Front Office Brokerage Operations Lead

Role Description

The Front Office Brokerage Operations Lead is the dedicated frontline manager and Series 24 registered principal for Cash App Investing's Front Office team. This role carries direct FINRA-mandated supervisory authority over the people, processes, and high-exposure workflows of the brokerage operations environment.

You will lead a team of specialized individual contributors spanning quality management, regulatory complaints, customer service, process engineering, and BPO partner oversight. The team operates at the intersection of financial regulation, customer experience, and AI-driven automation — building intelligent systems that protect the firm while delivering an exceptional investing experience to millions of Cash App customers.

This is not a standard operations management role. You will serve as the supervisor-of-record for registered personnel, the final sign-off authority for regulatory workflows, and the operational leader responsible for rebuilding and scaling a high-performing team within a broker-dealer environment undergoing rapid transformation.

Qualifications

• FINRA Licenses: Series 7, 63, and Series 24 (active and in good standing)
• 5+ years of experience in brokerage operations or financial services, with deep working knowledge of broker-dealer regulatory requirements
• 3+ years of direct people leadership experience in a regulated financial environment — managing, coaching, and developing teams handling sensitive customer interactions and compliance workflows
• Strong understanding of FINRA supervisory requirements — including Rule 3110 (Supervision), Rules 4513/4530 (Complaints), Rule 4511 (Books & Records), and SEC regulatory frameworks applicable to broker-dealer operations
• Experience managing regulatory complaint programs — including identification, classification, escalation, and reporting of FINRA-reportable complaints
• Demonstrated ability to balance compliance rigor with customer experience — making decisive, defensible calls in gray areas without sacrificing either
• Strong analytical skills with proficiency in data-driven decision-making — using metrics to diagnose operational issues, optimize workflows, and present results to senior leadership

Requirements

• Serve as the designated Series 24 supervisory principal under FINRA Rule 3110, providing people and process supervision for all registered Front Office personnel
• Own supervisory governance of the FINRA complaints program (Rules 4513 / 4530) — ensuring timely identification, classification, and reporting of FINRA-reportable complaints, including mandated monthly regulatory reporting to Global Complaints
• Provide Series 24 sign-off authority for the Books & Records FINRA Attestation (Rule 4511 / SEC Rule 17a-4), ensuring all required records are maintained, accessible, and audit-ready
• Oversee AI-generated brokerage communications to satisfy FINRA's "human in the loop" supervisory requirement — reviewing and approving LLM-generated customer-facing content before it reaches customers
• Maintain supervisory authority over remediation and target resolve protocols — validating data loads, customer communications, and regulatory disclosures for account adjustments and error corrections
• Ensure regulatory communications and disclosures meet FINRA guidelines across all customer-facing touchpoints, including product migrations, new product launches, and disclosure library updates in coordination with Legal Counsel
• Supervise high-exposure Tier 2 escalation workflows — Account Takeovers (ATOs), identity theft investigations, deceased account settlements, and Power of Attorney validations

Benefits

• Remote work options
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning