Learning & Development Onboarding Specialist, Cash App

  • San Francisco, CA
  • Full-time

Company Description

It all started with an idea at Square in 2013. 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, bringing a better way to send, spend, invest, and save to our millions of monthly active users. We want to make the world’s relationship with money more relatable, instantly available, and universally accessible. This is our mission, and it’s why working at Cash App means so much more than a job.

Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward creativity, collaboration and impact. We’ve been a distributed team since day one, and we’ve got offices and remote teammates across the globe. Our offices are great, but many of our roles can be done remotely from the countries where Cash App operates. No matter the location, we tailor our experience to ensure our employees are creative, productive, and happy.

Check out our locations, benefits, and more at cash.app/careers to learn more!

Job Description

We are seeking a Learning & Development Onboarding Specialist to support our growing team at Cash App. You will be instrumental in managing and implementing onboarding programs and supporting other key strategic learning and onboarding initiatives across the organization with a strong focus on content, operations, and program design.

The ideal candidate is one who is interested in making a significant impact in one of the most valued and visible groups in the company and excels in a fast-paced, high engagement environment with extraordinary desire to innovate. You are deeply passionate about learning and you are excited by the opportunity to support new hire onboarding for a rapidly growing and broadly distributed organization. This role will work closely with others across the organization including leads, HRBPs, HR Operations, IT, and functional learning partners to drive seamless and impactful learning experiences that reinforce our operating principles, drive connection and community, and build key skills for success. You are comfortable working on projects end-to-end, you are a creative and innovative problem solver, and you are excited about learning and the new hire experience. This role reports into our Learning & Development Operations Manager and works cross-functionally across all teams at Cash.

You Will:

  • Design and deliver orientation sessions for incoming new hires including ownership of Cash App Orientation

  • Develop our new hire learning strategies and curriculum in alignment with organization priorities

  • Build compelling and impactful learning journeys for all new hires rooted in Cash culture

  • Leverage facilitation skills to lead high-impact, effective, and engaging learning experiences for new hires, employees and managers. 

  • Lead onboarding experience and new employee development programs from start to finish, partnering cross functionally to execute.

  • Work collaboratively with functional learning leads and key stakeholders across the organization to ensure that on-the-job onboarding is tailored and authentic for disciplines and teams.

  • Build a sense of connection and community for new hires

  • Drive adoption of critical tools to ensure a seamless onboarding experience. Leverage digital learning tools to create impactful learning paths and a holistic, scalable learning experience

  • Track and report on key metrics to measure effectiveness and impact of Cash’s onboarding programs. Collect ongoing feedback to improve learning experiences and programs


  • Minimum of 4 years in learning & development, HR, Operations or related function

  • Passionate about employee engagement and culture

  • Strong facilitation skills and can easily engage an audience

  • Exceptional project management skills and possess both operational rigor and a detail orientation

  • Comfortable with learning technology and on-demand learning to enhance, support and track the onboarding experience

  • Comfortable in a dynamic environment, and can balance setting long-term strategic priorities with high-quality, tactical execution

  • Excellent verbal and written interpersonal skills

  • Utilize qualitative and quantitative data in order to inform and improve programs

  • Experience collaborating across the organization and influence partners to achieve results.

  • Ability to prioritize workload and effectively balance competing priorities in order to meet ambitious deadlines.

  • Strong interpersonal, communication skills and cross-functional collaboration.

  • Comfort dealing with ambiguity.

Additional Information

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Square is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. 

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page

Additionally, we consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.

Square, Inc. (NYSE: SQ) builds tools to empower businesses and individuals to participate in the economy. Sellers use Square to reach buyers online and in person, manage their business, and access financing. Individuals use Cash App to spend, send, store, and invest money. And TIDAL is a global music and entertainment platform that expands Square's purpose of economic empowerment to artists. Square, Inc. has offices in the United States, Canada, Japan, Australia, Ireland, Spain, Norway, and the UK.

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