Head of Revenue ( Founding ) (Toronto)

About Stem Health

Stem Health is reimagining the primary care experience for individuals who want a more thoughtful relationship with their health. Physician‑led and membership‑based, we combine medical excellence with the warmth of hospitality anchored in a beautifully designed flagship clinic at First Canadian Place, opening September 2026. Our care model is relationship‑based, data‑informed, and built on time, trust, and exceptional service.

The Mandate

Stem Health generates revenue across two distinct motions: B2B executive health programs sold to employers and delivered through advisors and benefits intermediaries, and a direct‑to‑consumer private membership. Both are active from day one. As our founding Head of Revenue, you own both and you own them by selling, not by directing from the deck. This is not a seat for someone who last sold three years ago. It is for a closer who still loves the craft, who has built revenue engines from scratch before, and who understands that the most important thing a founding commercial leader can do is personally close the first cohorts, learn what reliably converts, and harden that into a documented, repeatable system. The seat scales to full revenue leadership multi‑site, broader team, CRO scope as the motion is proven.

What You Will Own

• Establish the revenue motion the architect
  • Define how Stem Health generates revenue. Own pricing, packaging, and the commercial offer for both motions: the B2B executive health programme and the D2C membership along with the ideal‑customer profile and qualification criteria behind each.
  • Write the playbook. Convert what actually closes into a documented, repeatable motion per channel: stage definitions, objection handling, sales collateral, and the cadence each funnel runs on.
  • Stand up the commercial stack. Own the CRM as the single source of truth pipeline hygiene, forecast discipline, and the metrics that matter for each motion. Build a revenue picture the CEO and board can underwrite and trust.
  • Define revenue operations. Own the connection between what is promised and what the clinic can deliver and close the loop between demand generation and pipeline so no opportunity is lost in translation.
  • Connect revenue to marketing and clinic operations. Ensure the demand generated on the D2C side feeds cleanly into the pipeline, and that every commitment made in a sale is one the clinical team can fulfil.
• Carry the bag the player
  • Close founding revenue. Personally own and close the first material B2B accounts: employers, advisors, and benefits intermediaries and land the founding D2C membership cohort. You hold a number from day one.
  • Run founder‑led selling. Partner with the founding team on the highest‑value relationships, where the sale turns on trust in the principals, and systematise that motion so it scales beyond the founders.
  • Run both funnels end to end: source, qualify, present, negotiate, and close. Understand the difference between an enterprise B2B cycle and a shorter, higher‑velocity D2C funnel, and run each on its own terms.
  • Build the pipeline from zero. Identify, prospect, and develop relationships across corporate HR and total‑rewards leaders, benefits advisors, family offices, and high‑net‑worth channels creating a pipeline that is not dependent on inbound alone.
• Lead the team the coach
  • Manage and develop the existing commercial team: a Sales Director and Account Executive setting clear expectations, providing regular coaching, and holding the team to the same standards you hold yourself.
  • Hire behind proof. Define the next commercial hires once the motion is demonstrably repeatable, and build the team in step with proven demand not projected demand.
  • Create an environment where the commercial team is measurably more productive with you in the seat than without it through better process, sharper qualification, and honest coaching.

First 12 Months: What Success Looks Like

• A revenue motion that exists and works: founding B2B accounts and the founding D2C membership cohort signed, against targets agreed with the CEO at hire.
• A documented, repeatable playbook for each motion—pricing, funnel, qualification, and forecast—that a recent hire can run with minimal ramp time.
• A clean, trusted pipeline and forecast the board can underwrite.
• A Sales Director and Account Executive who are measurably more productive at month twelve than at your start.
• A credible, costed plan to scale the commercial function to a second site.

Qualifications & Experience

• Must have
  • A closer, first. You have personally carried and beaten a quota recently, not someone whose last few years were spent exclusively in management. The appetite to sell is still genuine, not nostalgic.
  • Proven track record in a complex, relationship‑led, considered‑purchase sale ideally in healthcare, executive benefits, insurance, professional services, or another trust‑based, high‑consideration category where the sale takes time and earns the right to close.
  • Experience running two distinct commercial motions simultaneously: an enterprise or employer‑facing B2B cycle alongside a consumer or direct membership funnel and clear‑eyed clarity about how they differ.
  • Has built the fundamentals from scratch in an early‑stage or greenfield setting: playbook, pipeline discipline, forecast, and CRM infrastructure not only inherited a running commercial machine.
  • A genuine player/coach: energised by closing and by lifting a small team, and not expecting to step back from selling when the first hires are made.
• Strong assets
  • An existing network among Canadian employers, HR and total‑rewards leaders, group benefits advisors, or family‑office and HNW channels.
  • Exposure to both B2B and D2C revenue motions within the same role or organization.
  • Fluency with CRM and a modern commercial stack — able to configure it from scratch, not just operate within an existing setup.
  • Experience in private healthcare, executive health, wellness, or a premium membership model.
  • Bilingualism (French/English) is an asset for the Quebec market as Stem Health expands.

Ideal Candidate

You are a commercially excellent operator who has done this before — built a revenue engine from near‑zero in a category where trust drives conversion, and built it by selling, not by building decks about selling. You are equally energised by landing a complex B2B account and by perfecting the messaging that converts a discerning individual into a founding member. You are rigorous about process, honest about pipeline, and direct in your leadership. You understand that in a founding commercial role, the playbook you write is the one you had to live first — and you would not have it any other way.

Why Join Stem Health

• The founding commercial seat at a physician‑led, membership‑based executive health clinic opening at one of Canada’s most prestigious addresses First Canadian Place in September 2026.
• Real ownership: you define the revenue model, build the commercial stack, write the playbook, and set the standard. Nothing is inherited and nothing is handed down; it is yours to build.
• A product genuinely worth selling: time‑rich, physician‑led care for people who have rarely experienced what great primary care actually feels like.
• An explicit escalator: establish the motion, prove it, and the scope and title grow into full revenue leadership multi‑site, broader team, CRO trajectory.
• Significant variable compensation tied directly to what you close and build not to headcount managed or decks delivered.