Head of Learning

  • San Francisco, CA
  • Employees can work remotely
  • Full-time
  • Alternate Location: New York, United States
  • Position open to remote: Yes
  • Current Square Employee?: Apply via go/jobs with your Square email.

Company Description

Square builds common business tools in unconventional ways so more people can start, run, and grow their businesses. When Square started, it was difficult and expensive (or just plain impossible) for some businesses to take credit cards. Square made credit card payments possible for all by turning a mobile phone into a credit card reader. Since then Square has been building an entire business toolkit of both hardware and software products including Square Capital, Square Terminal, Square Payroll, and more. 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

We're looking for a Head of Learning to guide leadership and L&D initiatives for Square. You are interested in making a significant impact on one of the most essential teams in driving Square's People strategy and vision. You will excel in a fast-paced, high engagement environment with an extraordinary desire to innovate. You will help promote awareness, understanding, acceptance, delivery, and successful adoption of learning programs that guide overall employee engagement. You're comfortable speaking up and driving programs forward despite any unexpected roadblocks and working with employees at all levels across Square.

This role can be located anywhere within the US, and can be fully remote.

You will:

  • Establish plans, priorities, and a roadmap for the Learning team to create behavior change and growth at a corporate level and consult/support team needs with best practices, content, and resources
  • Work with HR Business Partners and others across foundational teams to assess organizational learning needs and provide talent development strategies that address performance gaps
  • Support our growth by designing, scoping, and sequencing our learning programs to support leadership, employees, and team effectiveness globally
  • Work with partners to design and deliver a leadership development program customized to our defined leadership competencies at Square
  • Lead our on-boarding experience from offer acceptance to the first year on the job: develop, monitor, and evaluate practices aligned with Square's operating principles
  • Guide the Learning team's approach to learning management technology, information sharing systems, and training delivery as we continue to scale and become more decentralized and geographically distributed
  • Select and work with outside vendors and consultants that further raise our game
  • Measure training effectiveness and impact of communications and change management programs




You have:

  • 8+ years' experience in increasingly responsible business roles, including Human Resources, Talent Management, and/or related positions
  • Experience designing, developing, implementing, and evaluating learning and leadership programs with skills in assessing and measuring effectiveness
  • Process and project management, with the ability to manage multiple projects and priorities concurrently
  • The ability to negotiate and communicate with a variety of stakeholders and influence senior leaders
  • Experience developing and maintaining internal and external interpersonal business relationships with HR Business Partners and other key stakeholders at all levels
  • Successful team building and team leadership experience
  • Budgeting, forecasting, and providing clear and concise analyses of learning programs and investments
  • The ability to operate both independently and as part of a collaborative global team
  • Experience designing and developing virtual learning solutions
  • Bachelor's degree; Masters in Education, OD, or similar discipline preferred


Additional Information

At Square, we value diversity and always treat all employees and job applicants based on merit, qualifications, competence, 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 the requirements of 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)squareup.com. 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.


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