Senior Vice President & General Manager, Senior Living

PointClickCare•Mississauga, ON

7d•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.