Brokerage Operations Lead

Posted Sep 28

Company Description

It all started with an idea at Square 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 app, bringing a better way to send, spend, invest, and save to our millions of monthly active users. We want to make the world’s relationship with money more relatable, instantly available, and universally accessible. This is our mission, and it’s why working at Cash App means so much more than a job.

Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward creativity, collaboration and impact. We’ve been a distributed team since day one, and we’ve got offices and remote teammates across the globe. Our offices are great, but 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.

Check out our locations, benefits, and more at to learn more!

Job Description

The Cash App Operations team is responsible for building and managing a scalable operating environment for a large-scale and fast growing mobile payment app with multiple, external partners and internal, cross-functional stakeholders. You will be the brokerage operations manager responsible for the critical functions of the broker-dealer for Cash App Investing LLC with over 4.5 million brokerage accounts and climbing. You will focus on identifying and remediating operational issues, directly influencing product development for brokerage tooling systems, and ensuring compliance with all applicable laws and regulations. This role is remote friendly within the continental US with travel expected to visit direct reports, staff and extended cross functional partners. Role reports into the C-level leadership of the broker-dealer.

You will be responsible for:

  • Managing introducing brokerage operations functions for Cash App Investing LLC
  • Managing front, middle, and back office brokerage operations functions, such as but not limited to New Accounts, Customer Onboarding, Market Operations, Reconciliations, Trading / Corrections etc
  • Work closely with broker-dealer leadership including the FINOP and Chief Compliance Officer
  • Partner with product development to ensure that new feature readiness includes backend tooling, processes and operational staffing necessary to properly support successful launches
  • Identify, assess, and prioritize operational needs for tooling, system enhancements etc and collaborate with product and engineering for roadmap consideration and build out
  • Maintaining supervisory authority over introducing brokerage operations functions and ensuring up-to-date desktop procedures and written supervisory procedures (WSPs)
  • Maintain a strong working relationship with our clearing, engineering, product, design and legal teams to improve and scale Cash App Investing products, tools, and systems
  • Monitor and review daily exception reports, and evaluate findings using internal procedures
  • Coach, guide and develop our Front, Middle and Back office leadership team
  • Scale the operations functions of the broker-dealer to ensure operational efficiency through process improvement, tooling build out / enhancement and workforce management. Partner with Office Experience team to influence selection of additional broker dealer branch offices as part of further building out your teams.
  • Oversee the on-going operation of the front office team including handling customer inquiries, maintaining compliance, monitoring and driving team and individual performance, record-keeping and scaling/developing the function.
  • Oversee the on-going operation of the back office team including day to day administrative, operational and vendor relationships, managing customer brokerage accounts, trades and transactions to achieve business goals while meeting regulatory requirements.
  • Review outgoing account transfers and close open positions or request transfer extensions
  • Oversee the accurate processing of corporate actions, resolve trade errors, identify suspense positions, etc
  • Provide oversight of our operational playbook with related policies and procedures
  • Establish new and enhance existing operational performance metrics to increase visibility, productivity and efficiency
  • Interface with carrying/clearing firm to review trade/execution reports, quarterly trade activity, and approve new accounts
  • Manage special projects as needed including assisting with examinations and inquiries for the SEC, FINRA and/or inquiring states


You Have:

  • Licenses: Series 7, 66 (or 63) and 24
  • 7-10 years of brokerage operations experience, including 4 years in a management role
  • Expert-level knowledge of front, middle and/or back office brokerage operations
  • Experience managing and training a front, middle and/or back office operations team
  • Ability to quickly learn proprietary web-based front and back office applications
  • Experience collaborating with Product and Engineering functions to ensure that new feature readiness includes backend tooling, processes and operational staffing necessary to properly support successful launches
  • Appreciation for compliance and adherence to government and industry regulations
  • Prior success implementing and updating Written Supervisory Procedures
  • Excellent verbal and written communication skills
  • Ability to travel up to 25%. Direct reports and your staff are located in Portland while extended investing team members are in San Francisco.

Nice to Have:

  • Series 4
  • Experience working at a fast growth FinTech
  • Experience working with Carrying or Clearing Broker-Dealer
  • Extensive SEC/FINRA regulatory and compliance knowledge
  • Excellent research skills including experience with online search tools
  • Bachelor’s in Finance, Economics, or similar area


Additional Information

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. Square is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

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.

Additionally, we consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.

Square, Inc. (NYSE: SQ) builds tools to empower businesses and individuals to participate in the economy. Sellers use Square to reach buyers online and in person, manage their business, and access financing. Individuals use Cash App to spend, send, store, and invest money. And TIDAL is a global music and entertainment platform that expands Square's purpose of economic empowerment to artists. Square, Inc. has offices in the United States, Canada, Japan, Australia, Ireland, Spain, Norway, and the UK.