Account Executive, Canada

  • Toronto, Canada
  • Full-time

Company Description

We believe the economy is better when everyone has access. When everyone has room to grow. No one should be left out because the cost is too great or the technology too complex. We started with a little white credit card reader but haven’t stopped there. We’re empowering the independent electrician to send invoices, setting up the favorite food truck with a delivery option, helping the ice cream shop pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re here to help sellers of all sizes start, run, and grow their business—and helping them grow their business is good business for everyone.

Job Description

Our Sales organization is looking for a skilled sales professional with experience  selling to senior executives 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 commerce channels and capabilities. 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:

  • Consistent overachievement of quota in current and previous roles

  • 4+ years of experience in sales, business development or a similar quota carrying client-facing role

  • Previous experience in outbound sales and prospecting in Canada

  • A BA/BS degree

  • Excellent written and verbal communication skills 

  • Shown ability to multi-task and run multiple projects while paying strict attention to detail

  • An assertive, resilient and persuasive personality

  • An analytical, structured thought process with the ability to assess business opportunities and read prospective buyers

  • The ability to garner support from internal experts and external partners to position Square against competition

  • Genuine curiosity about people and business, and possess the innate ability to inspire passion in others

  • Coachability, interest in implementing feedback, and dedication to the consistent improvement of your craft

  • The ability to adapt to new situations quickly and think on your feet

  • Hustle and determination

  • Ability to close sales

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.