Content Specialist Lead

  • San Francisco, CA
  • Employees can work remotely
  • Full-time

Company Description

Square builds common business tools in unconventional ways so more people can start, run, and grow their businesses. When Square started, it was difficult and expensive (or just plain impossible) for some businesses to take credit cards. Square made credit card payments possible for all by turning a mobile phone into a credit card reader. Since then Square has been building an entire business toolkit of both hardware and software products including Square Capital, Square Terminal, Square Payroll, and more. We’re working to find new and better ways to help businesses succeed on their own terms—and we’re looking for people like you to help shape tomorrow at Square.

Job Description

Square’s Customer Education Team is looking for a lead to increase Seller self-service adoption, improve Square's pre-contact experience, and champion launch workflows. Square’s Content Specialists equip Sellers with technical product resources and foundational business knowledge, empowering them to independently navigate how to start, run, and grow the business of their dreams. You will manage the performance of a growing team of US Content Specialists, who work with a wide variety of internal teams to develop the content strategy and launch customer resources to improve the Seller support experience for products and services at Square. Our content launches range from small feature updates to large product launches, spanning Hardware to POS to Partnerships to SaaS. On top of building a high performing team, the Content Specialist Lead will drive team results through active analysis of support resource performance, and partner with several cross-functional partners across CS, Onboarding, Marketing, Product, Localization, Compliance, Legal and Communications. 

The Content Specialist Lead will direct the strategy of the US Content Specialist team, identify new ways to educate Square Sellers, measure impacts and bring visibility to the Content Specialist projects, needs, and success. Effective team leadership, cross-team coordination, project management, and an ability to influence key stakeholders are essential.

You will:

  • Manage and measure a growing team of Content Specialists, ensuring content is published within team SLAs. 

  • Lead and participate in launch planning meetings. Provide guidance on delegation of tasks and team support strategy. 

  • Set clear expectations and drive improvements to the product launch process; hold Product Teams accountable to communicating and collaborating on resources well in advance of a launch.

  • Work with the CS analyst and engineers to identify self-service support successes as well as areas of opportunity for the Seller support experience. 

  • Surface trends in the Seller self-service and direct support experience to help inform key changes, improvements, and resources available to drive team and organization wide KPIs (Value Generation, Self-service adoption, Availability, Messaging, Customer Experience).

  • Define the Content Specialist Team strategy and vision, constantly seeking program/workflow improvement.

  • Build staffing strategy to ensure adequate coverage for all products and customer segmentation.

  • Maintain in-depth knowledge of Content Specialist workflows, dependencies, limitations, timelines, cross-functional partners, and project proposal requirements.


  • University degree and 3+ years relevant experience successfully managing technical, customer-facing teams with metrics to prove it or 2+ years of technical/product writing experience with examples of launching large projects, measurable results, and improvements to content launch workflows.  

  • Experience influencing critical decisions within cross-functional organizations without direct authority.

  • Strong command skill, decision quality, and ability to confront team and/or cross-functional partners to hold them accountable to documented expectations.

  • Ability to be creative, strategic, analytical, and think outside the box to solve problems.

  • Strong project management and time management skills.

  • Interpersonal skills with a keen ability to explain complex concepts across the organization and to large audiences.

  • Thrives in a fast-paced environment with competing priorities.

  • Strong drive for results, proven ability to develop direct reports and others.

Additional Information

At Square, we value diversity and always treat all employees and job applicants based on merit, qualifications, competence, and talent. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We will consider for employment qualified applicants with criminal histories in a manner consistent with the requirements of 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.


At Square, 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

Square, Inc. (NYSE: SQ) builds tools to empower businesses and individuals to participate in the economy. Sellers use Square to reach buyers online and in person, manage their business, and access financing. Individuals use Cash App to spend, send, store, and invest money. And TIDAL is a global music and entertainment platform that expands Square's purpose of economic empowerment to artists. Square, Inc. has offices in the United States, Canada, Japan, Australia, Ireland, Spain, Norway, and the UK.

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