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Cash App Logo Cash App · Finance

Front Office Brokerage Operations Lead

United States, Bay Area Employment contract 135800.00 - 245400.00 USD / Year · Job Posted May 16, 2026
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Job 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.

Job Responsibility

  • Regulatory & Supervisory Accountability
  • People Leadership & Team Development
  • Operational Excellence & Strategic Oversight
  • AI-First Operations & Innovation

Requirements

  • 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
  • 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

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

What we offer

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