Director of Sales, Canada

Heidi•Toronto, ON

1d•Remote

About The Position

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.

Requirements

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

Nice To Haves

Bilingual (English/French) is a strong asset, particularly given our growth in Quebec

Responsibilities

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