Front Office Brokerage Operations Lead

Block•Bay Area, CA, United States of America, CA

1d•$135,800 - $245,400•Remote

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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
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
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
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