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 mi…