Go-To-Market Strategy Project Manager, Sales Strategy

  • Chicago, IL
  • Employees can work remotely
  • Full-time
  • Alternate Location: Toronto, Canada

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 is looking for a data-driven person with experience launching and scaling Sales teams in new markets to join our Sales Go-to-Market (GTM) Strategy team. Square's Sales team are master storytellers that promote revenue growth for Square by understanding our sellers' needs and onboarding them onto our outstanding ecosystem to grow their businesses. Sales GTM Strategy determines how we go to market and looks for growth levers for our business.

You will build the strategy for Sales teams in new markets and work with other teams to set new Sales teams up for success by defining new lead sources, conducting analysis on our customer profile, and building tracking and reporting on important metrics. You will also help identify opportunities for growth with product teams and develop an optimized team structure. You are comfortable with experimentation to ensure the team is iterating and achieving our goals. You will be in a role that is a hybrid of traditional jobs in analytics, strategy and planning, project management, and financial analysis. You will be an individual contributor initially, but people management opportunities will be available for high-performing candidates in the future. You will report to the Sales GTM Strategy lead and partner with senior sales leadership and other teams to identify opportunities and promote growth.

You will also: 

  • Develop a strategy for launching and scaling Sales teams in new markets
  • Analyze data and find insights to guide strategic decisions and enhance Sales' ability to go-to-market, such as new market launches, customer segmentation definition, and lead generation programs
  • Independently identify growth opportunities, lead discussions to advocate for resourcing the project, lead the project, and implement tracking infrastructure and visualization to report on results
  • Manage relationships with Partnerships, Product, Marketing, Finance, Data Science, and more to promote Sales growth and profitability
  • Direct data analysts to create reporting and sources of truth


You Have:

  • 5+ years of strong analytical and problem-solving experience (top-tier management consulting, corporate strategy, sales/business operations, GTM strategy, or similar)
  • Experience launching GTM teams (Sales preferred) or products in new markets
  • Experience working with and motivating teams in a growing environment
  • You have excellent written and verbal communication skills, proven ability to communicate and manage relationships with senior executives, and can work effectively with all levels
  • You are an entrepreneurial, strategic thinker and are excited to dive into tough problems and build new processes / deliverables from scratch; you develop frameworks to support strategic decisions and are accomplished at detailed execution
  • Highly quantitative with demonstrated ability conducting complex data analysis to build actionable insights through a combination of SQL (strong proficiency preferred), Excel/Google Sheets (can perform complex functions), and Looker (or similar data visualization tool)

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

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.

Privacy Policy