Who you are

• 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
• A mission-driven mindset: You’re passionate about improving access to quality physical and mental healthcare for Canadians
• 3+ 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
• 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

What the job involves

• Reporting to the Director, Enterprise Accounts, your mission will be to engage with enterprise-level organizations (2,000+ employees) across Central 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
• Own the end-to-end sales cycle: From prospecting and qualification to solution development and closing, targeting companies with 2,000+ employees across Central 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

Benefits

• Unlimited Dialogue access for you and your immediate family
• Flexible working hours to improve work-life balance
• Gym membership reimbursement
• Top-tier benefits (or health) plan for you and your family
• Delicious, healthy snacks and refreshments delivered to the office every week
• A beautiful new office in Old Montreal, and another conveniently located at Queen and John St. in Toronto
• A competitive salary and stock options in the company
• Paid time off to volunteer and give back to the community
• The opportunity to learn and grow professionally