Senior Program Manager and Facilitator, Leadership

  • San Francisco, CA
  • Full-time

Company Description

We believe the economy is better when everyone has access. When everyone has room to grow. No one should be left out because the cost is too great or the technology too complex. We started with a little white credit card reader but haven’t stopped there. We’re empowering the independent electrician to send invoices, setting up the favorite food truck with a delivery option, helping the ice cream shop pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re here to help sellers of all sizes start, run, and grow their business—and helping them grow their business is good business for everyone.

Job Description

You will:

  • Create a leadership curriculum ranging across the entire leader lifespan (newly promoted, tenured, managers  and managers, etc) that reinforces our operating principles and drives a culture of inclusion and belonging.

  • Design leadership programs and resources ranging from online learning materials to multi-day leadership and/or skill development workshops

  • Facilitate programmatic and custom design learning programs with excellent facilitator ratings

  • Assess individual, team and organizational learning needs, and develop impactful and scalable learning opportunities

  • Partner with HRBPs, senior leaders, and functional training leads to define 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 initiatives (in person, out of the classroom, or online) and processes based on learning strategies

  • Support the creation of standardized metrics and evaluation processes across learning programs to ensure data driven approach when evaluating and addressing learning needs

  • Ensure materials are up to date and relevant to ensure a seamless experience for learners (e.g., course outline, presentation materials, handouts, communications, guides, etc.)

  • Utilize the LMS to store course curriculum, capture program registration, and run reports on attendee completion status

  • Select and curate relevant leadership content for self directed global consumption.

  • Support a peer to peer program by training key leaders to facilitate sessions


You have:

  • Bachelor's Degree or equivalent practical experience

  • 7+ years of work experience in a related field (Learning & Development, Talent Management, Leadership Development)


Preferred qualifications:

  • 5+ years developing and leading training efforts with direct experience creating learning programs and facilitating leadership workshops

  • Demonstrated ability to build trusted relationships across diverse range of stakeholders and to work across boundaries to build infrastructure

  • Thrive in a fast-paced environment with a passion for solving problems while being resourceful

  • Excellent interpersonal skills, including written and verbal communication skills

  • Excellent organizational capabilities

  • Coaching certification a plus

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.