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Account Executive - SMB (Toronto)

  • Thread starter Thread starter Contra
  • Start date Start date


Who We Are And What We Do:

Contra is revolutionizing the world of work. Contra provides companies with an industry-leading, all-in-one platform to manage and scale their flexible workforce. In a world where work is becoming more flexible and project based, Contra is leading the way in making the world’s platform for project based and flexible work. Our platform offers all the necessary tools for hiring, onboarding, managing, and paying flexible talent. Contra has raised over $44M from top VC’s including NEA, Unusual Ventures and Cowboy Ventures.

Why Join Contra's Journey?

Contra isn’t just another HR tool. Contra is building a new type of platform for the future of work. As both people and companies look to adopt more flexible working styles and talent strategies, we are leading the way, with a network of over 500k freelancers and 15k clients who depend on Contra to work together and collaborate, 100% commission free.

About You:

You are a hungry, energetic and Account Executive professional skilled in engaging with various organizational levels, including C-level executives.

You have a deep understanding of the buyer's journey, and you excel in complex sales environments.

You can confidently identify client needs and demonstrate how Contra's platform is and can become an integral part of a companies talent strategy.


  • Manage a targeted account list, developing strategies to win business with SMB targets, focusing on early to growth stage technology companies and medium sized creative agencies.
  • Meet or exceed sales targets on a monthly, quarterly, and yearly basis.
  • Develop a robust sales pipeline through personal outreach, team collaboration, and management of outbound prospects.
  • Navigate through organizations to map stakeholders, build champions, and close deals with decision-makers.
  • Maintain up-to-date records in Hubspot with customer information, forecasts, and pipeline data.


  • 3+ years of sales experience in either SMB, Mid Market and Growth Stage Technology segment.
  • Proven track record in developing new business and adding net new logos.
  • Ability to build relationships with senior executives in mid-sized companies.
  • A hunter mentality, coupled with a strong sales acumen and eagerness to learn.
  • Passion for working in a fast-paced startup environment.
  • Ideally located in Toronto, Canada

Total Comp:

Contra offers competitive pay, scalable benefits, and perks.

  • Uncapped commission structure. Top performers have the ability to earn over $100k. Base depends on the interview process and typically we share this in interview 1 or 2
  • 100% health coverage + 99% dental coverage for US full-time employees, and health reimbursements for Canadian employees and international contractors


  • $4,000 laptop reimbursement upon starting
  • Opportunities for stock grants
  • Flexibility in work location - Contra is fully remote, with hubs in SF + NY + Toronto.

Interview Process

  • Intro Call with the Recruiting Team
  • Interview #1 with Head of Operations
  • Interview #2 Role Playing
  • Interview with CEO & Co-Founder

Contra is an equal opportunity employer, committed to diversity and inclusion. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Note: Contra communicates with applicants through @contra.com domains only. We never ask for money from potential employees. For the latest job postings, visit Contra Careers.

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