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About the role

  • VP leading PointClickCare’s senior living healthcare SaaS sales growth. Building the national sales team, go-to-market motion, and new bookings engine.

Responsibilities

  • 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

Requirements

  • 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

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
  • Competitive base salary plus commission and benefits

Job title

Job type

Full Time

Experience level

Senior

Salary

Not specified

Degree requirement

No Education Requirement

Location requirements

RemoteCanada

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