Chief Operating Officer, Cash App Investing LLC

  • San Francisco, CA, USA
  • Full-time
  • Current Square Employee?: Apply via go/jobs

Company Description

Cash App is the fastest growing financial brand in the world. 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 money app with over 15 million active monthly users (as of 4Q18). Loved by customers and by pop culture, we’ve held the #1 spot in finance on the App Store for almost two years, and our social media posts see more engagement in a day than most financial brands see in a year. With major offices in San Francisco, New York, St. Louis, Portland, Kitchener-Waterloo, and Melbourne, Cash App is bringing a better way to send, spend, and save to anyone who has ever sought an alternative to today’s banking system.


Job Description

We've recently introduced Cash App Investing and now you can instantly buy stock in your favorite companies with as little as $1 using our free fractional trading feature! We're looking for a world class leader to be the face of our broker-dealer subsidiary, Cash App Investing LLC. The ideal candidate for this role is someone who has deep experience in financial services including operating an introducing or carrying broker dealer.  This executive will be an experienced, polished, admirable and agile professional that can balance operating a regulatorily compliant business with power charging the investment arm of the fastest growing, mobile consumer financial application. You will be well versed in operating a broker dealer from inside to out with the chops to continue building a world class team.


  • Program Owner: We are looking for this executive level hire to own, manage & monitor the Cash App Investing program in close partnership with the CEO

  • Performance Manager: Design, implement & monitor KPIs for Cash App Investing 

  • Business Support: Support our business by providing oversight, guidance & challenge in the identification of risk, management & monitoring of day-to-day trading activities 

  • Monitors & Escalates: Drives resolution of significant broker-dealer issues, escalating, and providing reporting to senior management as needed

  • Training, Communication & Knowledge Exchange: Develop & maintain broker-dealer training curriculum 

  • Operations Management - Oversight of all brokerage operations and key performance metrics/operational efficiency including trading, account support and management and financial operations etc.  Maintain essential internal relationships with our Cash App cross functional partners including: 

    • Cash App Investing: Ensure overall integrity of trading system, monitoring key order metrics, and remediating issues or needed enhancements as identified. 

    • Cash App Leadership: Escalate to & report significant broker-dealer issues; inform of new & emerging compliance risks; understand changes to overall broker dealer strategy & budgets  

    • Cash App Compliance: Inform of possible issues as appropriate & engage as needed for regulatory advice on brokerage matters. 

    • Cash App Investing Staff: Engage for reporting on management KPIs & issues requiring escalation to appropriate internal stakeholders  

    • Cash App Financial Operations:  Oversight of monthly net capital computations and functions performed by the Financial Operations Principal (FinOp) including net capital sufficiency, operations funding, and reviewing events which may impact net capital going forward.

    • Square Finance and Strategy:  Meet with designated Square Finance & Strategy (F&S) representatives to review the Investing financial model of the Investing Product and expenditure that will affect Cash App Investing Utilizing the F&S Investing financial model to ensure the firm has sufficient funding to meet expected future obligations and capital requirements based on anticipated expenditure Meeting periodically with Square F&S, Accounting and the firm’s FinOp and President to collectively discuss the capital requirements Filing of annual financial audit with the SEC within 60 days of the end of the financial year Filing of SIPC forms semi-annually and payment of SIPC fees

  • Partner Management:  Maintain and manage all external partner relationships and related commercial agreements including clearing broker, venues, market exchanges and data service providers.  Sourcing and initial diligence of vendors. Perform annual due-diligence reviews of partners including an annual onsite review of carrying / clearing broker

  • Annual Certification:  Establish, maintain, review, test and modify policies and procedures designed to achieve compliance with applicable securities laws and regulations and FINRA rules evidenced in a 3120 report


You have:

  • 15+ years of experience in financial services including experience leading a retail, introducing or carrying brokerage required 

  • FINRA Licenses: Series 24, Series 63 and Series 7 required. Series 65 / 66 preferred

  • Management of key operational teams within a broker-dealer environment including Account Support, Trade Processing, Financial Operations and Supervision/Oversight

  • SEC/FINRA regulatory knowledge and reporting requirements.  Well versed and experienced with FINRA regulators and related examinations, engagements, on-sites and reviews

  • Well experienced in working closely with a broker dealer’s Financial Operations (FinOp) lead and Compliance Officer (CCO) in support of firm operations

  • Familiar with a broker dealer’s annual certification under FINRA Rule 3130

  • Someone who thrives in a highly collaborative and fast-paced environment.

  • Experience operating a registered investment advisory (RIA) a plus, but not required

  • Effective verbal and written communication skills

  • A passion for our mission of economic empowerment through serving the underserved


Additional Information

All your information will be kept confidential according to EEO guidelines.