Head of Brokerage Operations

About Gusto 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 . About the Role: As the Founding Operations Leader at Gusto's broker-dealer entity, you will be the primary architect of our in-house carrying broker-dealer operations. You aren't here to follow a manual; you are here to write it. You will establish the operational objectives, policies, and work plans from the ground up, ensuring our AI-native infrastructure meets the highest standards of FINRA/SEC compliance and protect customers’ assets. You will report to and partner with the Head of Gusto's broker-dealer entity. You will build our operational blueprint serving as the bridge between customer impact, technical innovation and regulatory rigor. You will design, oversee and execute essential back-office functions, focusing on the accurate movement of customer funds, transaction reconciliation and remediation, and reporting required for our broker-dealer entity. This role requires meticulous attention to detail, a commitment to process excellence and efficiency, and proven ability to lead and scale operational processes. About the Team: Gusto’s broker-dealer entity, a registered broker-dealer owned by Gusto Inc, forms the foundation for Gusto to expand our product offerings in retirement and investment. Gusto’s broker-dealer entity acts as the custodian of customers’ retirement assets and facilitates money movement and securities transactions, by integrating with the banking rails and clearing rails in the financial system. As a collaborative and technical group, we focus on designing, implementing, and monitoring the proprietary system and processes that meet the evolving demands of the retirement industry and regulatory landscape. You will join a team committed to building operational solutions that scale with Gusto’s mission to serve the small business economy. Here’s what you’ll do day-to-day: Establish Operational Architecture: Author and implement the foundational operational objectives, policies, and procedures for our carrying broker-dealer. You will design the "0-to-1" work plans for money movement and trade clearing that will scale as we grow. Strategic Escalation Decision Making: Serve as the final authority on operational exceptions. You will apply sophisticated judgment to resolve unusual circumstances where no precedent exists, understanding that your decisions directly impact Gusto’s results and long-term regulatory standing. Examples are complex stop-and-reissue checks, manual payment releases, ACH reversals, securities settlement breaks, net-capital calculation discrepancy), Controls Audit Governance: Architect and maintain an operational control environment that meets the rigorous standards comparable to publicly traded companies. You will ensure that Gusto broker-dealer entity’s Internal Controls Over Compliance (ICOC) are robust, evidenced, and audit-ready by design for every customer transaction, setting a high bar for operational excellence. You will ensure that the transaction data produced is of the highest integrity, as it serves as a critical upstream feed into Gusto’s consolidated financial statements. You recognize that the quality of your team's work product directly affects our annual audits conducted by an independent PCAOB auditor, and has far-reaching implications to Gusto’s overall corporate governance. Cross-Functional Collaboration, Influence Impact: Orchestrate complex partnerships with Engineering, Product, Legal, Compliance, FinOp, Accounting and FPA to build Gusto’s first-of-its-kind carrying broker-dealer. You are an ex ... (truncated, view full listing at source)