Learning Specialist Lead, Cash App

  • Portland, OR, USA
  • Full-time
  • Alternate Location: St. Louis, United States
  • Position open to remote: No
  • Current Square Employee?: Apply via go/jobs with your Square email.

Company Description

Cash App is the fastest growing financial brand in the world. Initially 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 app with over 24 million monthly active users. We are bringing a better way to send, spend, invest, and save to anyone who has ever sought an alternative to the traditional banking system.

Loved by customers and pop culture, we’ve consistently held the top spot for finance in the App Store for many years, seeing more engagement with millions of followers across social media in a day than most brands see in a year. We are building an ecosystem to redefine the world’s relationship with money by making it universally accessible.

We want to hire the best talent regardless of location. Our employment model is distributed, offering the opportunity to collaborate with teams across the world in San Francisco, New York, St. Louis, Portland, Toronto, Kitchener-Waterloo, Sydney, and Melbourne.

Interested in learning more?

Job Description

Cash App is looking for a Learning and Development Lead to join the Cash Customer Operations team.  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, continuing education, professional development and on the job performance support.

Our ideal candidate has managed and developed a team of Learning Specialists, 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’ll also have to be adaptable and flexible, willing to roll up their sleeves and take risks as we introduce this role into the L&D ecosystem.  A broad range of coachable opportunities exist including soft skills development, building product knowledge, workflow efficiency, and targeting behaviors that will have the greatest impact on performance and business outcomes. 


You will:

  • Manage a team of Learning Specialists and/or Instructional Designers to meet/exceed performance expectations.
  • Assess Learning Specialist competencies and talents, identify ongoing performance improvement opportunities and create individualized development plans to drive skill mastery.

  • Measure the impact of the Learning Specialists and the programs they deliver through ongoing  data analysis. 

  • Ensure strategic alignment between L&D and Cash App organizational goals. 

  • Target performance improvement opportunities identified through observational feedback, data analysis and stakeholder collaboration.

  • Optimize the learner experience by developing the soft skills and technical knowledge of Learning Specialists. 

  • Identify learning needs by consulting with stakeholders and conducting needs assessments. 

  • Design and facilitate programs that increase the level of product and technical knowledge across the team. 

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


  • 4+ years of experience in a Learning and Development role in a fast-paced setting.

  • 2+ years of management experience (Learning and Development environment is strongly preferred).

  • A deep understanding of and experience with virtual and classroom-based facilitation techniques and coaching methodologies.

  • Prior work developing and implementing training solutions that improve employee efficiency.

  • Exceptional team building, leadership and organization skills.

  • A proven track record of analyzing performance and successfully coaching a team to attain elevated performance goals.

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

  • An ability to shift on the fly, work within a highly ambiguous environment and perform at a high level with minimal direction.

  • Ability to travel up to 30% of the time.

Nice to Have:

  • Experience with eLearning development tools and educational technology/platforms.

  • Familiarity with Learning Management System (LMS) functions and capabilities

  • Project/Program Management experience.

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 local guidelines.