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) Management s 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 ski