(Canada) Principal Program Manager at PointClickCare

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. **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. Position Summary: Reporting to the Director, Portfolio Management, you will act as the primary client liaison to lead the implementation of projects and program workstreams within the Strategic Delivery Office of PointClickCare. You will support multi-year enterprise transformation programs and/or individual projects governed by the SDO, ensuring alignment with transformation strategy and portfolio-level objectives. This role will be responsible for managing both standalone projects and workstreams embedded within larger transformation programs, requiring strong collaboration with Program Directors, Business stakeholders, OCM partners, PO’s and Enterprise Architecture teams. Key Responsibilities: • Enterprise Project & Program Delivery Leadership • Own end-to-end delivery of complex projects and embedded workstreams within enterprise transformation programs: • Act as primary client liaison for SDO-governed projects and programs • Lead standalone projects and workstreams within multi-year, cross-functional transformation programs • Ensure alignment with transformation strategy, portfolio objectives, and program roadmaps • Maintain momentum, cohesion, and clear ownership across all workstreams • Manage day-to-day operational execution, including task definition and resource allocation • Participate in integrated planning rhythms across SDO programs • Governance, Planning & Financial Management • Apply PMO best practices to deliver projects on time, on budget, and in alignment with SDO governance standards: • Develop and maintain project plans using PMO methodologies tailored to stakeholder needs • Ensure adherence to SDO intake, prioritization, governance, and reporting standards • Manage project scope, budget, timelines, and resourcing • Assess and manage scope changes, including impact analysis on budget, schedule, and capacity • Drive benefits realization by ensuring scope and solutions align to intended business outcomes • Stakeholder, Executive & Vendor Management • Enable informed decision-making through strong stakeholder engagement, executive communication, and vendor oversight: • Communicate project status, milestones, budget tracking, and risks to executive sponsors and business stakeholders • Own escalation and change control processes, ensuring timely resolution • Prepare and maintain all project management reports using SDO-standard formats • Contribute to portfolio dashboards and integrated program reporting • Coordinate with vendors from SOW development through delivery • Manage vendor onboarding, accountability to contract, deliverables, and timelines • Lead vendor calls and maintains productive vendor relationships • Risk, Change & Data-Driven Decision Management • Proactively manage risk, change, and delivery insights to protect outcomes and enable adoption: • Identify, assess, and manage project risks and issues with appropriate urgency • Facilitate problem-solving by bringing the right stakeholders together and driving closure • Own accountability for decision-making at the appropriate organizational level • Integrate Organizational Change Management into project planning • Partner with Program Change Directors on readiness, impacts, communications, adoption, and collision risks • Leverage data-driven metrics and AI-enabled insights for forecasting, risk identification, and stakeholder communication • PMO Capability Building & Organizational Contribution • Strengthen enterprise delivery maturity through PMO capability development and continuous improvement: • Build deep understanding of business functions and technical needs • Foster growth of project management capabilities within the PMO • Share best practices, tools, and lessons learned across teams • Contribute to the overall goals and objectives of the Project Management Office • Support adoption of project metrics, dashboards, and AI-assisted delivery tools Required Skills & Experience: • Experience: • 5–10 years of professional project management experience in complex environments • Demonstrated experience leading agile projects or programs end‑to‑end, including scope, schedule, budget, and resources • Experience working in matrixed organizations with cross‑functional teams and shared accountability • Proven experience managing project risks, issues, dependencies, and escalations • Core Skills & Capabilities: • Strong project planning and execution using PMO best practices and governance standards • Ability to manage scope changes and clearly communicate impacts to budget, schedule, and resourcing • Excellent stakeholder and executive communication skills, including status reporting and escalation management • Strong analytical and problem‑solving skills, including basic root cause analysis • High attention to detail, organization, and time management • Proven experience delivering agile and waterfall projects and programs/initiatives • Tools & Ways of Working: • Proficiency with project management and productivity tools (e.g., MS Office, JIRA, Aha! or similar) • Experience gathering, analyzing, and reporting project metrics and dashboards • Comfort working in data‑driven environments and interpreting metrics to inform decisions • Experience working with AI‑assisted delivery, forecasting, or analytics tools • Strong business acumen with the confidence to drive accountability and decision ownership at senior levels Preferred Experience: • Experience managing projects in one or more of the following areas: • Enterprise-wide transformation programs • Technology modernization projects • Multi-vendor delivery projects • Cross-functional multi-team delivery initiatives • Experience delivering workstreams within enterprise‑wide, multi‑year transformation programs • Experience supporting digital transformation, enterprise information management, or Corporate Data Office initiatives • Experience partnering with Organizational Change Management (OCM) teams to manage readiness, adoption, and change impacts • Demonstrated ability to integrate change management activities into project delivery • PMP, Agile, or equivalent certification preferred #LI-TW1 #LI-Remote Tech - E Professional - 4 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 [Upgrade to PRO to see contact] should you require any accommodations. As part of our commitment to a streamlined and equitable hiring experience, PointClickCare uses AI tools to assist with candidate screening and assessment. When you apply for a position, your information is processed and stored with Lever, in accordance with Lever’s Privacy Policy. We use this information to evaluate your candidacy for the posted position. We also store this information, and may use it in relation to future positions to which you apply, or which we believe may be relevant to you given your background. When we have no ongoing legitimate business need to process your information, we will either delete or anonymize it.  If you have any questions about how PointClickCare uses or processes your information, or if you would like to ask to access, correct, or delete your information, please contact PointClickCare’s human resources team: [Upgrade to PRO to see contact]  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.