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, and build the forecasting cadence, CRM structure, and reporting infrastructure this business needs. Build the sales process, qualification standards, playbooks, and deal strategies this market requires — then codify, measure, and iterate them quickly rather than waiting for a finished model. This includes equipping the team to sell effectively while the underlying platform is still being consolidated, managing legacy-to-new migration conversations alongside new-logo pipeline.
• Set the standard for the buyer experience. Define and enforce a five-star prospect experience through the early buying stages: response-time SLAs, executive-caliber discovery, tailored demos and business cases, and a handoff to Solution Design and Professional Services that never asks the prospect to repeat themselves.
• Lead a team of Enterprise and Regional Account Executives and lead in market. Spend the majority of time in market with AE’s and prospects on top strategic opportunities. Run weekly 1:1s and deal strategy sessions, set clear performance expectations, give direct and timely feedback, manage performance decisively, and build a culture of urgency, grit, and continuous improvement.
• Drive cross-functional alignment. Partner with Marketing and SDRs on pipeline generation, Solution Design on deal support, Professional Services on scoping and implementation confidence, Revenue Operations and Data Science on forecasting and reporting infrastructure, and Customer Success, Partnerships, and Senior Care on upsell and cross-sell — creating one seamless customer journey from first touch through go-live. As ownership of senior living communities continues to consolidate under REITs and private equity operators, this also includes building relationships with institutional ownership groups that increasingly influence purchasing decisions across their portfolios.
• Represent Senior Living in the market. Serve as a visible face of the business at tradeshows, industry summits, and speaking engagements. Track market trends, competitor moves, and win/loss themes, and channel that intelligence back to Product, Marketing, and the GM to sharpen strategy and messaging.
• Operate AI-first. Translate business unit AI direction into a prioritized set of sales use cases — account research, personalization, call and deal intelligence, forecasting — and embed adoption, governance, and measurable outcomes into the team's daily workflow.

Required Skills & Qualifications:

• 10+ years in healthcare IT or SaaS sales to provider organizations — senior living, post-acute, health systems, or large ambulatory groups — with a consistent record of exceeding quota, including experience competing against better-funded or better-staffed competitors and winning on execution and relationships
• 4+ years leading sales teams, with a proven record of meeting or exceeding bookings objectives and developing sellers
• Demonstrated success building from scratch — a new team, territory, segment, or business unit — in a start-up, carve-out, or transformation environment
• Proven ability to recruit, onboard, and ramp quota-carrying Enterprise and regional sellers quickly, with evidence of ramp velocity and retention
• Bias for action and comfort with ambiguity — builds process, playbooks, and structure where none exists instead of waiting for direction
• Demonstrated cross-functional collaboration with Marketing, Sales Development, Solution Design, Professional Services, Customer Success, Revenue Operations, and Data Science, with an owner's mindset and no “that's not my job”
• Strong forecasting and CRM discipline (Salesforce or equivalent), with the ability to turn pipeline data into executive-ready narratives; willing and able to travel 60%+

Preferred Experience:

• Direct experience in the senior living market (independent living, assisted living, memory care), with established operator and industry relationships
• Experience standing up a new business unit, segment, or go-to-market motion inside a larger, established organization, including building relationships with institutional owners (REITs, private equity) as a distinct buying influence
• Experience embedding a formal sales methodology (e.g., MEDDICC, Challenger, or Miller Heiman Strategic Selling) into a newly formed team
• Experience applying AI tools to accelerate research, personalization, deal inspection, and forecast accuracy

At PointClickCare, base salary is one of the many components that make up our total rewards package. This role offers a competitive base salary+ commission + benefits, non-overtime eligible. Our salary ranges are determined by job and level. Within the range, individual compensation is determined by job-related skills and knowledge, relevant experience including professional and lived experience, and/or work location. Your recruiter can share more information about our total rewards package during the hiring process.

PointClickCare Benefits & Perks

• 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 … and more!

Equal Employment Opportunity:

PointClickCare is committed to Information Security. By applying to this position, if hired, you commit to following our information security policies and procedures and making every effort to secure confidential and/or sensitive information.

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