Training Specialist- Cash App

  • Portland, OR
  • Full-time

Company Description

When we launched the little white reader, we invented mobile, ubiquitous payments and enabled anyone to start, run, and grow a business. Ten years and billions of transactions later we’re reimagining commerce for businesses of all types and sizes—we’re enabling the independent electrician to send invoices, helping the beauty salon pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re working to find new and better ways to help businesses succeed on their own terms—and we’re looking for people like you to help shape tomorrow at Square.

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

This position is located in Portland, OR.

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) 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. 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