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

• Drive network reliability by leading the team with a hands-on, technically grounded approach • Deliver a consistently high standard of customer service– responsive, accountable, and solutions-oriented • Support facility maintenance in coordination with the Facilities Team, following standardized procedures and proactive issue-reporting culture • Execute and continuously improve team workflows and SOPs • Apply technical knowledge of the EVSE hardware and software landscape to act as the “subject matter expert” to diagnose and resolve escalated issues • Serve as the primary point of escalation for the 24/7 Network Ops team • Facilitate communications to EVSE and infrastructure vendors when needed • Respond quickly and effectively to issues impacting site and network performance • Track and report performance metrics for the network of deployed assets • Collaborate with Site Operations team members to satisfy SLAs and maintain 99.9% uptime

• Monitor and manage high-volume shared inboxes, triaging and prioritizing inbound inquiries accurately and efficiently • Process license key update requests and migrations for SonarQube Server customers • Handle billing and payment inquiries for Online SonarQube Cloud customers, including payment failures, refunds, cancellations. • Support internal teams with license key requests • Collaborate with Sales and Renewals teams to capture, verify, and track purchase orders through to correct processing • Collect and share customer vendor/procurement forms, ensuring Deal Desk and Finance have complete, accurate information to progress deals • Partner with Sales Operations to ensure inbound leads are correctly captured, enriched, and routed into the CRM • Identify and prioritize commercial inquiries from customers and partners, routing them to the appropriate sales team members • Work cross-functionally with internal teams on communications for special projects, including marketing initiatives, product announcements, and system changes • Proactively flag recurring issues, edge cases, and process gaps to relevant teams to improve tools, routing rules, and overall customer experience • Use the CRM and internal resources to match customer records, review case history, and take appropriate action

• Provide day-to-day IT support for employees across hardware, software, accounts, and access-related issues • Assist with employee onboarding and offboarding, including laptop setup, account provisioning, and equipment management • Troubleshoot basic network, system, printer, conferencing, and office technology issues • Coordinate with internal teams and external vendors on IT-related requests and maintenance • Help manage inventory of laptops, accessories, and office IT equipment • Support company tools and platforms such as Google Workspace, Slack, Zoom, Okta, and related systems • Assist with documenting IT processes, setup guides, and internal procedures • Provide general operational support for office and cross-functional team needs when required