Learning & Development Lead, Cash App

  • St. Louis, MO
  • Full-time

Company Description

We believe the economy is better when everyone has access. When everyone has room to grow. No one should be left out because the cost is too great or the technology too complex. We started with a little white credit card reader but haven’t stopped there. We’re empowering the independent electrician to send invoices, setting up the favorite food truck with a delivery option, helping the ice cream shop pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re here to help sellers of all sizes start, run, and grow their business—and helping them grow their business is good business for everyone.

Job Description

Cash App is looking for a Learning and Development Lead to join the Cash Customer Operations team in St. Louis. 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, theyll also have to be scrappy and willing to roll up their sleeves, 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.



  • 5+ years of experience in Learning and Development in a fast-paced, frequently-changing business setting.

  • 2+ years of management experience in a Learning and Development environment is strongly preferred

  • 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

At Square, our purpose is to empower – within and outside of our walls. In order to build the best tools for the businesses and customers we support all over the world, we have to start at home with a workforce as diverse and empowered as our sellers. To this end, we take great care to evaluate all employees and job applicants equally, based on merit, competence, and qualifications. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We encourage candidates from all backgrounds to apply and always consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance. Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us by sending an email to assistance(at)squareup.com. We will treat your request as confidentially as possible. In your email, please include your name and preferred method of contact, and we will respond as soon as possible.