Head of Sales Enablement and Productivity

  • San Francisco, MO
  • Employees can work remotely
  • Full-time
  • Alternate Location: Atlanta, United States

Company Description

Since we first opened our doors in 2009, the world of commerce has evolved immensely – and so has Square. After enabling anyone to take a payment and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, run a busy kitchen, book appointments, engage loyal buyers, and hire and pay staff. And across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow all in one place.

Today, we’re a partner to sellers of all sizes – large, enterprise-scale businesses with complex commerce operations, sellers just starting out, as well as merchants who began selling with Square and have grown larger over time. As our sellers scale, so do our solutions. We all grow together.

There is a massive opportunity in front of us. We’re building a business that is big, meaningful, and lasting. And we are helping sellers around the world do the same.

Job Description

Square Sales is seeking a leader for our Global Sales Enablement & Productivity function. This team exists to help our Sales team serve our customers better while growing their sales attainment. This service involves optimizing three major workstreams; 1) training (both leading and enabling others in the org who train); 2) coaching (developing the frameworks, launching them, and working with sales leadership to build accountability governance); and 3) sales content and collateral (making sure Sales has the right resources to engage and win more customers). We are judged on our ability to help salespeople gain the knowledge and skill to do their job to satisfaction in collaboration with sales leadership. 

You will:

  • Manage a team of program managers, instructional designers, content creators, and trainers as you build the integrated roadmap of our enablement programs (onboarding, sales rep competencies, leadership development, go-to-market content, knowledge management, and learning experience design).

  • Evangelize the function by determining and communicating success metrics for each program (in partnership with our Strategy & Operations team) and adjusting the roadmap in response to our measurement.

  • Iterate on this roadmap as you partner with Sales Leadership to understand the organization’s greatest learning & development needs. 

  • Partner with our Product teams to create a bidirectional flow of information (where Product delivers new content to salespeople in advance of feature launches, and Sales delivers customer feedback to influence our product roadmap).


You Have:

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

  • Demonstrated success when leading a multidisciplinary organization of L&D workstreams (and managing professionals across these disciplines). 

  • Measurement experience for articulating the impact of an L&D program on a Sales organization’s performance.

  • A history of facilitating learning experiences through a variety of platforms (in-person / virtual lectures, experiential learning, asynchronous / on-demand).

  • Strong business partnering skills to understand & synthesize the needs of a global, ecosystem Sales org and how various L&D approaches can move the needle.

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

  • Familiarity with a variety of tools designed for Sales performance and feedback, such as Salesforce, Salesloft, Gong, Guru, Docebo, and Articulate.

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.


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

Block, Inc. (NYSE: SQ) is a global technology company with a focus on financial services. Made up of Square, Cash App, Spiral, TIDAL, and TBD54566975, we build tools to help more people access the economy. Square helps sellers run and grow their businesses with its integrated ecosystem of commerce solutions, business software, and banking services. With Cash App, anyone can easily send, spend, or invest their money in stocks or Bitcoin. Spiral (formerly Square Crypto) builds and funds free, open-source Bitcoin projects. Artists use TIDAL to help them succeed as entrepreneurs and connect more deeply with fans. TBD54566975 is building an open developer platform to make it easier to access Bitcoin and other blockchain technologies without having to go through an institution.

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