Posted On: 7-21-2021
Position Title: Learning and Development Lead
Job Location: Atlanta, GA or Philadelphia, PA
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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, Customer Operations team is looking for a Learning and Development Lead to support our Cash Customer Operations team (CCO). The L&D Lead is responsible for leading a team of learning professionals that include learning specialists, program managers, instructional designers and operations managers. They’re also responsible for creating the strategy that will guide learning, training and development programs across multiple sites and disciplines. This is an opportunity to further shape our learning culture into one that ensures that learning is embedded across functions, roles and geographies. The L&D Lead will shape and drive best-in-class learning journeys and talent development to support all levels of training and development opportunities.


What We Do.

  • We ensure that learning and development are embedded in all areas of the CCO organization: training, talent development, leadership development, continual learning, and career pathing. We’re responsible for designing the systems, processes, and capabilities within the organization to drive learning programs, in support of our strategy and growth plans.
  • We define how we create, curate, and deliver development experiences and learning paths and implement these experiences in alignment with the Cash learning culture
  • We design curriculum, facilitate training courses, and provide the tools to advance the careers of Cash Customer Operations employees.
  • We consult and provide strategic direction with internal stakeholders to assess needs and activate training courses, recommend external options, or develop specific L&D initiatives where appropriate.


Is This You?

Our ideal candidate has managed and developed a diverse 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. There is a broad range of opportunities including soft skills development, building and maintaining product knowledge, workflow efficiency, and targeting behaviors that will have the greatest impact on performance. This is a cross-functional role that relies heavily on input from a diverse group of stakeholders and requires interpersonal savvy, strong prioritization and the ability to navigate aligned but competing priorities.


You will:

  • Design & share a vision and strategy. You have a vision. It’s informed and guided by the mission of Cash and it’s pushed forward by the team you’ve developed, motivated and inspired – this is what it takes to lead L&D for CCO. You’re a subject matter expert ready to build and implement a comprehensive L&D strategy that will support the scale of the business and the growth of all employees as they strive to reach their full potential in a variety of roles throughout CCO. You’re committed to sharing the L&D strategy and its relationship to the Cash mission broadly to ensure that all stakeholders are aligned.
  • Lead and inspire. This team is growing in size and scope. The L&D Lead will be responsible for supporting and developing a team of seasoned L&D professionals and ensuring our teams stay informed, well-versed and knowledgeable on new content, processes/procedures, tools and industry best-practices.
  • Develop strong relationships and partnerships. Strong cross-functional partnership is a hallmark of CCO’s L&D Lead.The L&D Lead partners with internal and external teams to understand business objectives and also, specific or individual team needs and consistently translate and prioritize into the training and/or learning roadmap. You’ll build strong relationships across functions and geographies to ensure that L&D deliverables are aligned with CCO and business-specific needs.
  • Guide us toward the best L&D tools and technology. The L&D Lead will demonstrate knowledge and application of cutting-edge, nimble, just-in-time tools.
  • Gather great data and insights and then, act. Connect with key stakeholders and business teams to understand business changes that will influence the design and/or future changes within L&D programs such as new hire training, continuing education, and professional development; conduct regular needs analyses that will help determine prioritization of work and ensure alignment with the organization’s strategic goals; foster partnership with HR in the development and implementation of talent assessment, career development and coaching for all levels of the CCO organization. Evaluate skill sets and gaps based on level, role and discipline; provide data-driven presentations to the business that track and evaluate program effectiveness for improvement plans and; develop a feedback program to drive and capture key insights from business leaders throughout CCO. 


  • 5+ years of senior leadership 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
  • Takes an entrepreneurial approach and continuously innovates to achieve great results.
  • A passion for the entire people process; fosters connection by putting people first and building trusting relationships.
  • Capable of effectively managing multiple demands from a variety of sources.
  • 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. 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