Vice President, Organizational Change and Enablement (CA)

PointClickCare • Mississauga, Peel • 1d ago

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 [https://can01.safelinks.protection.outlook.com/?url=https%3A%2F%2Fpointclickcare.com%2Flife-at-pointclickcare%2F&data=05%7C02%7CSandeep.Dhillon%40pointclickcare.com%7Ce9353db140a24fd980f808ddb00013f1%7Cafd0249eca3d42058bf4ac2b6abd0fec%7C0%7C0%7C638860236586947941%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=dIKtrMG7L0sb%2FfLrFRvhcZAmfqfNXTXDTvMsoJkwGvM%3D&reserved=0] and connect with us on Glassdoor [https://can01.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.glassdoor.ca%2FOverview%2FWorking-at-PointClickCare-EI_IE452666.11%2C25.htm&data=05%7C02%7CSandeep.Dhillon%40pointclickcare.com%7Ce9353db140a24fd980f808ddb00013f1%7Cafd0249eca3d42058bf4ac2b6abd0fec%7C0%7C0%7C638860236586978442%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=KVgSiL%2ByFmnpxTc5PmuErMwRNwDmTGqUzJIUSIm5fY0%3D&reserved=0]and LinkedIn [https://can01.safelinks.protection.outlook.com/?url=https%3A%2F%2Fwww.linkedin.com%2Fcompany%2Fpointclickcare%2F&data=05%7C02%7CSandeep.Dhillon%40pointclickcare.com%7Ce9353db140a24fd980f808ddb00013f1%7Cafd0249eca3d42058bf4ac2b6abd0fec%7C0%7C0%7C638860236586994867%7CUnknown%7CTWFpbGZsb3d8eyJFbXB0eU1hcGkiOnRydWUsIlYiOiIwLjAuMDAwMCIsIlAiOiJXaW4zMiIsIkFOIjoiTWFpbCIsIldUIjoyfQ%3D%3D%7C0%7C%7C%7C&sdata=AFNWMltUX65iQ5E5LFYOrA9bKP10SzKQ7jwcti57q2E%3D&reserved=0].

Travel to Office expectations

For Remote Roles: As 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: As 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.

Position Summary:

We are seeking a transformational change leader to own, architect, and lead the execution of our enterprise-wide Organizational Capability Roadmap—with a focus on workforce readiness, capability uplift, and AI first culture transformation. Evolving from a traditional OCM role, this position reflects the strategic imperative to embed AI into the fabric of how we work and lead.

This role will be central to building the mindset, muscle, and mechanisms required to scale AI fluency and transformation—across all functions, teams, and leadership levels. The VP, Organizational Change & Enablement will drive strategic adoption of AI tools, behaviors, and decision-making frameworks to power business outcomes.

This leader will partner closely with HR, the Office of Information Management, Product, Technology, and Executive Leadership to ensure our workforce is future-ready, ethically aligned, and strategically equipped to thrive in an AI-enabled enterprise.

Key Responsibilities:

Organizational Capability Roadmap Ownership:
Own and lead the strategic development, implementation, and governance of the Organizational Capability Roadmap.
Partner with HR, functional business leaders and the Office of Information Management (OIM) to embed the roadmap into workforce strategy, enterprise platforms, and operating models.
Ensure alignment between AI strategy and organizational design, talent architecture, and transformation initiatives.
AI Capability Uplift & Fluency Building:
Design and implement an enterprise-wide AI fluency framework progressing employees from Awareness ? Practitioner ? Strategic Integrator.
Develop targeted capability-building journeys for people leaders, business teams, and technical contributors.
Activate and support a network of AI Champions and Internal Coaches to drive local adoption and practice-sharing.
Embed fluency development into existing talent, learning, and performance management systems.
AI-Infused Workforce Planning & Reskilling:
Partner with Talent, L&D, Workforce Planning, and OIM to define future-state roles, skills, and capabilities.
Map current capabilities and identify gaps using data-driven maturity models and assessments.
Integrate AI-skilling strategies into job architecture, leadership development, succession planning, and career pathing.
Culture & Change Leadership:
Shape a cultural foundation that enables experimentation, AI-augmented decision-making, and cross-functional collaboration.
Coach senior leaders to model AI-aligned mindsets and behaviors, and to lead teams through ambiguity and innovation.
Lead enterprise change management efforts to accelerate adoption of AI tools, practices, and decision-making frameworks.
Measurement & Impact Tracking:
Define and report on key metrics for AI maturity, capability adoption, workforce transformation, and business impact.
Build and maintain executive-level visibility into roadmap progress and readiness indicators.
Continuously iterate roadmap and enablement plans based on insights, adoption trends, and enterprise priorities.

Qualifications:

10+ years of experience in organizational change, transformation, talent strategy, or enablement leadership—preferably in a healthcare or tech-forward environment.
Strong understanding of AI technologies, tools, and business applications; formal technical background not required, but literacy is essential.
Proven experience designing, leading, and scaling enterprise-wide enablement and change initiatives.
Exceptional influencing, facilitation, and coaching skills with C-level leaders and cross-functional stakeholders.
Experience embedding ethics, risk, and governance frameworks into innovation or change programs is a strong asset.
Strategic thinker with operational discipline—able to move from vision to execution with clarity and agility.

What Success Looks Like:

A clearly defined and executed AI Organizational Capability Roadmap is guiding workforce, culture, and technology evolution.
AI adoption is purposeful, pervasive, and values-aligned, with strong cultural readiness and low risk of misuse.
Leaders are confident using AI to augment judgment and enhance business outcomes.
The workforce is actively reskilling and evolving in response to changing roles and strategic imperatives.
People systems, leadership behaviors, and the operating model are future-fit for continuous AI evolution.

\n $247,000 - $275,000 a year At PointClickCare, base salary is one of the many components that make up our total rewards package. The CA base salary range for this position is $247,000 - $275,000 + bonus or commission + equity + benefits. Our salary ranges are determined by job and level. The range displayed on each job posting reflects the target for new hire salaries for the position across all CA locations. 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. \n

LI-Remote

LI-JP1

Corp G/SL1

PointClickCare Benefits & Perks:

Benefits starting from Day 1!

Retirement Plan Matching

Flexible Paid Time Off

Wellness Support Programs and Resources

Parental & Caregiver Leaves

Fertility & Adoption Support

Continuous Development Support Program

Employee Assistance Program

Allyship and Inclusion Communities

Employee Recognition … and more!

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 recruitment@pointclickcare.com should you require any accommodations.

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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.