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About the role
Key responsibilities & impact- Own new bookings for the Senior Living business unit
- Stand up the go-to-market engine and reverse declining bookings
- 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
- Build and manage Enterprise and Regional Account Executives
- 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 response-time SLAs, discovery, tailored demos, business cases, and handoffs
- Lead weekly 1:1s and deal strategy sessions; set expectations, provide feedback, and manage performance
- Partner cross-functionally with Marketing, SDRs, Solution Design, Professional Services, Revenue Operations, Data Science, Customer Success, Partnerships, and Senior Care
- Build relationships with REITs and private equity ownership groups
- Represent Senior Living at tradeshows, industry summits, and speaking engagements
- Track market trends, competitor moves, and win/loss themes
- Apply AI to account research, personalization, call and deal intelligence, and forecasting
Requirements
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 proven 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 ramp quota-carrying Enterprise and regional sellers quickly
- Bias for action and comfort with ambiguity
- Demonstrated 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
- Willing and able 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 institutional owners such as REITs and private equity preferred
- Experience embedding a formal sales methodology such as MEDDICC, Challenger, or Miller Heiman Strategic Selling preferred
- Experience applying AI tools to accelerate research, personalization, deal inspection, and forecast accuracy preferred
Benefits
Comp & perks- Competitive base salary + commission + benefits
- Benefits starting from Day 1
- Retirement Plan Matching (RRSP & 401K)
- Flexible Paid Time Off
- Lifestyle/Wellness Spending Account
- Parental & Caregiver Leaves
- Fertility & Adoption Support
- Continuous Development Support Program
- Employee Assistance Program
- Learning Programs & Resources
- Employee Recognition
- In-office events, including onboarding, team events, and semi-annual and annual team meetings