Enterprise Account Executive

Description:

Dialogue, Canada’s leading virtual care provider, is seeking a driven and experienced Enterprise Account Executive – Eastern to join their high-performance sales team in Montreal, QC. This full-time role is focused on building strategic partnerships with enterprise clients (2,000+ employees) across Eastern Canada, helping to shape the future of virtual healthcare delivery in the region.

Reporting to the Director of Enterprise Accounts, you’ll serve as a trusted advisor and champion of Dialogue’s Integrated Health Platform®, which offers a full suite of health and wellness solutions including primary care, mental health, iCBT, EAP, and wellness programs. You’ll be instrumental in connecting Canada’s most prominent employers with innovative solutions that drive employee well-being, satisfaction, and retention.

Key Responsibilities:

• Own the complete enterprise sales cycle, from lead generation through to contract closure, targeting major employers across Eastern Canada.

• Build and manage a high-value pipeline by leveraging inbound leads, strategic partnerships, and proactive outreach strategies.

• Deliver tailored, high-impact presentations and product demos to C-suite and executive-level decision-makers, both virtually and in person.

• Collaborate across departments—Sales, Marketing, Business Development, Customer Success, Medical Ops, Finance, HR, and Legal—to ensure alignment and deal progression.

• Maintain pipeline hygiene and accurate forecasting through Salesforce CRM and structured sales methodologies.

• Partner with the Marketing team to co-create targeted campaigns, thought leadership content, and events that generate enterprise demand.

Ideal Candidate Profile:

• 8+ years of B2B enterprise sales experience, preferably with a background in strategic, complex solution selling.

• Exceptional storytelling, communication, and consultative sales capabilities.

• Demonstrated success in executive stakeholder engagement and long-cycle sales.

• Deep passion for improving access to healthcare and wellness for Canadians.

• Professional presence, integrity, and client-first mentality.

• Bilingual in English and French (essential to serve clients across Canada).

• Strong familiarity with Salesforce and sales enablement tools.

Bonus Qualifications:

• Experience in the healthcare, employee benefits, or insurance sectors.

• History of selling to HR, Finance, or Operations leaders in large organizations.

What Dialogue Offers:

Dialogue fosters a culture of excellence, impact, and community while providing industry-leading benefits, including:

• Access to Dialogue’s virtual care and mental health platform for you and your family.

• Fully funded health, dental, and wellness benefits including fitness reimbursements.

• Generous vacation and leave policies: 4 weeks vacation, 9 wellness days, and 1 volunteer day per year.

• Flexible hybrid work setup (3 days/week in-office in Montreal or Toronto).

• Work abroad flexibility up to 4 weeks/year.

• Competitive incentive plans, referral bonuses, and RRSP matching.

• Continuous learning with Coursera, mentorship programs, and training budgets.

• Parental leave top-up (optional).

About Dialogue:

Dialogue is Canada’s #1 virtual healthcare provider. Through its Integrated Health Platform®, Dialogue delivers a holistic suite of services that improve physical and mental well-being for millions of Canadians. The company is on a mission to transform health and well-being by bringing together great people who are driven by impact, growth, excellence, and community.

With a strong commitment to diversity and inclusion, Dialogue provides a welcoming space for all team members and applicants.