VP, Senior Living Sales

Job Title: VP, Senior Living Sales Location: USA – Remote **Travel to Office expectations** For Remote Roles : If this role is remote, there will be in-office events that will require travel to and from the Mississauga and/or Salt Lake City office. These will include, but not limited to, onboarding, team events, semi-annual and annual team meetings. At PointClickCare our mission is simple: to help providers deliver exceptional care. And that starts with our people. As a leading health tech company that’s founder-led and privately held, we empower our employees to push boundaries, innovate, and shape the future of healthcare. With the largest long-term and post-acute care dataset and a Marketplace of 400+ integrated partners, our platform serves over 30,000 provider organizations, making a real difference in millions of lives. We also reinvest a significant percentage of our revenue back into research and development, ensuring our employees have the resources to innovate and make a lasting impact. Recognized by Forbes as a top private cloud company and honored as one of Canada’s Most Admired Corporate Cultures, we offer flexibility, growth opportunities, and meaningful work.  At PointClickCare, we empower our people to be the architects of a smarter healthcare future; one that is human-first and accelerated by AI to create meaningful and lasting change. Employees harness AI as a catalyst for creativity, productivity, and thoughtful decision-making. By integrating AI tools into our daily workflows, collaboration is enhanced, outcomes are improved, and every team member has the proficiency to maximize their impact. It all starts with our hiring practices where we uncover AI expertise that complements our mission, and we continue to invest in training and development to nurture innovation throughout the employee journey. Join us in redefining healthcare — so it doesn’t just survive, it thrives. To learn more about PointClickCare, check out  Life at PointClickCare  and connect with us on  Glassdoor  and  LinkedIn . About the Team Senior Living represents a rare opportunity to build a business within an established market leader. As a newly carved-out business unit, it is actively defining the strategy, operating model, and commercial approach needed to win in the senior living market. This includes shaping everything from segmentation and coverage design to the core sales infrastructure, including forecasting, compensation, deal support, and data processes, creating the foundation required to scale the business over time. The team is fully remote and national, and will scale quickly to include Enterprise and Regional sellers supported by dedicated Marketing, Sales Development, Solution Design, Professional Services, Customer Success, Revenue Operations, and Data Science partners. For a builder, this is a rare opportunity to design a business unit's commercial engine from day one, with the brand, data, and customer base of an established leader behind it. Position Summary: The VP, Senior Living Sales owns new bookings for the Senior Living business unit and is accountable for standing up the go-to-market engine that delivers them. This role exists because the senior living market requires a dedicated, purpose-built sales motion designed specifically for how senior living operators buy. Senior Living has been identified by company leadership as the business unit most in need of increased focus and investment, following several years of declining bookings and a market position behind better-resourced competitors — this VP is accountable for reversing that trajectory as much as for building new capability. Reporting to the SVP & GM, Senior Living, this leader partners with the GM to segment the market, define coverage, and rapidly recruit a national team of Enterprise and Regional sellers, while personally engaging in the largest strategic opportunities. Because the Enterprise segment carries both the greatest growth opportunity and the business's most pressing retention risk, this leader must defend and grow the existing Enterprise base at the same time as building new Regional volume. This VP will build and manage a team of Enterprise and Regional Account Executives. Speed and quality are the operating standard. This is a builder's role for a start-up-minded leader who moves with urgency, sets the bar for a five-star prospect experience in the earliest stages of the buying process, and creates process where none exists rather than waiting for it. Success depends as much on grit, ownership, and cross-functional collaboration as on traditional sales leadership — this leader takes on whatever the business needs to win and expects the same of the team. Because the Senior Living platform is still being consolidated and built out, this leader must also be equipped to sell a migration story to existing customers on legacy products, in parallel with a new-logo pitch to prospects. Key Responsibilities: Build the team. Partner with the SVP & GM to define the coverage model, then recruit, onboard, and ramp a national team of Enterprise and Regional sellers — two distinct commercial motions requiring different territory design, quota structure, and deal cycles. Set a high talent bar, hire ahead of need, and compress time-to-first-deal through structured onboarding, certification, and hands-on early deal support, while stabilizing retention and performance on the existing Enterprise seller base. Own the number. Carry full accountability for Senior Living new bookings. Run a disciplined forecast and pipeline cadence — weekly inspection, coverage modeling, and accurate commits — and stay personally engaged in top strategic opportunities to remove risk and accelerate cycles. Build the go-to-market motion. Work with the SVP & GM, Revenue Operations, Marketing and Data Science to segment the market, design territories and quotas, align coverage with core team sellers, an