Director, People Strategy and HR Portfolio (Project) Management

Job Title: Director, People Strategy and HR Portfolio (Project) Management
Location: Mississauga, ON - Hybrid

**Travel to Office expectations**

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.

About the Team

The People Strategy & Transformation (PST) is PointClickCare's HR strategy, organizational design, and portfolio management pillar. The team includes HR Business Partners, Organizational Design & Effectiveness, People Experience, and the HR Strategy & Enablement function, with a dotted-line partnership to Internal Communications. PST is responsible for ensuring HR's work across every Center of Excellence is planned, resourced, sequenced, and tracked against business outcomes — spanning a portfolio of Pillar Initiatives, Cross-Pillar Projects, and Program Roll-Ups delivered across all four HR solution groups.

Position Summary:

The Director, People Strategy and HR Portfolio (Project) Managements is the VP, People Strategy & Transformation's strategic thought partner in building and running PointClickCare's HR Portfolio Management Office (HR PMO) — co-designing the strategy, governance model, capacity methodology, and dashboard reporting that let HR plan, resource, and track its work against business outcomes. This is a net-new function: no HR PMO currently exists at PointClickCare, and this role will design these mechanics in partnership with the VP rather than operate a system someone else has already built.

Operating with significant design authority but without direct reports or final decision rights on cross-functional trade-offs, this role earns influence through the credibility of the mechanics it builds and runs. It operates across all four HR solution groups without formal authority over any of them, serves as the VP's thought partner on HR strategy and the HR SLT prioritization process, and convenes HR initiative stakeholders and Internal Communications to coordinate how HR's work reaches the business.

Key Responsibilities:

Design and run the HR Portfolio Management Office’s core operating mechanics

• Design and maintain the capacity management methodology, including the heat map model and the oversubscription thresholds used to flag resourcing conflicts across HR COEs
• Own and run the Portfolio Council governance cadence end to end — intake, capacity check, tier assignment, publish, mid-quarter check, and close-out
• Build and maintain the integrated HR initiative dashboard, ensuring data currency and accuracy across every active Pillar Initiative, Cross-Pillar Project, and Program Roll-Up
• Example deliverable: a quarterly Portfolio Council capacity heat map showing every HR COE’s current initiative load, used to approve or defer new initiative intake

Serve as strategic thought partner to the VP, People Strategy & Transformation

• Co-design the HR SLT prioritization process and criteria used to evaluate and sequence HR initiatives each planning cycle
• Co-design the OKR and scorecard measurement architecture — what gets measured, how it rolls up, and the cadence it runs on
• Co-author and stress-test the HR Strategy on a Page, contributing independent analysis before it is finalized by the VP
• Example deliverable: a documented HR SLT prioritization framework — criteria, weighting, and process — adopted for the FY28 planning cycle

Own capacity management and project plan oversight across the full HR initiative portfolio

• Track progress against committed business outcomes, not activity completion alone, across every active HR initiative
• Maintain consistent project plan structure, milestone tracking, and dependency mapping in partnership with each initiative’s named Delivery Lead
• Proactively surface cross-COE capacity collisions and resourcing conflicts before they reach Portfolio Council
• Example deliverable: a consolidated project plan view across all active Program Roll-Ups, flagging dependency risk before it affects a committed milestone

Convene HR initiative stakeholders and Internal Communications on a recurring cadence

• Establish and run a recurring go-to-market coordination cadence bringing together initiative Delivery Leads and Internal Communications
• Sequence the timing and stakeholder readiness of HR initiative rollouts to the business, avoiding duplicate or conflicting messages landing in the same window
• Maintain a shared go-to-market calendar visible to HR SLT, showing what is launching, when, and to whom
• Example deliverable: a quarterly HR go-to-market calendar sequencing every planned initiative rollout to the business, reviewed and approved by HR SLT before the quarter begins

Represent HR in enterprise planning and governance forums

• Serve as the primary operational liaison to the Strategic Delivery Office, aligning HR’s initiative classification and intake practices to enterprise taxonomy
• Represent HR’s initiative portfolio and capacity picture in the Corporate Strategy Group’s quarterly planning cadence
• Flag enterprise-level dependencies or conflicts affecting HR’s ability to deliver against committed priorities
• Example deliverable: HR’s consolidated initiative and capacity submission into the Corporate Strategy Group’s quarterly planning sprint, reflecting current Portfolio Council status

Required Skills & Qualifications:

• 10–15 years of experience in program/portfolio management, management consulting, or a PMO leadership capacity, including demonstrated experience designing — not only operating — portfolio governance, capacity management, or OKR measurement systems
• A track record serving as a strategic thought partner to a senior leader, with evidence of shaping that leader's thinking rather than only executing direction
• Demonstrated experience operating in matrixed, cross-functional environments without formal authority over the teams being coordinated
• Strong data and dashboard fluency — comfortable architecting reporting tools and the metrics model behind them, not just maintaining an existing build
• Executive-level communication skills — this role prepares materials for and interacts directly with VP-level stakeholders across every HR pillar
• Experience convening cross-functional stakeholder groups to coordinate sequencing and alignment on complex, multi-team initiatives

Preferred Experience:

• Experience building a PMO or governance function from scratch, in a design capacity, rather than operating within an already-mature one
• HR domain experience, including familiarity with COE structures and business-outcome-linked workforce initiatives
• Experience partnering with internal communications or marketing functions on coordinated, multi-stakeholder rollouts

At PointClickCare, base salary is one of the many components that make up our total rewards package. The Canada base salary range for this position is $127,000 - $158,700 + bonus + 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 Canada 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.

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.

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: [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.

#LI-Hybrid