Account Executive, Canada

  • Toronto, Canada
  • 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

Our Sales organization is looking for an Account Executive to help grow our footprint into strategic accounts. You have a passion for problem solving and finding opportunities for Square to help companies improve and expand their business. You are a relationship builder, great listener, collaborative partner, dynamic project manager, proactive problem solver and strategic thinker. Your entrepreneurial spirit and passion for problem solving will help in identifying ideal merchants that can grow with Square’s platform. You’re a quick learner, and you have a proven track record of negotiating and closing complex deals.

The successful candidate will have experience driving cross-functional internal teams, be comfortable dealing with uncertainty in a fast-paced environment, and be able to put structure to nebulous problems. Your are highly entrepreneurial and have the ability to thrive under minimal guidance.  We are looking for an individual that has a breadth of functional experience in sales, business development, partnership building, and the ability to articulate complex systems to executives. 

You will:

  • Lead the charge introducing Square to merchants in all verticals: retail, food and beverage, professional services, etc

  • Own the sales cycle from prospect to close and partner with internal teams to ensure successful on-boarding

  • Consistently achieve and exceed quarterly goals 

  • Act as an innovative, trusted advisor for both clients and internal partners

  • Collaborate with Payments, Product, and Marketing teams to channel the customer voice internally, impact product roadmaps, and ensure our solutions meet the needs of the market 

  • Leverage your prior sales experience to inform a creative go to market strategy

  • Thrive in operating in a dynamic and rapidly changing environment that is prone to change

  • Be aware of the unique opportunity you have to make a difference in the lives of the people you engage with


You have:

  • A BA/BS degree or relevant experience 

  • 2+ years in a prospecting sales role required

  • Consistent success against quota

  • Experience selling a complex ecosystem of products

  • Hunting and cold outreach experience

  • Excellent written and verbal communication skills

  • Collaborative and team player mentality

  • Salesforce CRM experience a plus

  • The ability to drive deals independently in a fast-paced, dynamic environment

Additional Information

At Square, our purpose is to empower – within and outside of our walls. In order to build the best tools for the businesses and customers we support all over the world, we have to start at home with a workforce as diverse and empowered as our sellers. To this end, we take great care to evaluate all employees and job applicants equally, based on merit, competence, and qualifications. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We encourage candidates from all backgrounds to apply. 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.