The Brokerage Operations Specialist is a subject matter expert in back-office mechanics in money movement and securities transactions. 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.

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.
• Investigative Exception Management: You’ll handle high-stakes exceptions, 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.
• 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.

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.

Our cash compensation range for this role is $102,130 to $120,000 in New York, NY.

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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. 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.

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, 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.

• Required Licensing: FINRA SIE + Series 7 + Series 24.

• 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.

• 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.

• Demonstrated ability to collaborate effectively with cross-functional stakeholders, external partners and regulators.

• 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. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the level and amounts listed above.

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This role requires a strong analytical mindset, the ability to work independently toward defined objectives, and a high level of accountability with a hands-on execution approach.

Customer value is at the core of everything we do. Therefore, this role will be responsible for ensuring service quality for existing clients, building strong relationships with new customers, and supporting business development initiatives.

Responsibilities

• Understand and analyze client requirements to design and deliver end-to-end solutions within SAP Transportation Management (TM)
• Configure and implement SAP TM processes, including planning, execution, freight settlement, and charge management
• Integrate SAP TM with adjacent modules such as SAP EWM, Logistics Execution (LE), and S/4HANA Core
• Support and validate transportation scenarios across the logistics landscape, including embedded and decentralized TM setups
• Specify, coordinate, and test enhancements (RICEF objects)
• Collaborate on end-to-end supply chain processes, ensuring seamless integration between transportation and warehouse operations
• Participate in complex consulting projects across management, process, and IT domains, with a strong focus on logistics and supply chain (Automotive experience is a plus)
• Develop and implement innovative logistics and transportation concepts focused on efficiency, cost optimization, and scalability
• Build and maintain long-term client relationships and act as a trusted advisor
• Support pre-sales activities and contribute to new business opportunities

Qualifications

• Bachelor’s or Master’s Degree in Business Administration, Engineering, Supply Chain, or related field
• 7+ years of experience in SAP TM (Transportation Management), including configuration and process design
• Solid understanding of SAP EWM processes and integration with TM
• Experience with embedded TM in S/4HANA is highly desirable
• At least 3 full-cycle SAP implementations, preferably including TM
• Strong knowledge of transportation planning, freight execution, carrier selection, and settlement processes
• Experience with SAP integration points (EWM, LE, GTS, or ERP/S/4HANA)
• SAP TM certification is a strong plus
• Fluency in English (Spanish is a plus)
• Strong analytical, structured, and solution-oriented mindset
• Excellent communication and stakeholder management skills
• Willingness to travel (50%+) if required

Good to know

• Contract type: Unlimited
• Start date: Flexible
• Working time: Full-time
• Consulting experience is a plus

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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.

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