Enterprise Account Executive - Eastern

Your role as Enterprise Account Executive – Eastern

Reporting to the Director, Enterprise Accounts, your mission will be to engage with enterprise-level organizations (2,000+ employees) across Eastern Canada. You will focus on building strategic relationships with some of the country’s most prominent employers, championing our virtual healthcare solutions to positively impact the lives of Canadians.

We’re looking for a high-performing, purpose-driven sales professional who thrives in a dynamic environment and is excited by the opportunity to sell meaningful solutions in the health and wellness space.

What you’ll be doing: 

• Own the end-to-end sales cycle: From prospecting and qualification to solution development and closing, targeting companies with 2,000+ employees across Eastern Canada
• Build and manage a pipeline of high-value opportunities by leveraging inbound leads, partnerships, and proactive outreach
• Present with impact: Confidently deliver tailored pitches and demos to executive-level stakeholders (virtually and in-person), positioning Dialogue as a strategic healthcare partner
• Collaborate cross-functionally with teams across Sales, Business Development, Marketing, Customer Success, Medical Operations, Finance, HR, and Legal to ensure alignment and deal velocity
• Document activity in CRM (Salesforce) and follow a structured sales methodology to maintain pipeline hygiene, forecast accurately, and share insights across the team
• Partner with Marketing to co-develop content and campaigns to support enterprise growth

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

• A mission-driven mindset: You’re passionate about improving access to quality physical and mental healthcare for Canadians
• 8+ years of enterprise B2B sales experience, ideally with a focus on complex, strategic solution-selling and executive stakeholder management
• Exceptional communication and storytelling abilities, with a knack for translating complex ideas into clear, compelling messages
  A consultative approach: You lead with curiosity and insight, understanding business needs before presenting solutions
• High professionalism and executive presence: You represent Dialogue with passion and integrity, always putting the client experience first

Bonus points if you have:

• Experience in the healthcare, benefits, or insurance industry
• Experience selling to HR, Operations, and/or Finance leaders

Familiarity with Salesforce and other sales enablement tools

Please note that as we serve customers across Canada, bilingualism is essential for this position. You will be required to communicate in French and English.

• Access to the Dialogue app and virtual mental health support for you and your family
• Fully funded insurance, 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
• Optional parental leave top-up

About Dialogue

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:

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 [email protected].