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,...