Learning and Development Lead, Cash App

  • Portland, OR
  • Full-time

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.

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

Cash App is looking for a Learning and Development Lead to join the Cash Customer Operations team in St. Louis or Portland. Our Learning and Development team exists to provide our Advocates with the knowledge and skills required to be successful in their role, as well as providing opportunities for further career growth and development. Focus areas include new hire training, continued development, internal communications, and on-the-job performance support.

Our ideal candidate has managed and developed a team of Trainers, Facilitators, Program Managers, and/or Instructional Designers, has overseen programs operating at scale (both in person and e-learning), and can think strategically about the creation and delivery of adult learning programs. Initially, they will need the ability to be hands-on with the daily functions of the training team, as the Cash App L&D function is not well-established and is currently a team of two trainers. There is a broad range of opportunities including soft skills development, building product knowledge, workflow efficiency, and targeting behaviors that will have the greatest impact on performance.


You have:

  • 5+ years of experience in creating and implementing a Learning and Development program in a fast-paced, frequently-changing business setting.
  • 2+ years of program and people management experience in a Learning and Development environment
  • A deep understanding of and experience in, performance analysis, training facilitation, and instructional design.
  • Strong public speaking, teaching, and coaching skills with a desire to see others succeed.
  • Experience with eLearning development tools and educational technology, as well as in-person facilitation.
  • An analytical, data-focused mindset with a track record of success in a metrics-driven environment.
  • A willingness to roll up your sleeves and get your hands dirty to understand the problems that face our customers and our team.

Additional Information

Cash App treats all employees and job applicants equally. Every decision is based on merit, qualifications, and talent. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. 

We will consider for employment qualified applicants with criminal histories in a manner consistent with each office’s corresponding state and city guidelines.