Front Office Brokerage Operations Lead

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 the diverse expertise levels on the team — from Tier 1 service specialists to senior regulatory and process engineers
• Coach and develop team members toward advanced certifications (Series 24) and expanded strategic roles, building bench strength and reducing single-point-of-failure risk
• Foster psychological safety and team resilience in a high-stakes, emotionally demanding compliance environment — proactively monitoring for burnout and advocating for sustainable workloads
• Build and maintain a high-trust, high-performance culture aligned with Block's builder mentality and Cash App's mission of economic empowerment

Operational Excellence & Strategic Oversight

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

AI-First Operations & Innovation

• Champion the adoption and governance of AI and automation tools within the brokerage operations environment — ensuring the team leverages LLM-assisted audits, automated quality management, and intelligent workflow tools while maintaining full regulatory compliance
• Partner with Compliance, Product, and Risk teams to define QA thresholds and supervisory frameworks for AI-generated customer interactions, ensuring automation accelerates without compromising regulatory integrity

Support the team's transition from manual, queue-based execution to an intelligence-driven operating model — where specialists focus on high-judgment, high-stakes work while AI handles routine processing

You Have

• [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

Nice to Have

• Experience overseeing BPO or outsourced operations in a regulated environment — including partner calibration, quality governance, and performance management at scale
• Experience with AI/ML-assisted operations — familiarity with LLM tools, automated QA systems, or AI-driven customer communication review in a compliance context
• Background in process engineering or operational transformation — designing scalable workflows, SOPs, and knowledge management systems
• Experience with workforce management systems (e.g., UKG/Kronos) and capacity planning
• Proficiency with CRM platforms (Salesforce), project management tools (Jira, Asana), and collaboration tools (Google Workspace, Confluence)
• Series 9/10 licenses (in addition to Series 24)
• BA/BS degree or equivalent professional experience

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.