Brokerage Operations Specialist

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 400,000 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.

Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

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.

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

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.