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Groupdesk is bringing modern software development to the travel industry.

About Groupdesk

As travel industry and software experts, we created the first ERP and online retail solution designed specifically to face the challenges of group travel. We are a growing team of developers and operators who are passionate about travel.

Our product currently manages bookings for thousands of travelers and processes hundreds of thousands of financial transactions each year.

Available Positions

Don’t see a position but think you can make a difference? Contact us.

Head of Sales

Who we are
Groupdesk is creating a future where sustainable growth is achievable for all travel operators across the globe by providing a global SAAS platform where all travel operators can book customers faster with higher yields and manage their business efficiently, from anywhere. Today, our market represents a $157bn opportunity and we believe ultimately that we can help steward the next generation of travel businesses to more profitability, flexibility and great customer experiences. We are looking to add a Head of Sales to our team to help us continue to scale!

Role description:

Groupdesk is looking to add a Head of Sales to our team. As part of our senior leadership, you will have a unique opportunity to not only shape our sales function and help scale it out, you will also have a voice in key business decisions that affect our entire operation.

You will:

  • Prospect – in our experience, this includes attending trade shows, cold calling (yes with a phone), cold emailing and doing lots and lots of demos with interested leads.
  • Manage your own sales pipeline with high velocity and detailed notes
  • Provide regular updates to colleagues and the Co-Founders
  • Help identify new verticals where we can win and develop a go to market strategy for launch
  • Help shepherd clients through our Pre-Sales process in partnership with our Head of Implementation
  • Develop forecasting and sales performance metrics
  • Take personal accountability for revenue targets – while our Co-Founders both sell, the sales goals are your primary responsibility

You should:

  • Be great under pressure. Pressure looks like aggressive sales targets, travelling an average of 1x/month and needing to be flexible in making client calls outside of typical work hours. We sell into many time zones today and try to be as accommodating as possible to close the sale.
  • Have experience in selling complex solutions to a market in transition (can be software, hardware, widgets etc – tell us your story!)
  • Be very comfortable with working remote 
  • Enjoy working collaboratively with other teams
  • Experience in selling in a SaaS environment
  • domain experience, primarily in Airlines or Hotels 
  • Have a history of exceeding personal sales goals 
  • Be energetic, positive, and solution focused – we are a start up – we do not have it all figured out and want your help in doing so
  • Be cool under pressure 
  • Be entrepreneurial – we need someone in this role who sees opportunity and takes it without waiting to be asked or given permission

Our Values:

  • We are passionate for travel and travel technology 
  • We love to win and thrive in a fast-paced environment
  • We love to play as a team and we know we need to make each other better 
  • We believe in getting stuff done with a customer-first attitude
  • We believe in being honest with each other, learning quickly to move faster and elevate our whole team


  • Remote friendly work environment. Many of our team are located across Canada and even our Toronto based team are spread out over 3 hours and often work from home to better balance family and personal commitments. No sitting on the train for 3 hours just to get into work everyday. 
  • You can be based in Canada, US, EU or UK. We typically sell into EST and CST time zones and if you are located elsewhere, you should expect to align your workday with those at least 3 days a week. 
  • We have an office in Toronto and it is close to Queen & Spadina.
  • We offer Ritual lunch credits bi weekly 
  • Annual in person retreat – we bring together our teams once a year offsite to re-align on goals, bond and get to know one another outside of our code 🙂


The salary range for this role is between $70,000 CAD – $90,000 CAD with generous commission based on sales paid quarterly after client close as well as equity. Salary range is dependent on experience, equity and commission structure to be decided and agreed upon by the successful candidate and our team. 

Please send your resume to our Co-Founder and CEO, Janice Sousa at

Apply Now

How to Apply

Contact us at or use the form below to reach out. Please include your resume and location.