Head of Brokerage Operations

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 FP&A to build Gusto’s  first-of-its-kind carrying broker-dealer. You are an expert at building consensus in sensitive regulatory environments, using data and operational insight to convince cross-functional stakeholders of the necessary balance between product innovation, execution velocity, uncompromising financial integrity and compliance requirements. You own the operational foundation that unlocks Gusto’s opportunities to expand our investment product offerings in 401(k), IRA and more diverse investment account types for Gusto’s member community to build wealth
• Fiscal Responsibility, Direction & Empowerment: Although you will start with building a small but mighty AI-native team, you’re responsible for establishing the team’s strategic direction, managing costs and demonstrating high ROI on the combination of headcount and AI agents. You’re also responsible for performance management and professional growth of the team, setting high bars for excellence and providing the coaching necessary to meet them.

Here’s what we're looking for

• 10+ years of experience in a financial operations, treasury, compliance operations, process optimization or back-office role, with at least 5 years in a project leadership or managerial capacity, within financial services or fintech companies.
• Required Licensing: possessing FINRA SIE + Series 7 + Series 24 currently; or ability to obtain FINRA SIE + Series 7 in two months and Series 24 in four months from the first date in the role.
• Some knowledge in SEC Rule 15c3-1 (Net Capital Rule), SEC Rule 15c3-3 (Customer Protection Rule), SEC Rule 17a-3 and 17a-4 (Recordkeeping Rule).
• Some knowledge of cash and securities handling, settlement processes, and regulatory reporting requirements is a plus.
• Proven ability to perform and oversee complex reconciliations and transaction research.
• High degree of comfort working with analytical tools, banking technology systems, clearing technology systems, and  financial data/reporting systems.
• Exceptional organizational skills and meticulous attention to detail to manage and strategically improve daily, monthly, and quarterly operational cycles.
• Demonstrated ability to use AI as a foundational part of work, not as an occasional extra. In practice, that means regularly applying AI to specific, well-defined tasks, using strong prompting techniques, critically evaluating and refining outputs, build long-running agents integrating with external tools and achieving clear efficiency gains in day-to-day work.
• Demonstrated ability to collaborate effectively with cross-functional stakeholders, external partners and regulators.
• Typical work schedule is 9am-5pm local time zone. Employees based in Denver are expected to occasionally start at 9:30am ET when US stock market opens if the team on the east coast is lacking coverage.
• A Bachelor’s degree in Finance, Accounting, Business, or a related field.

Our cash compensation range for this role is $150,640 to $177,000 in Denver, CO and $177,020 to $208,000 in New York, NY. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the level and amounts listed above.