Training Specialist, Cash App

  • St. Louis, MO
  • 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

In this role, you will be primarily focused on facilitating new hire training and supporting learning and development opportunities that drive performance improvement across the Cash App Customer Success team. As a Training Specialist, you’ll be setting up new Customer Success Advocates for success by facilitating and managing the logistics of new hire training, coaching new hires through their first 3 months on the job, constantly iterating on current training programs to drive improvement, and working closely with other teams and leaders on a variety of development projects.

The Cash App L&D team is small and mighty: you will be spending 70% of your time planning, optimizing and delivering new hire training programs and the remaining on other learning and development tasks such as content development, upskilling tenured employees, tracking results, etc. Your role involves collaborating closely with the Customer Success Leads and other cross-functional teams.

The ideal candidate is a self-motivated team player with a strong sense of ownership and a "get things done" attitude. You’re effective at managing multiple projects at once, very detail-oriented and organized, like to be busy and productive, learn quickly, and have a track record of being adaptable in a fluid, high-growth environment.

You Will:

  • Deliver new hire training to Cash App and Business Partner Advocates

  • Provide real time coaching to Advocates to improve performance and shorten ramp up timelines

  • Create, update and curate training content as needed

  • Organize and arrange all back end logistics associated with the new hire training program

  • Provide qualitative and quantitative feedback to Customer Success Leaders regarding new hire performance

  • Engage shared service partners as needed to deliver select training modules (Quality Assurance, Risk Operations, etc.)

  • Project manage select L&D initiatives projects so they are delivered on-time and within scope

  • Contribute to L&D projects by doing research around best practices 

  • Support content development, content design, and facilitate L&D course offerings when needed



  • BA/ BS degree or 2+ years practical experience in a Learning and Development role

  • 2+ years managing organizational projects and programs

  • Exceptional presentation skills 

  • Strong interpersonal and written/verbal communication skills 

  • Experience consulting with business leaders/stakeholders

  • Ability to be flexible, adaptable and solutions-oriented in the face of problems

  • Passion for trying, learning, improving, and sharing best practices

  • Proactive team member with excellent attention to detail and follow through; Strong sense of urgency to drive projects to completion

  • Ability to balance competing priorities in a fast-paced environment, and push back on stakeholders when necessary

  • Understanding of Adult Learning Theory

Even Better:

  • A degree in adult learning, organizational development, organizational behavior, industrial-organizational psychology, human resources, or equivalent

  • Virtual facilitation experience

  • Instructional Design experience

  • Insight into project management, stakeholder management and results tracking methods

  • Exposure to Learning Management Systems


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.