Careers

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Director of Sales

Toronto, ON | Hybrid (Preferred) or Remote Type: Full-time | Comp: $120k–$150k OTE (Year 1)

The Opportunity

We are looking for an ambitious Director of Sales to act as our first full-time sales hire.

This is a high-impact, "player-coach" role. You will work directly with the C-suite to build our sales engine from the ground up. You won’t just be managing a team yet—you will be the engine, responsible for the end-to-end sales cycle, from cold outreach to contract signature.

You will target Long-Term Care (LTC) and Retirement Homes across Canada, with a view toward US expansion by Q4 2026. If you are a hunter who loves the thrill of the close but also has the strategic vision to build a department, this is your home.

What You'll Do

1. Sales Strategy & Execution (80%)

Own the Funnel: Manage the full sales pipeline from prospecting to close. You are responsible for generating leads, conducting cold/warm outreach, and securing contracts.
The Pitch: Deliver high-impact product demos (virtual and in-person) to Executive Directors, Directors of Recreation and other decision-makers in the Senior Living sector.
The Strategy: Codify our sales process. You will test scripts, identify objection handling techniques, and build the playbook for future hires.
Market Presence: Represent caregiVR at 2–4 major senior care conferences annually to drive brand awareness and fill the top of the funnel.

2. Account Growth & Operations (20%)

Renewal & Retention: Partner with the Director of Customer Success to ensure seamless handoffs, successful launches, and contract renewals.
Feedback Loop: Act as the voice of the customer. Synthesize market feedback to help the CEO and leadership team refine product offerings and marketing collateral.
Operational Agility: Assist with the logistical side of closing deals (contracts, invoicing) and occasionally support the testing of equipment to ensure your demos run flawlessly.
Teamwork: As a core team member of an early stage startup, you will be responsible for being a key voice in weekly team meetings, quarterly strategy meets, and annual team retreats. You may also be asked to support team members in their projects for “all hands on deck” moments.

First 12 weeks (key deliverables)

Build the Pipe: Establish a lead funnel with at least 30 qualified leads.
Engage: Conduct introduction/discovery calls with at least 10 existing customers to understand the "why" behind their purchase.
Process: Develop and document a repeatable sales process based on your early observations.
Results: Close 2+ new sales with LTC or Retirement homes.

Who You Are

A Hunter: You are not afraid of cold calling, LinkedIn outreach, or hearing "no." You possess the grit required to build a pipeline from scratch.
Sector Experienced: You ideally have experience selling technology or services to LTC, Senior Living, or Healthcare organizations. You understand the nuances of the procurement cycle in this industry, and key contacts within the space.
A Builder: You are comfortable working in a fast-paced, unstructured startup environment where you must build the road as you drive on it.
Analytically Minded: You can look at data and tell us why a deal stalled or why a campaign worked.

What We Offer

Compensation: Competitive Base + Commission with a Year 1 OTE (On-Target Earnings) of $120,000–$150,000.
Growth: This is a strategic role. You will have the opportunity to shape the company's future and build a sales team under you as we scale.
Flexibility: Hybrid work environment (Toronto preferred) that respects how you deliver results best.
Impact: Work on a product that genuinely improves the lives of seniors and their caregivers.

How to Apply

Upload your cover letter and CV using the form below
Tip: Don’t be afraid to show off your personality—we’re a fun-loving team and want to know the real you!

Requirements

Authorized to work in Canada
3+ years of experience in Sales