Learning & Development Strategist at Square (Remote)

| Atlanta, GA | Remote
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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

What does L&D do?

We're here to help Customer Success learn and grow! The Customer Success Learning & Development team ensures that the Customer Success Org is equipped with the knowledge they need in order to be successful in their role, as well as provide opportunities for further career growth and development. Our focus areas include new hire training, continued development, internal communications, and on the job performance support.

Job Summary

In this role, you will be focused on driving the strategy for the L&D workstream on major business initiatives. As a Strategist you'll be responsible for providing insight and recommendations on what training is needed, what methods and mediums are used, what communications and change management is needed and if any additional resources are needed for a given project. You'll collaborate with teams across CS in order to plan, design and implement your strategy successfully and on time. This role will test your organization, communication and time management skills on a daily basis.

What you'll do:

Own L&D workstreams to include:

  • Creating comprehensive L&D strategies for major business initiatives
  • Collaborating with teams to ensure projects stay on track and will be effective. Teams including WFM, PMs, Analytics, Content, Design, Direct CS and any other departments relevant to a given project
  • Designing engaging and impactful training programs
  • Facilitating training sessions
  • Upskilling L&D Specialists as needed for facilitation support
  • Gathering and analyzing feedback and data in order to quickly iterate content as needed
  • Create process to streamline core work and share best practices
  • HLUs
  • Run team meetings
  • Mentor and coach L&D Specialists
  • Represent Lead as needed in meetings


You have:

  • Minimum of 2 years of professional Learning & Development experience
  • Portfolio that shows work that made it through completion, including success and failures
  • Experience speaking to goals, objectives and outcomes of work
  • You may be a good fit if are skilled at:
  • Planning You are able to handle your own scoping and set proper expectations with your cross-functional team
  • Collaborating You are able to work with your cross-functional team to determine goals and success of individual projects
  • Communicating You can effectively communicate and present your work to your teams, partners and peers.
  • Influencing You can manage and deliver succinct and exec level summaries and messaging to various levels of leadership orally and in written form.
  • Supporting You keep the team inspired with new tools and trends and proactively surface new ways for us to streamline our design process
  • Mentoring You can provide guidance, coaching, insight and development opportunities for the growth and development of your mentees.
  • Implementing You always produce quality deliverables with little guidance from others or defined frameworks; establish processes and best practices are adopted by your teams.

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. Block 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.

More Information on Square
Square operates in the Fintech industry. The company is located in San Francisco, CA, Atlanta, GA, St. Louis, MO, Salt Lake City, UT, New York, NY, Denver, CO and Seattle, WA. Square was founded in 2009. It has 6769 total employees. It offers perks and benefits such as Flexible Spending Account (FSA), Disability Insurance, Dental Benefits, Vision Benefits, Health Insurance Benefits and Life Insurance. To see all 598 open jobs at Square, click here.
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