Learning & Development Program Manager, Cash App Operations

  • 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

What does the Learning & Development team do? We’re here to help Customer Success Advocates and Risk Ops Specialists start, run, and grow! The Customer Success Learning & Development team ensures that our team members are equipped with the knowledge and skills they need in order to be successful in their role, as well as provide opportunities for further career growth and development. Our focus areas include: new hire on-boarding, continued development, internal communications, and on-the-job performance support. 

In this role, you will be focused on designing, delivering, and measuring the impact of the new hire learning and development programs which drive performance improvement across the Customer Operations team. There is a broad range of opportunities in developing new hire training content including, how to build product knowledge, create workflow efficiency, develop soft skills for customer interactions, introduce newbies to our company, culture and team, and how to instill and encourage the behaviors that will have the greatest impact on performance. This is a huge opportunity for the right individual to make an enormous impact in an exciting, diverse environment. 

This role might be for you if... 

You dream big and you’re eager to explore new opportunities and get things done. You value relationships and know how to collaborate and communicate effectively with others at any level. You can thrive in complexity and can successfully oversee multiple projects in a fast-paced environment while staying focused on key priorities. You are trusted for the speed and quality of your decision-making. You have a firm understanding of adult learning theory and extraordinary facilitation & presentation skills.

This position is located in St. Louis, MO. 

What you’ll do: 

● Design, develop, lead, and implement innovative new hire learning and development strategies and effective new hire learning curriculum 

● Guide the organization in prioritizing and developing end-to-end new hire onboarding strategy and curricula with available resources, in coordination with stakeholders, and aligning with organizational strategic priorities 

● Utilize data to monitor and analyze the effectiveness of new hire learning and development programs; support a culture of continuous development within the Learning & Development Team 

● Provide input and outcome data on learning impact and recruitment recommendations regularly in reports to management and partners 

● Lead the development of training programs for Cash App people managers, Customer Success Advocates and Risk Specialists 

● Develop relationships with key stakeholders to ensure that learning and development initiatives are aligned with both individual and team needs 

● Develop and support training solutions and processes that improve the workflow and efficiency of Cash App Advocates and build their skills as new hires step by step 

● Enable operational changes that drive efficiency and organizational effectiveness and iterate based on new hire and organizational qualitative and quantitative feedback 

● Partner with other members of the L&D team to deliver cross-functional training programs. 


● 4+ years of experience in Learning and Development in an intensely scaling technical business setting. 

● 2+ years of Program Management Experience

● A deep understanding of and experience in instructional design, performance analysis, performance coaching and facilitation. 

● Strong public speaking, teaching, and coaching skills with a desire to see others succeed. 

● Experience with e-learning development tools such as Storyline and Captivate and familiarity with an LMS.  

● An analytical, data-focused mindset with a track record of success in a metrics-driven environment. 

● A proven track record of building, maintaining and managing large-scale training programs. 

● Experience with change management fundamentals and learning/educational technology

● An end-to-end problem solving skill-set, from structuring a complex problem through to developing actionable recommendations and working with other teams to get solutions implemented.

● A willingness to roll up your sleeves and get your hands dirty in order to understand the problems that face our customers and our team. 

● A proactive nature, a sense of urgency, and a high degree of self-motivation to go above and beyond to meet the needs of our team.

● People management experience preferred 

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. Perks At Square, we want you to be well and thrive. Our global benefits package includes: Healthcare coverage, Retirement Plans, Employee Stock Purchase Program, Meal reimbursements, Wellness perks, Paid parental leave, Flexible time off, Learning and Development resources