Retirement Compliance Specialist

<div class="content-intro"><p style="line-height: 1.2;">&nbsp;</p> <hr> <p><strong>About Gusto</strong></p> <p>At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.</p> <p>&nbsp;<br>All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our<a href="https://gusto.com/about/careers/total-rewards" target="_blank"> <u>Total Rewards philosophy</u></a>.</p> <p>&nbsp;<br>AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.</p></div><p><strong>About the Role:</strong></p> <p>As a Retirement Compliance Specialist, you'll serve as a subject-matter expert on ERISA compliance and 401(k) plan administration within Gusto's Retirement Services organization. This role will be part of the Retirement Compliance team that focuses on the work that needs specialist judgment: independent quality assurance, training, complex corrections, and consultation on ambiguous or high-risk plan provisions.</p> <p>You'll be a trusted resource across the business, translating dense legal plan documents and ERISA requirements into guidance that Sales, Conversion Ops, and Customer Experience teams can act on confidently</p> <p><strong>About the Team:</strong></p> <p>The Retirement Compliance team ensures every 401(k) plan Gusto administers stays compliant with IRS and ERISA requirements, from conversion through ongoing operation. We utilize AI to shift towards higher-value, specialist work: quality assurance, training, escalation support, and complex ERISA analysis. You'll work closely with Conversion Ops, Sales, and Legal &amp; Compliance, and you'll help shape the tools and processes the broader organization relies on as this transition continues.</p> <p><strong>Here’s what you’ll do day-to-day:</strong></p> <ul> <li>Serve as the ERISA/compliance escalation point for Conversion Ops and Sales on complex plan provisions, eligibility questions, and Adoption Agreement interpretation.</li> <li>Own end-to-end quality assurance for the plan review process <em>— </em>validating each build against the signed Adoption Agreement, and developing the internal tooling and business rules that support the review process at scale.&nbsp;</li> <li>Conduct plan reviews for new and converting 401(k) plans, translating complex legal plan documents into clear, accurate guidance for internal teams and customers.</li> <li>Build and deliver internal training and reference materials so Conversion Ops, Sales, and Customer Experience teams can handle routine plan questions independently.</li> <li>Partner with Legal &amp; Compliance on regulatory interpretation and sign-off for higher-risk plan changes.</li> <li>Identify and champion opportunities to use AI tools and automation to reduce manual review time while strengthening accuracy across plan setup and compliance workflows.</li> </ul> <p><strong>Here’s what we're looking for:</strong></p> <ul> <li>3–5 years of experience in 401(k)/defined contribution plan administration, compliance, or ERISA&nbsp;</li> <li>Strong working knowledge of IRS and ERISA regulations governing retirement plans, including eligibility, testing, and corrections.</li> <li>Experience reviewing plan documents (Adoption Agreements, plan provisions) and translating them into operational guidance.</li> <li>Comfort partnering cross-functionally with Sales, Conversion Ops, and Legal &amp; Compliance on ambiguous, escalated issues.</li> <li>Strong written and verbal communication skills — able to distill complex ERISA concepts for audiences without a compliance background.</li> <li>Experience building training materials or documentation for non-specialist teams.</li> <li>AI literacy: comfortable using and helping refine AI-assisted tools for plan review and setup, and identifying where automation can responsibly take on routin