VP, Senior Living Sales

. Own new bookings for the Senior Living business unit and stand up the go-to-market engine .

Posted 9/25/2026full-timeRemote • CanadaSeniorWebsite

Key responsibilities & impact

Own new bookings for the Senior Living business unit and stand up the go-to-market engine
Partner with the SVP & GM to segment the market and define coverage
Recruit, onboard, and ramp a national team of Enterprise and Regional sellers
Defend and grow the existing Enterprise customer base while building Regional volume
Run weekly forecast and pipeline inspection, coverage modeling, and accurate commits
Personally engage in top strategic opportunities to remove risk and accelerate sales cycles
Design territories, quotas, CRM structure, forecasting cadence, and reporting infrastructure
Build, codify, measure, and iterate sales processes, qualification standards, playbooks, and deal strategies
Manage legacy-to-new product migration conversations alongside new-logo pipeline
Define and enforce a five-star prospect experience, including SLAs, discovery, demos, business cases, and handoffs
Lead Enterprise and Regional Account Executives through 1:1s, deal strategy sessions, feedback, and performance management
Collaborate cross-functionally on pipeline generation, deal support, implementation confidence, forecasting, upsell, and cross-sell
Build relationships with institutional ownership groups such as REITs and private equity operators
Represent Senior Living at tradeshows, industry summits, and speaking engagements
Track market trends, competitor moves, and win/loss themes
Implement AI-first sales use cases including account research, personalization, call and deal intelligence, and forecasting

What you’ll need

10+ years in healthcare IT or SaaS sales to provider organizations, including senior living, post-acute, health systems, or large ambulatory groups
Consistent record of exceeding quota, including experience competing against better-funded or better-staffed competitors
4+ years leading sales teams, with a record of meeting or exceeding bookings objectives and developing sellers
Demonstrated success building from scratch in a start-up, carve-out, or transformation environment
Ability to recruit, onboard, and rapidly ramp quota-carrying Enterprise and regional sellers
Bias for action and comfort with ambiguity
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 equivalent
Ability to turn pipeline data into executive-ready narratives
Willingness and ability to travel 60%+
Direct senior living market experience and established operator and industry relationships preferred
Experience standing up a new business unit, segment, or go-to-market motion preferred
Experience building relationships with REITs and private equity institutional owners preferred
Experience embedding MEDDICC, Challenger, or Miller Heiman Strategic Selling preferred
Experience applying AI tools to sales workflows preferred

Comp & perks