Leadership Program Manager and Facilitator

  • New York, NY, USA
  • Employees can work remotely
  • Full-time
  • Position open to remote: Yes

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

This job can be located in either New York, NY, Toronto or remote

The Leadership Program Manager and Facilitator will oversee the design, content development, and delivery of the leadership curriculum for managers. You will be a part of the Learning & Programs team, and will report to the Leadership Development Lead who is recruiting its first addition to a newly created pod focused on developing leaders across the company. Your role involves delivering an existing curriculum and collaborating with the HR Business Partners, the Inclusion & Diversity team, and other cross-functional teams to answer leadership needs.

You will: 

  • Provide leadership curriculum to new and tenured managers that reinforces our operating principles and inspires a culture of inclusion and belonging.
  • Create leadership programs and resources ranging from online learning materials to virtual development workshops
  • Promote programmatic and custom design learning programs with excellent facilitator ratings
  • Foster and grow a learning community of leaders, allowing them to share experiences, discuss challenges, and network outside their function
  • Support a “train the trainer” program by training essential leaders to facilitate sessions
  • Partner with other Learning & Programs team members, HRBPs, and functional training leads to determine learning needs and address with appropriate learning strategies
  • Build trust with leaders across the organization to foster a leader-influenced approach to learning and development
  • Run end-to-end program management of learning & development programs (before, during, and after the event) based on learning strategies
  • Ensure a data-driven approach to addressing needs by creating metrics and evaluation processes across the leadership curriculum Select and curate relevant leadership content for global use.



Minimum qualifications:

  • Bachelor's Degree or equivalent practical experience
  • 7+ years of work experience in a related field (Learning & Development, Talent Management, Leadership Development)

Preferred qualifications:

  • 3+ years developing and leading training efforts, with direct experience creating learning programs and facilitating leadership workshops
  • Strong content development experience and a deep understanding of learning methodologies
  • Thrive in a fast-paced environment with a passion for solving problems creatively and resourcefully
  • Excellent interpersonal skills, including written and verbal communication skills
  • Excellent prioritization and time management skills

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
  • Flexible time off
  • Learning and Development resources