Dialogue is looking for a Toronto-based Account Executive (AE) to join our team! We understand there are a lot of different account executive positions to consider, but this role offers a unique opportunity to be a key contributor as we protect our position as the market leader, in the fast-maturing virtual healthcare space. If you're not familiar with virtual healthcare, the industry has evolved from being seen as nice-to-have in the eyes of leading employers to now aligning with key priorities, becoming the most essential benefit Canadian companies are investing in. The great news is that while adoption is high with top employers, only ~10% of Canadian businesses currently offer this service today. As this disruptive offering approaches a tipping point, where employees expect virtual healthcare to be apart of their benefits package, a massive opportunity awaits… 

We are looking for someone to join our Toronto office to work with accounts headquartered in the GTA, which means you’ll be selling Dialogue to some of the best brands in Canada. 


In this role, you will:

  • Manage the end-to-end sales process. This includes, but is not limited to identifying, qualifying, capturing, and closing complex sales within companies that have less than 1000 employees;
  • Collaborate with Sales, Business Development, Marketing and Customer Success to create content and material for sales engagements
  • Follow a defined sales process and record all activities in our CRM;
  • Work closely with the Sales Development Representatives (SDRs) to optimize addressable market coverage and generate pipeline/revenue opportunities; 
  • Leverage Marketing and Business Development leads, with Partnerships and direct AE prospecting to source sales engagements.
  • Feel right at home presenting Dialogue to executives of prospective customers, both virtually and in-person.

What we’re looking for:

    • Passionate professionalism: remember, you’re selling to some of the best brands in Canada in a highly competitive space. Your presence, passion, and professionalism represent key differentiators. 
    • A mission-oriented mindset: we are selling a service that removes barriers to accessing quality physical and mental healthcare, and positively impacts the health, wellness, and well-being of hundreds of thousands of Canadians. If you got excited at the prospect of being a driving force in turning the aforementioned hundreds of thousands into millions of Canadians, you’re in the right place. Want to read why our VP Sales, Zack Brown, joined Dialogue? Check it out here.
    • Experience with strategic selling in a complex environment: Minimum 5 years of enterprise selling experience, involving relationship management, sales acumen and rigor. Evangelical selling experience, requiring excellent communication and storytelling are also critical skills to achieving success in the unique virtual healthcare space.


  • It’s even better if you also have: 
    • Experience selling to HR, Operations and/or Finance;
    • Experience within the insurance industry;
    • Experience using Salesforce.


What we can offer you:

  • The opportunity to have an impact in an early-stage, well-funded company that is doubling in size annually;
  • Being part of a of hard-working team, ambitious and caring individuals who will help you learn and grow professionally;
  • A competitive salary, stock options and a generous time-off policy;
  • Top tier benefits plan including unlimited access to Dialogue for you and your family, a comprehensive parental leave program, wellness membership reimbursement and much more.

Apply for this Job

* Required