Director of Sales, Canada

Head of Sales, Canada

Heidi is the AI Care Partner built for clinicians, designed to alleviate the administrative burden of documentation and allow healthcare professionals to focus on patient care. Our platform spans Scribe, Evidence, and Comms, offering a connected system to absorb administrative load. With a significant portion of our team being clinicians, we build and operate with deep empathy for the healthcare ecosystem.

Canada represents a crucial market for Heidi. The healthcare system faces significant challenges, including clinician burnout and growing access gaps, making Heidi's solutions more critical than ever. As the Head of Sales for Canada, you will lead a team of 8-12 Account Executives and Sales Associates, driving the full sales cycle from pipeline management to deal closure and team development. This role requires a strategic thinker with a deep understanding of the Canadian healthcare landscape and a proven ability to execute a national go-to-market strategy.

What You’ll Do:

• Manage and develop a team of 8-12 Account Executives and Sales Associates across Canada, fostering a high-performance and supportive team environment.
• Own the Canadian sales number, including accurate forecasting, risk identification, and proactive gap closure.
• Develop and execute a national go-to-market strategy tailored to the Canadian market, considering provincial nuances and procurement timelines.
• Partner with Marketing to align on pipeline targets, campaigns, and messaging for Canadian clinicians and health system buyers.
• Collaborate with Government Affairs on provincial digital health initiatives, public tenders, and health authority relationships.
• Work with Customer Success to ensure seamless handoffs, healthy retention, and expansion within existing accounts.
• Own and refine the sales playbook for Canada, including qualification, deal staging, pricing, and objection handling.
• Actively participate in leadership discussions, providing significant input into market strategy.
• Build and nurture relationships with enterprise and health system buyers across provinces.

What We’re Looking For:

• Proven track record in sales leadership, managing quota-carrying teams and achieving sales targets.
• Genuine knowledge of the Canadian healthcare landscape, with experience selling into health systems, provincial bodies, or clinical practices.
• Background in health tech, digital health, or complex SaaS environments, understanding long sales cycles and multi-stakeholder environments.
• A collaborative approach, working effectively with Marketing, Customer Success, and Government Affairs.
• Direct and transparent communication style, flagging issues early.
• Comfort with ambiguity and a proactive approach to building structure in a fast-paced environment.
• Bilingual (English/French) is a strong asset, particularly for Quebec market engagement.

What Success Looks Like:

• First 90 Days: Deep understanding of the team, a clear view of the pipeline, and identification of major Canadian market opportunities.
• Six Months: Consistent team working methods, functional cross-functional relationships, and target achievement without forecasting issues.
• One Year: A proud team, significant growth in major health systems and clinics across Canada, and strategic planning for team expansion.

Why Heidi:

• Impactful Product: Our product resonates deeply with clinicians, simplifying conversations and driving adoption.
• Shaping the Function: Significant scope to define and build the Canadian sales function, team, and approach.
• Leadership Support: Sales is taken seriously, with ample resources and credibility.
• Compensation: Competitive base salary, performance incentive, and equity.
• Flexibility: Fully remote across Canada, focusing on output and results.