Head of Operations & Business Management

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.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. 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 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 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.

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.

Author and implement the foundational operational objectives, policies, and procedures for our carrying broker-dealer. 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,

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

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.

10+ years of experience in a financial operations, treasury, or back‑office role, with at least 5 years in a leadership or managerial capacity, preferably within a carrying broker‑dealer or registered investment adviser environment.

In‑depth 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)

In‑depth 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.

A Bachelor’s degree in Finance, Accounting, Business, or a related field.

Our cash compensation range for this role is $177,020 to $208,000 in New York, NY. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2‑3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

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