at an HSA custodian, TPA, benefits administrator, health plan, or fintech.
• Strong working knowledge of benefits regulatory requirements for tax-advantaged accounts (HSA, FSA, HRA).
• Familiarity with how benefit account transactions are processed (ACH, card networks) is a plus.
• Demonstrated ability to interpret legal advice, IRS guidance, DOL advisory opinions, or similar regulatory materials and translate them into product requirements for lay audiences.
• Strong verbal and written communication skills; comfortable fielding live compliance questions and producing clear regulatory impact assessments.
• Comfortable operating as an embedded compliance partner across product, engineering, sales, and customer success teams.
• Adaptable in a fast-paced environment with high volume during Open EnrollmentFamiliarity with HIPAA, GLBA, or consumer data privacy requirements as they apply to benefits administration is a plus

Applicants must be currently authorized to work in the United States on a full-time basis with no sponsorship needed now, or in the future.

We encourage you to apply even if you do not meet all of the qualifications, but feel you would be a good fit for the position.