Senior Vice President & General Manager, Senior Living

Role overview

PointClickCare is hiring a senior executive to lead its Senior Living business as Senior Vice President & General Manager. Reporting to the Chief Revenue Officer, this person will be the single owner of growth, profitability, and market direction for the Senior Living segment, and will oversee the complete customer journey from pipeline creation through retention and expansion.

This is a highly visible, customer-facing leadership role that requires extensive industry knowledge, strong operating instincts, and the ability to build alignment across product, engineering, marketing, and commercial teams. The role is expected to spend substantial time in the market with customers and prospects, building trusted executive relationships and representing PointClickCare across the Senior Living landscape.

Work location and travel expectations

The role is listed as Mississauga-Hybrid / Canada-Remote. For remote arrangements, in-person travel will still be required for onboarding, team events, and semi-annual and annual meetings at the Mississauga and/or Salt Lake City office. For hybrid arrangements, candidates must live within commuting distance of the stated office location and should expect regular office attendance for team-based events. This requirement applies to the position.

About PointClickCare

PointClickCare is a founder-led, privately held health technology company focused on helping care providers deliver excellent care. Its platform supports more than 30,000 provider organizations and is backed by the largest long-term and post-acute care dataset along with a marketplace of 400+ integrated partners. The company reinvests heavily in research and development and promotes a workplace centered on innovation, flexibility, growth, and meaningful impact.

The organization also emphasizes the use of AI as a tool to support creativity, productivity, and better decision-making, and it actively looks for candidates whose AI fluency can complement its mission.

What you will own

• Set the strategy for the Senior Living segment, with tailored go-to-market approaches for diversified operators and pure-play Senior Living organizations.
• Act as the executive sponsor for major customers and prospects, spending meaningful time in market to strengthen credibility and trust.
• Represent the company at industry events, conferences, and advisory boards to help shape market perception and competitive positioning.
• Work with the CRO and executive leadership on annual planning, budget allocation, and investment priorities for the vertical.
• Own the Senior Living P&L, including revenue, gross margin, and operating expense responsibility across all relevant market segments.
• Lead growth across net new ARR, retention, and expansion revenue, while maintaining strong pipeline management and forecast discipline.
• Build and execute segment-specific investment plans that reflect the needs of independent living, assisted living, memory care, and continuing care retirement communities.
• Evaluate inorganic growth opportunities such as partnerships and adjacent-market expansion in collaboration with strategy and corporate development partners.
• Lead the go-to-market motion for Senior Living products across all segments.
• Directly manage customer-facing functions, including Sales, Customer Success, Professional Services, and Support leadership.
• Hire, develop, and retain high-performing talent and build a team capable of delivering aggressive growth while maintaining an excellent customer experience.
• Guide cross-functional teams and matrixed resources toward shared business goals.
• Create performance expectations, accountability systems, and career development paths for the customer-facing organization.
• Ensure staffing and capability plans are in place to support current and future Senior Living investments.
• Provide matrix leadership to Marketing, Product Management, and Engineering so roadmaps and campaigns stay aligned with segment priorities.
• Serve as the primary customer voice into product planning so feature priorities reflect market needs and competitive gaps.
• Partner with Marketing on demand generation, content, and positioning specific to Senior Living buyers.
• Collaborate with Finance, Legal, and People & Culture to ensure operational execution meets company requirements and standards.

Required background and qualifications

• At least 15 years of progressive leadership experience in enterprise software, healthcare technology, or a similar SaaS environment, including 5+ years in a senior executive role with P&L ownership.
• Strong understanding of the Senior Living market, including operator economics, care models, regulation, and the technology ecosystem.
• Proven record of scaling customer-facing teams in a fast-growing B2B software company.
• Ability to influence outcomes across product, engineering, and marketing in a matrixed organization without relying on direct authority.
• Experience developing executive-level customer relationships and engaging credibly with C-suite leaders.
• Solid financial understanding, including ownership of a multi-million-dollar P&L and SaaS performance metrics.
• Willingness and ability to travel extensively to meet customers, prospects, and team members across key markets.

Preferred leadership qualities

• Strong executive presence and the confidence to represent the business at senior levels.
• A collaborative leadership style that builds trust through transparency, shared goals, and a team-first mindset.
• Ability to analyze market trends, competition, and customer insight to turn complexity into clear strategy.
• Deep customer orientation and a genuine interest in improving care outcomes and operational performance.
• A track record of developing people and creating environments where talented employees want to stay and grow.
• Comfort working in fast-moving, ambiguous settings and making sound decisions with incomplete information.
• Familiarity with the different business models and buying behaviors of diversified post-acute operators and pure-play Senior Living organizations.

Compensation and benefits

The Canada base salary for this role is part of a broader total rewards package that includes a competitive base salary, bonus, and benefits. Compensation is determined by job level, relevant skills, experience, and work location. The recruiter can provide additional details during the hiring process.

• Benefits starting on day 1
• Retirement plan matching for RRSP and 401K
• Flexible paid time off
• Lifestyle and wellness spending account
• Parental and caregiver leave
• Fertility and adoption support
• Continuous development support program
• Employee assistance program
• Learning programs and resources
• Employee recognition and more

Equal opportunity and hiring notes

PointClickCare is committed to equal employment opportunity and does not discriminate on protected grounds such as race, religion, national origin, age, sex, sexual orientation, gender identity or expression, marital or civil partnership status, disability, veteran status, genetic information, or any other legally protected characteristic. The company welcomes applicants with disabilities and will provide accommodations upon request during the selection process.

Applicant information is processed and stored with Lever and may be retained for consideration for future roles in line with privacy and retention practices. The company also states that it is committed to information security, and anyone hired must follow its security policies and procedures to protect confidential and sensitive information.

The hiring process may involve AI tools to assist with reviewing applications, analyzing resumes, or checking responses for inconsistencies or verification signals. These tools support the recruitment team, while final hiring decisions remain human-led.