VP, Senior Living Sales

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take ownership of new bookings for the Senior Living business unit and establish the go-to-market strategy.

• Collaborate with the SVP & GM to segment the market and determine coverage.

• Recruit, onboard, and rapidly develop a national team of Enterprise and Regional sales professionals.

• Protect and expand the existing Enterprise customer base while enhancing Regional volume.

• Conduct weekly forecasts and pipeline inspections, coverage modeling, and accurate commitments.

• Personally engage in key strategic opportunities to mitigate risk and expedite sales cycles.

• Design territories, quotas, CRM structure, forecasting cadence, and reporting systems.

• Create, document, measure, and refine sales processes, qualification standards, playbooks, and deal strategies.

• Oversee conversations regarding legacy-to-new product migration in conjunction with the new-logo pipeline.

• Define and uphold a five-star prospect experience, which includes SLAs, discovery, demos, business cases, and handoffs.

• Guide Enterprise and Regional Account Executives through one-on-ones, deal strategy sessions, feedback, and performance management.

• Work collaboratively across functions on pipeline generation, deal support, implementation confidence, forecasting, upselling, and cross-selling.

• Establish relationships with institutional ownership groups such as REITs and private equity operators.

• Represent the Senior Living division at trade shows, industry summits, and speaking engagements.

• Monitor market trends, competitor activities, and win/loss patterns.

• Implement AI-driven sales use cases, including account research, personalization, call and deal intelligence, and forecasting.

⛳️ Requirements

• Over 10 years of experience in healthcare IT or SaaS sales to provider organizations, including senior living, post-acute care, health systems, or large ambulatory groups.

• Proven track record of exceeding quotas, including experience competing against better-funded or better-staffed competitors.

• At least 4 years of experience leading sales teams, with a history of meeting or surpassing bookings objectives and developing sales talent.

• Demonstrated success in building from the ground up in a startup, carve-out, or transformative environment.

• Ability to recruit, onboard, and quickly ramp quota-carrying Enterprise and Regional sellers.

• Proactive mindset and comfort with ambiguity.

• Experience in cross-functional collaboration with Marketing, Sales Development, Solution Design, Professional Services, Customer Success, Revenue Operations, and Data Science.

• Strong forecasting and CRM discipline using Salesforce or similar tools.

• Capacity to convert pipeline data into narratives suitable for executive presentation.

• Willingness and ability to travel over 60% of the time.

• Direct experience in the senior living market and established relationships with operators and industry stakeholders preferred.

• Experience in launching a new business unit, segment, or go-to-market strategy preferred.

• Familiarity with building relationships with REITs and institutional private equity owners preferred.

• Experience implementing MEDDICC, Challenger, or Miller Heiman Strategic Selling frameworks preferred.

• Prior experience in applying AI tools to sales processes preferred.

🏝️ Benefits

• Benefits commence from Day 1.

• Retirement Plan Matching (RRSP & 401K).

• Flexible Paid Time Off.

• Lifestyle/Wellness Spending Account.

• Parental & Caregiver Leaves.

• Support for Fertility & Adoption.

• Continuous Development Support Program.

• Employee Assistance Program.

• Access to Learning Programs & Resources.

• Employee Recognition initiatives.

• Competitive base salary along with commission and benefits.