Senior Vice President & General Manager Senior Living

Job Title: Senior Vice President & General Manager, Senior Living

Location: Mississauga-Hybrid / Canada-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.

For Hybrid Roles: If this role is Hybrid, there will be an expectation to reside within commutable distance to the office/location specified in the job listing. This will include, but not limited to, weekly/bi-weekly/monthly events in the office with your specific team. This is a requirement for this role.

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.

Position Summary

PointClickCare is seeking a seasoned executive to serve as Senior Vice President & General Manager, Senior Living. Reporting directly to the Chief Revenue Officer, this role is the single accountable executive for all growth, profitability, and market strategy within the Senior Living vertical. The SVP & GM owns the full customer lifecycle — from pipeline and acquisition through retention and expansion — and acts as the face of PointClickCare to the Senior Living market.

This is a highly visible, field-oriented executive role that demands deep industry expertise, an operator’s mindset, and a collaborative leadership style. The SVP & GM will spend significant time in market and with customers, building trusted relationships with C-suite stakeholders at both diversified and pure-play Senior Living operators. Success in this role requires the ability to lead through influence as well as authority, aligning product, engineering, and marketing partners around a shared Senior Living strategy.

Key Responsibilities

Strategic Leadership & Market Ownership

• Define and own the Senior Living segment strategy, including distinct go-to-market approaches for diversified operators and pure-play Senior Living organizations.
• Serve as the primary executive sponsor and relationship owner for key Senior Living customers and prospects, spending substantial time in market to deepen industry credibility and customer trust.
• Represent PointClickCare at senior industry forums, conferences, and customer advisory boards, shaping market perception and competitive positioning.
• Collaborate with the CRO and the broader executive team on annual planning, resource allocation, and investment priorities for the Senior Living vertical.
  
  

P&L Management & Revenue Growth

• Own the P&L for the Senior Living business unit, including revenue, gross margin, and operating expense accountability across all SL market segments.
• Drive net new ARR growth, net revenue retention, and expansion revenue targets, maintaining rigorous pipeline discipline and forecast accuracy.
• Develop and execute segment-specific investment theses, ensuring resource allocation reflects the distinct dynamics of independent living, assisted living, memory care, and continuing care retirement communities.
• Identify and pursue inorganic growth opportunities, including partnerships and adjacent market expansion, in coordination with Strategy, Partnerships, and Corporate Development.
  
  

Customer-Facing Team Leadership

• Drive the full go-to-market motion for all Senior Living Products across all segments.
• Hold direct line management responsibility for all customer-facing functions within the Senior Living vertical, including Sales, Customer Success, Professional Services, and Support leadership.
• Recruit, develop, and retain top talent, building a high-performance team capable of executing against aggressive growth targets while delivering an outstanding customer experience.
• Operate, manage, and lead a cross functional team of direct reports and matrixed resources to achieve jointly established business objectives.
• Establish clear performance standards, accountability frameworks, and career development pathways across the customer-facing organization.
• Ensure appropriate staffing levels and skills to support current and planned Senior Living investments, proactively identifying and closing talent gaps.
  
  

Cross-Functional Partnership

• Exercise matrixed leadership over Marketing, Product Management, and Engineering resources aligned to the Senior Living vertical, aligning roadmaps and campaigns to segment priorities.
• Act as the primary voice of the Senior Living customer into the product organization, ensuring feature prioritization reflects validated market needs and competitive gaps.
• Partner with Marketing to develop Senior Living-specific demand generation strategies, content, and brand positioning that resonate with operator buyers.
• Collaborate closely with Finance, Legal, and People & Culture to align operational execution with corporate standards and requirements.
  
  

Required Skills & Qualifications

• 15+ years of progressive leadership experience in enterprise software, healthcare technology, or a related SaaS environment, with at least 5 years in a senior executive role with P&L ownership.
• Deep knowledge of the Senior Living market, including operator economics, care delivery models, regulatory environment, and the technology landscape serving the sector.
• Demonstrated success leading and scaling customer-facing organizations (Sales, CS, Services) in a high-growth B2B software company.
• Proven ability to operate effectively in a matrixed environment, influencing outcomes across product, engineering, and marketing without direct authority.
• Track record of building and maintaining executive-level customer relationships, with the credibility to engage as a peer with C-suite leaders at major Senior Living operators.
• Strong financial acumen, including experience owning and managing a multi-million dollar P&L, with proficiency in SaaS revenue metrics and operating KPIs.
• Willingness and ability to travel extensively to be present with customers, prospects, and team members across key markets.
  
  

Preferred Experience

• Executive Presence & Influence. Ability to command a room, inspire confidence with customers and colleagues alike, and represent PointClickCare with authority and authenticity at the highest organizational levels.
• Collaborative Leadership Style. Highly consultative approach to cross-functional partnership; earns trust and drives alignment through transparency, shared goals, and a genuine commitment to collective success over individual credit.
• Strategic & Analytical Thinking. Capacity to synthesize complex market dynamics, competitive data, and customer insights into clear strategic choices and actionable plans.
• Customer Obsession. Genuine passion for the Senior Living sector and its mission; deeply curious about operator challenges and motivated by delivering technology that improves care outcomes and operational performance.
• Talent Development. A reputation as a developer of people; known for building diverse, high-performing teams and creating environments where top talent chooses to stay and grow.
• Adaptability & Resilience. Thrives in fast-paced, evolving environments; comfortable operating with ambiguity and making sound decisions with imperfect information.
• Segment Fluency. Familiarity with the distinct business models and buying dynamics of both diversified post-acute operators with Senior Living assets and pure-play Senior Living organizations; able to tailor strategy and message accordingly.
  
  

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

It is the policy of PointClickCare to ensure equal employment opportunity without discrimination or harassment on the basis of race, religion, national origin, status, age, sex, sexual orientation, gender identity or expression, marital or domestic/civil partnership status, disability, veteran status, genetic information, or any other basis protected by law. PointClickCare welcomes and encourages applications from people with disabilities. Accommodations are available upon request for candidates taking part in all aspects of the selection process. Please contact [email protected] should you require any accommodations.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, or if you would like to ask to access, correct, or delete your information, please contact PointClickCare’s human resources team: [email protected]

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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Location: Mississauga, Mississauga, Ontario, Canada