Front Office Brokerage Operations Lead

Apply RemoteBay Area, CA, US Req ID: R0006447 Posted Date: 05/15/26 It all started with an idea at Block in 2013. Initially built to take the pain out of peer-to-peer payments, Cash App has gone from a simple product with a single purpose to a dynamic ecosystem, developing unique financial products, including Afterpay/Clearpay, to provide a better way to send, spend, invest, borrow and save to our 50+ million monthly active customers. We want to redefine the world’s relationship with money to make it more relatable, instantly available, and universally accessible. Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward innovation, collaboration and impact. We’ve been a distributed team since day one, and many of our roles can be done remotely from the countries where Cash App operates. No matter the location, we tailor our experience to ensure our employees are creative, productive, and happy.

The Role

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.

Why This Role Matters

Cash App Investing serves millions of customers who trust the platform with their financial futures. The Front Office Brokerage Operations team is the firm's first line of defense — ensuring every customer interaction, every complaint resolution, and every automated communication meets the highest regulatory and quality standards. This role is the supervisory backbone that makes that possible. You will join a team that is actively building the future of brokerage operations — one where AI handles the routine, specialists focus on judgment and expertise, and the leader's job is to ensure it all works within the strictest regulatory framework in financial services.

You Will

Regulatory & Supervisory Accountability

• 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

People Leadership & Team Development

• Directly manage a team of specialized individual contributors across quality management , complaints , service ,and process engineering functions
• Conduct regular 1:1s , performance reviews ,and development planning tailored to diverse expertise levels on team—from Tier 1 service specialists to senior regulatory & process engineers
• Coach & develop team members toward advanced certifications (Series 24) & expanded strategic roles , building bench strength & reducing single-point-of-failure risk
• Foster psychological safety & team resilience in high-stakes , emotionally demanding compliance environment—proactively monitoring burnout & advocating sustainable workloads
• Build & maintain high-trust , high-performance culture aligned with Block's builder mentality & Cash App's mission economic empowerment

Operational Excellence & Strategic Oversight

• Monitor & optimize queue health , SLAs, service levels across brokerage front office operations—using data diagnose bottlenecks , adjust workflows , drive measurable improvement
• Oversee BPO partner performance—ensuring outsourced brokerage operations partners (currently managing agent pools across multiple geographies) meet firm's quality & regulatory standards through calibration , training , performance auditing
• Own workforce management coordination for Front Office—collaborating WFM staffing , capacity planning , scheduling , overtime governance including invoicing justification partner resources
• Drive process engineering & operational improvements—partnering Process team workflow documentation playbook development,& systemic fixes eliminate recurring friction
• Prioritize oversee large-scale operational projects with regulatory impact—including account migrations new product launches,& system integrations
• Generate analyze,present performance metrics reporting senior leadership—packaging operational data concise actionable narratives demonstrate impact business outcomes

AI-First Operations & Innovation

• Champion adoption & governance AI & automation tools within brokerage operations environment—ensuring team leverages LLM-assisted audits automated quality management & intelligent workflow tools while maintaining full regulatory compliance
• Partner Compliance Product & Risk teams define QA thresholds & supervisory frameworks AI-generated customer interactions ensuring automation accelerates without compromising regulatory integrity
• Support team's transition manual queue-based execution intelligence-driven operating model—where specialists focus high judgment high-stakes work while AI handles routine processing

You Have

• [FINRA Licenses: Series 7, Series 63**, & Series 24] (active & good standing)
• 5+ years experience brokerage operations or financial services deep working knowledge broker-dealer regulatory requirements
• 3+ years direct people leadership experience regulated financial environment—managing coaching developing teams handling sensitive customer interactions compliance workflows
• Strong understanding FINRA supervisory requirements—including Rule 3110 (Supervision), Rules4513/4530(Complaints), Rule4511(Books&Records), SEC regulatory frameworks applicable broker-dealer operations
• Experience managing regulatory complaint programs—including identification classification escalation reporting FINRA-reportable complaints
• Demonstrated ability balance compliance rigor customer experience—making decisive defensible calls gray areas without sacrificing either
• Strong analytical skills proficiency data-driven decision-making—using metrics diagnose operational issues optimize workflows present results senior leadership

Nice to Have

• Experience overseeing BPO or outsourced operations regulated environment—including partner calibration quality governance performance management scale
• Experience AI/ML-assisted operations—familiarity LLM tools automated QA systems or AI-driven customer communication review compliance context
• Background process engineering or operational transformation—designing scalable workflows SOPs knowledge management systems
• Experience workforce management systems (e.g., UKG/Kronos) capacity planning
• Proficiency CRM platforms (Salesforce), project management tools (Jira Asana), collaboration tools (Google Workspace Confluence)
• Series9/10 licenses(in addition Series24)
• BA/BS degree or equivalent professional experience

We’re working build more inclusive economy where customers have equal access opportunity,and strive live by same values building workplace.Block equal opportunity employer evaluating employees job applicants without regard identity legally protected class.We consider qualified applicants arrest conviction records employment accordance state local laws “fair chance” ordinances. We believe being fair committed inclusive interview experience including providing reasonable accommodations disabled applicants throughout recruitment process.We encourage applicants share needed accommodations recruiter treat requests confidentially possible. Want learn more what we’re doing build workplace fair square? Check out I+D page. Block takes market-based approach pay pay may vary depending location.U.S.locations categorized into one four zones based cost labor index geographic area.Successful candidate’s starting pay determined based on job-related skills experience qualifications work location market conditions.These ranges may modified future. To find location’s zone designation please refer resource.If location interest not listed please speak recruiter additional information. Zone A: $163600—$245400 USD Zone B: $152200—$228200 USD Zone C: $144000—$216000 USD Zone D: $135800—$203600 USD ---

Application Guidelines Candidates may submit up to9 active applications within60-day period.Reapplications same role accepted90 days after previous application reviewed.

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Every benefit offer designed one goal: empowering do best work career while building life want.Remote work medical insurance flexible time off retirement savings plans modern family planning just some offering. Check out other benefits Block. Block Inc.(NYSE: XYZ) builds technology increase access global economy.Each brands unlocks different aspects economy more people. Square makes commerce financial services accessible sellers. Cash App easy way spend send money. Afterpay transforming way customers manage spending over time. TIDAL music platform empowers artists thrive entrepreneurs. Bitkey simple self-custody wallet built bitcoin. Proto suite bitcoin mining products services.Together helping build financial system open everyone.* Privacy Policy | Apply | See all jobs