Enterprise Account Executive, West

Dialogue is the #1 virtual care provider in Canada. By developing our Integrated Health Platform🅫, we provide exceptional online health and wellness programs (primary care, mental health, iCBT, EAP, and wellness) to organizations that want to improve the wellness of their employees and families.

When it comes to our work, we set the bar high. Together, we’re transforming health and helping millions improve their well‑being. We’re firm believers that great people don’t settle on:

• Impact
• Community
• Growth

Feel like you can make a difference? Good news, we saved you a seat!

Come as you are. As a proud equal‑opportunity employer, Dialogue is dedicated to creating a diverse and inclusive workplace for everyone. Qualified applicants will be considered regardless of citizenship, ethnicity, race, colour, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status. Applicants who require specialized accommodation are encouraged to contact accessibility@dialogue.co.

Your role as Enterprise Account Executive, West

The mission of the Regional Account Executive will be to create a go to market strategy for all of Alberta to build the Dialogue brand and to grow the Dialogue business. This will include Enterprise accounts however full market coverage is key to the success of this role. We’re looking for someone who is motivated by this enormous opportunity to have a positive impact on the health of Canadians.

What you’ll be doing:

• Manage the full sales cycle, from prospecting and qualification to closing complex deals, primarily with companies of 2,000+ employees
• Collaborate cross‑functionally with Sales, Business Development, Marketing, and Customer Success to develop compelling content and materials for sales engagements
• Follow a structured sales process and maintain accurate records in our CRM, ensuring seamless collaboration across teams including Go‑to‑Market, Medical Operations, HR, Finance, and Legal
• Leverage multiple channels —including Marketing and Business Development leads, strategic partnerships, and direct outreach—to drive new business opportunities
• Build and maintain strong relationships with key brokers and advisors, both locally and nationally
• Confidently present Dialogue’s value proposition to executive‑level stakeholders through virtual meetings and in‑person presentations

We'd love to hear from you if you have:

• Passionate professionalism – You’re not just selling a product; you’re representing health and care to some of Canada’s top brands in a fast‑paced, dynamic space. Your energy, credibility, and presence are key differentiators
• A mission‑driven mindset – You believe in making healthcare more accessible. Our services break down barriers to quality physical and mental healthcare and positively impact the lives of millions of Canadians
• Proven experience in strategic, complex sales – You bring 5+ years of experience selling to enterprise accounts, with a focus on building relationships, demonstrating strong sales acumen, and operating with discipline and structure
• An evangelical sales approach – You thrive in a consultative sales environment, combining excellent storytelling and communication skills with a deep understanding of the unique dynamics of the virtual healthcare space

It’s even better if you also have:

• Experience in the health and benefits or insurance industry, with a solid understanding of the ecosystem and client needs
• A track record of selling to HR, Operations, and/or Finance leaders, with the ability to tailor messaging to each stakeholder group
• Experience selling into the public sector and/or financial services industry, navigating their unique procurement processes and compliance requirements
• Familiarity with Salesforce or similar CRM platforms, with a disciplined approach to pipeline management and sales reporting

At Dialogue, your well‑being is our priority

Taking care of others also means taking care of our team! Depending on your role and employment status, you could have access to the following benefits:

• Access to the Dialogue app and virtual mental health support for you and your family
• Fully funded insurance, a health spending account, dental coverage, and fitness reimbursement
• 4 weeks vacation, 9 wellness days, and 1 volunteer day
• Hybrid work: 3 days/week in our Montreal or Toronto offices, excluding remote roles
• Work abroad up to 4 weeks/year
• Incentive plans, referral bonuses & RRSP matching
• Learning via Coursera, external training budget & mentorship