Director of Sales, Canada

Heidi AI Care Partner

Heidi is the AI Care Partner built for clinicians. We started with documentation because that's where the invisible tax is heaviest — the 60 minutes after clinic, the screen between clinician and patient, the notes that follow you home. Today, the platform spans Scribe, Evidence and Comms: a connected system that absorbs administrative load across the full clinical day so clinicians can focus on what they trained to do.

About one in three people at Heidi is a clinician. That shapes how we build, how we write and how we sell. We speak from inside the clinic, not from outside looking in. If that sounds like the kind of company you want to represent, read on.

The Role

Canada is one of our most important markets right now. The healthcare system is genuinely struggling: clinician burnout, growing access gaps, documentation piling up. This is the moment Heidi was built for. You'll run a team of 8–12 Account Executives and Sales Associates spread across the country. The job is the full picture: pipeline, deals, team development, forecasting. Day-to-day you'll work closely with our Directors of Marketing and Government Affairs for Canada, and with Customer Success, to make sure what clinicians are promised is actually what they get. This role reports directly to the General Manager, Canada.

What You'll Do

• Manage and develop a team of 8–12 AEs and Sales Associates across Canada, clear on expectations, consistent in your 1:1s, and serious about building a team people actually want to stay on
• Own the Canadian sales number: forecast accurately, identify risks early and close the gap when it matters
• Build and execute a national go-to-market strategy that actually fits Canada, accounting for provincial funding quirks, regional variation, and procurement timelines that don't move on anyone's preferred schedule
• Partner with Marketing to align on pipeline targets, campaigns and messaging that land with Canadian clinicians and health system buyers
• Work with Government Affairs on provincial digital health initiatives, public tenders and health authority relationships. There's real opportunity here if you know how to navigate it
• Collaborate with Customer Success to ensure smooth handoffs, healthy retention and expansion within existing accounts
• Own the sales playbook for Canada: how we qualify, how we stage deals, how we price, how we handle the objections that come up again and again in this market
• Sit at the leadership table alongside the General Manager, Canada. This is a seat with real input into market strategy, not just a reporting line
• Spend real time building relationships with enterprise and health system buyers across provinces, the kind of relationships that take more than a few calls to develop

What We're Looking For

• A track record in sales leadership. You've run quota-carrying teams, had to develop people who weren't quite there yet, and hit numbers that didn't happen by accident
• Genuine knowledge of the Canadian healthcare landscape. You've sold into health systems, provincial bodies or clinical practices and you know how purchasing decisions actually happen, not just in theory
• Background in health tech, digital health or complex SaaS. You're used to long cycles, multiple stakeholders pulling in different directions and procurement processes that will test anyone's patience
• A collaborative streak. Marketing, CS and Government Affairs need a real partner in sales, not someone who treats them as support functions. The best outcomes here come from working together
• Directness, with your team, across the org and upward. Problems that get flagged early are problems that get fixed. We don't want to find out about issues at the end of a quarter
• Comfort with ambiguity. Heidi is moving fast and some of the structure you'd expect in a larger org simply isn't there yet. Parts of the playbook exist; you'll build the rest
• Bilingual (English/French) is a strong asset, particularly given our growth in Quebec

What Success Looks Like

In your first 90 days, you should know your team well enough to say where the gaps are, have a real handle on the pipeline, and have a point of view on where the biggest Canadian market opportunities are going to come from.

At six months, the team has a consistent way of working, the cross-functional relationships are genuinely functional and you're hitting your targets without anyone having to chase you on forecasting.

At year one, you've built something the team is proud of, we've meaningfully grown our presence with major health systems and clinics across the country, and you're already thinking about what doubling the team looks like.

Why Heidi

• The product resonates with clinicians in a way that most health tech doesn't. That makes a real difference in how sales conversations go
• You're not walking into a fully defined role. There's real scope to shape how the Canadian function works: the team, the approach, the relationships
• The General Manager and cross-functional leads here take sales seriously. You won't be fighting for resources or credibility
• Competitive base, performance incentive and equity. We'll share the specifics as we get to know you
• Fully remote across Canada. We measure output, not hours logged or office attendance