Brokerage Operations Specialist

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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:

The Brokerage Operations Specialist is a subject matter expert in back-office mechanics in money movement and securities transactions. While your manager architects the framework, you own the investigative loop, navigate unusual circumstances and resolve breaks. This role is a critical member of the team, responsible for ensuring Gusto broker-dealer entity’s accuracy and regulatory compliance of day-to-day movement of customer funds, securities transaction reconciliation and remediation, and regulatory reporting requirements. This role also requires meticulous attention to detail and a commitment to process excellence

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:

• Own the daily operational lifecycle: You will independently manage the daily flow of customer funds and securities transactions between Gusto’s broker-dealer entity and our banking/clearing partners. You are responsible for ensuring every transaction meets our strict Internal Control Over Compliance (ICOC) standards.
• Investigative Exception Management Rather than just processing data, you will handle high-stakes exceptions. You’ll manage money movement that requires professional judgment (e.g., complex stop-and-reissue checks, manual payment releases, ACH reversals, securities settlement breaks, net-capital calculation discrepancy), ensuring regulatory deadlines and customer expectations are met without sacrificing accuracy.
• Control Evidencing & Audit Readiness: You will independently perform daily, monthly and quarterly reconciliations for customer account statements, dividends, and security counts. You’ll prepare and review the evidence for these controls, ensuring it is robust enough to withstand scrutiny from independent auditors and regulators.
• Cross-Functional Collaboration: You will act as the eyes and ears on the ground, recommending product solutions to our Engineering and Product teams on how manual workarounds can be translated into automated code. You will engage with our external banking/clearing partners to  resolve difficult operational matters.

Here’s what we're looking for:

• 5+ years of experience in a financial operations, treasury, or back-office role, preferably within a carrying  broker-dealer or registered investment adviser environment.
• Required Licensing: FINRA SIE + Series 99
• 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)
• Knowledge of cash and securities handling, settlement processes, and regulatory reporting requirements is a plus.
• Proven ability to perform 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 daily, monthly, and quarterly operational cycles.
• Demonstrated ability to function at the Integrator level of AI fluency, consistently applying AI tools to complex analytical and operational tasks to drive efficiency and measurement accuracy.
• A Bachelor’s degree in Finance, Accounting, Business, or a related field.

Our cash compensation range for this role is $102,130 to $120,000 in New York, NY. Final offer amounts are determined by multiple factors including candidate location, experience, and expertise.

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. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. 

Gusto is proud to be an equal opportunity employer. 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. We want to see our candidates perform to the best of their ability. 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.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.