Director of Sales

Stem Health; Toronto; On-site; CAD 150,000 - 230,000; Full time

Job summary

Stem Health is launching a physician-led, membership-based primary care model at First Canadian Place in Toronto. We seek a dynamic Director of Sales to own both D2C and B2B motions, close founding revenue, and build scalable processes with a hands-on, coaching approach.

You will architect the sales motion, stand up the CRM, and deliver repeatable playbooks while collaborating with clinical and operations teams to ensure feasible handoffs and strong renewal foundations.

Qualifications

• Must have closed deals recently and not only reviewed pipelines.
• Proven track record in complex, relationship-led sales in healthcare or premium membership.
• Experience running a B2B corporate cycle alongside a consumer funnel.
• Built a sales motion from scratch in an early-stage setting.
• Bilingualism (French/English) is an asset.

Responsibilities

• Own both B2B and D2C sales funnels end to end with repeatable playbooks.
• Stand up CRM as the single source of truth with accurate forecasting.
• Develop sales collateral and pricing decks for new hires.
• Close the first cohorts and ensure handoffs to operations are feasible.
• Coach and recruit to scale the commercial team.

Skills

Closing deals

CRM setup

B2B sales

Healthcare sales

Executive benefits

Tools

CRM systems

Job description

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. We offer individual, family, and corporate memberships, with a care model built on time, trust, and exceptional service.

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. We offer individual, family, and corporate memberships, with a care model built on time, trust, and exceptional service.

The Mandate

Stem Health sells membership across two channels: a direct-to-consumer (D2C) individual and family membership, and a B2B corporate programme sold to employers and through benefits advisers. Both are live from day one. As Director of Sales, you carry both and you carry them by selling, not by managing from a distance.

This is not a role for someone who last held a bag three years ago. It is for a closer who still loves the work, who can run a complex employer cycle and a shorter consumer funnel simultaneously, and who understands that in an early-stage membership business the most valuable thing you can do is personally close the first cohorts, learn what actually converts, and lock that into a system. The role grows as the motion is proven.

What You Will Own

Build the sales motion - the architect

• Own both sales funnels end to end. Define the qualification criteria, stage definitions, objection-handling, and closing cadence for the B2B corporate motion and the D2C individual membership motion and write them down so they are repeatable without you.
• Stand up and own the CRM as the single source of truth. Pipeline hygiene, stage accuracy, forecast discipline, and the metrics the CEO can rely on built from scratch, not inherited.
• Develop the sales collateral. Proposals, one-pagers, objection guides, pricing decks the materials a prospect needs to say yes, and a new hire needs to run the motion without reinventing it.
• Close the loop between sales and operations. Every commitment made in a sale must be one the clinical and operations team can fulfil. Own that handoff and own what breaks when it does not work.
  

Carry the bag - the player

• Close founding revenue. Personally own and close the first B2B corporate accounts employers, HR and total-rewards leaders, benefits advisers, building tenants at First Canadian Place and land the founding D2C membership cohort. You hold a number from day one.
  
• Run both funnels end to end source, qualify, present, negotiate, close. Understand that a six-week employer cycle and a two-call individual membership conversion are different animals, and run each accordingly.
  
• Build the pipeline from zero. Prospect and develop relationships across corporate HR, group benefits advisors, family offices, and high-net-worth channels. The pipeline you build must not be dependent on inbound alone.
  
• Treat retention as a sales motion, not an operational afterthought. Own renewal conversations, track churn risk early, and close the members who are drifting before they leave.
  

Lead and develop - the coach

• Set clear expectations for any commercial team members you manage targets, pipeline standards, call quality, and follow-up discipline and hold the bar you set for yourself.
  
• Coach on what actually closes. Share what you learn in the field and build a team that gets sharper over time, not one that operates on intuition alone.
  
• Hire behind proof. Define the next commercial hire once the motion is demonstrably repeatable, and grow the team in step with demand not ahead of it.
  

First 12 Months: What Success Looks Like

• Founding B2B corporate accounts signed and onboarded, and a D2C founding membership cohort closed against targets agreed with the CEO at hire.
  
• A documented, repeatable sales playbook for both motions funnel, qualification, objection handling, and forecast that a new hire can run with minimal ramp time.
  
• A clean, trusted CRM and pipeline that the CEO can read and rely on without asking for an explanation.
  
• Renewal rate and churn tracked as commercial metrics, with a structured renewal process in place before the first member anniversaries arrive.
  
• A credible, costed case for the next sales hire, grounded in what the proven motion can absorb.
  

Qualifications & Experience

Must have

• A closer, first. You have personally carried and beaten a quota recently not someone whose last few years were spent in pipeline reviews and team meetings. The appetite to sell is genuine, not nostalgic.
  
• Proven track record in a complex, relationship-led, considered-purchase sale in healthcare, executive benefits, insurance, professional services, premium membership, or another high-trust category where the sale takes time and earns the right to close.
  
• Experience running a B2B employer or corporate cycle alongside a consumer or direct membership funnel and clear-eyed clarity about how the two differ in cadence, stakeholder dynamics, and close mechanics.
  
• Has built the sales fundamentals from scratch in an early-stage or greenfield setting: playbook, pipeline discipline, CRM from zero not only operated within an existing commercial machine.
  
• A genuine player-coach: energised by closing deals and by lifting the people around them, and not expecting to step back from selling when a first hire is made.
  

Strong assets

• An existing network among Canadian corporate HR and total-rewards leaders, group benefits advisers, or family-office and HNW channels.
  
• Experience in private healthcare, executive health, wellness, or a premium membership model.
  
• Fluency with CRM able to configure it from scratch, enforce hygiene across a team, and build the reports that matter.
  
• Exposure to both B2B and D2C revenue motions within the same role or organization.
  
• Bilingualism (French/English) is an asset as Stem Health expands.
  

Ideal Candidate

You are commercially sharp, personally credible, and genuinely motivated by closing not by the idea of closing. You can run a six-week employer sales cycle and convert a high-net-worth individual in two calls, and you understand why those are different conversations. You are rigorous about pipeline, honest about what is stalling, and direct in your coaching. You have built a sales motion from scratch before, and you know that the playbook only works if you lived it first. You want to sell something worth selling and at Stem Health, you will.

Why Join Stem Health

• Own the sales function at a physician-led, membership-based clinic at First Canadian Place a ground-floor commercial seat, opening September 2026.
• Sell something genuinely worth selling: time-rich, physician-led care for people who have rarely experienced what great primary care actually feels like.
• Report directly to the CEO with a clear mandate, real commercial authority, and a clinical and operations team that delivers on every promise you make in the field.
• Significant variable compensation tied directly to what you close not to headcount managed or decks delivered.
• An explicit growth path: prove the motion, and the scope and seniority grow with it.