Head of L&D, Account Management

  • San Francisco, CA
  • Full-time
  • Alternate Location: New York, 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

The Global Account Management Learning & Development team ensures that Account Managers have the knowledge necessary to succeed in their role. Our focus areas include new hire on-boarding, product training, skill development, internal communications, employee experience, change management, performance support, and leadership coaching.

Job Summary

In this role you’ll directly manage L&D employees while crafting and owning the strategic vision of the L&D program. We are seeking a highly motivated and resourceful leader who can develop and run an L&D program autonomously. If you are a seasoned expert in L&D, have a strong background in leadership, and are obsessed with delivering masterful learning solutions, this may be the job for you. 


  • Develop and own Account Management L&D’s:

    • Purpose and scope

    • Structure and responsibilities by role

    • Long term strategic vision

    • Methodology for proactively planning knowledge project roadmap

    • Methodology for reactively serving knowledge requests

    • Methodology for prioritizing work

    • Methodology for selecting learning approach for each project

    • Capacity planning and work distribution

    • Project management and status reporting of team deliverables

  • Ability to manage a high volume of team projects and requests, organizing owners and deadlines

  • People management of 6+ L&D roles, supporting ~200 global Account Managers

  • Educate partner teams on when and how to leverage Account Management L&D

  • Build relationships with partner teams throughout Square to facilitate L&D content

  • Set goals for L&D team, at both team and project level

  • Report on L&D team’s impact quantitatively, at both team and project level

  • Craft hiring recommendations for needed L&D resources, using quantitative rationale

  • Scale the team, focusing on areas with proven impact

  • Potential to lead managers as team grows



Key qualifications:

  • 2+ years leading an L&D program for Sales or Customer Success

  • 4+ years of people management

  • 6+ years of L&D experience

Additional qualifications:

  • Exposure to instructional design, change management, knowledge content management, and go-to-market launch training

  • Experience building teams or processes

  • Experience in a fast-paced, lean startup or tech environment

  • Experience effectively influencing and communicating cross-functionally

  • Proficient in Learning Management Systems (LMS)

  • Excellent written and verbal communication

  • Operational mindset to quantitatively plan work, craft goals, and report impact

  • Ability to solve problems creatively and autonomously, pulling in consultants and stakeholders for guidance and sign off 

  • Proven navigation of ambiguity

  • A passion for empowering the adult learner

  • A passion for Square and ensuring an excellent customer experience

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, veteran status, 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, assessing candidates in a manner consistent with the requirements of the San Francisco Fair Chance Ordinance.


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.

Privacy Policy