Head of Sales Enablement and Productivity

  • 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 oversee and grow our Sales Productivity function, which identifies our salespeople’s greatest learning & development needs and provides high-quality content to them in multiple mediums. This team is also responsible for tracking the progress of our salespeople against learning journeys and measuring the impact of our L&D efforts on the effectiveness of the Sales organization.

You will:

  • Manage a team of trainers, curriculum designers, and program managers as you build an enablement roadmap across complementary subjects (onboarding, sales rep foundational skills, selling to ideal customer profiles, new product launches, manager development)

  • Partner with Sales Leadership to enhance our salespeople’s skills and careers as we create revenue for Square. You will also partner with our Product teams to build new content in consideration of product releases/enhancements and funnel Sales feedback to determine our product roadmap.

  • Report to Lead for Sales Operations, Productivity, and Strategy (SOPS).


You Have:

  • 7+ years of experience creating and implementing a Learning and Development program in a frequently-changing business setting

  • 2+ years of program and people management experience in a Learning and Development environment

  • A deep understanding of curriculum and instructional design for Sales organizations

  • Analytical experience measuring the performance of a revenue generating team and the impact of a L&D program on that performance

  • A history of delivering training curriculum in a large class-style setting (50+ individuals), and training/coaching team members as they deliver curriculum

  • Strong business partnering skills, understanding an executive’s needs and blending them with a data-driven approach to create a comprehensive L&D approach

  • A collaborative approach to incorporate Product & Marketing knowledge into the enablement journey

  • Familiarity with eLearning development tools and educational technology, and in-person facilitation

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)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. 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