Sr. Director, HR Technology and AI Enablement

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:

The Sr. Director, HR Technology and AI Enablement, delivers PointClickCare's HR technology roadmap and leads the shift to an AI-first, agent-enabled model of HR service delivery. Reporting to the VP Total Rewards, the role executes the platform and AI strategy the pillar sets, redesigns HR workflows and AI-human handoffs ahead of the SAP SuccessFactors-to-Workday migration, and operationalizes the data governance and responsible-AI controls that make automation safe in a healthcare context. Partnering closely with the Sr. Director, HR COEs, SDO, Procurement and OCIO, the role leads a team through significant platform and ways-of-working change, turning pillar strategy into a working technology capability for PCC.

Key Responsibilities:

HR Technology Roadmap Execution & Platform Sequencing

• Co-develop with the Workforce Intelligence and HR Technology Leader and execute the multi-year HR technology roadmap Evaluate, select, and sequence platforms and agentic AI across the ecosystem (Workday, Moveworks, ServiceNow Now Assist, Payfactors, Power BI, Qualtrics) against business outcomes
Operating-Model & Workflow Redesign (ahead of Workday configuration)
• Partner with the HR COEs and the four-zone workflow classification to redesign HR workflows and AI–human handoffs before Workday is configured, so Zone 1 and Zone 2 automation is built natively pre-go-live rather than retrofitted. This sequencing is the highest-leverage lever for FY27 and prevents PCC from hardcoding today’s inefficiency into the system for years.
Platform Migration, AI Agent & Automation Delivery (SuccessFactors → Workday)
• Lead end-to-end delivery of the Workday migration and the deployment of conversational and agentic AI (Moveworks, Now Assist), owning project plans, configuration, testing, cutover, and hypercare. Define which workflows are automated versus human-led, monitor agent performance and quality, and manage vendors and budget. Close partnership & collaboration with Procurement, OCIO & SDO through all phases required. Final budget and contract decisions made with partners and Sr. Director
Data Governance, Privacy & Responsible AI
• Build and safeguard the data foundation for AI.": an HR data quality audit ahead of migration, operationalizing the data governance policy that defines what AI systems can access, and Workday as the single source of truth. Advance People Analytics maturity and the skills taxonomy that underpins workforce planning.
Team Leadership, Adoption & Employee Experience
• Lead and develop the HR technology team, reskilling it as work shifts from configuration to AI orchestration. Apply product and user-experience thinking, and drive adoption and change management so employees and managers experience HR technology as fast, intuitive, and trusted.

Required Skills & Qualifications:

• Bachelor’s degree in Human Resources, Information Systems, Computer Science, Business, or a related field.
• 10+ years of progressive HR technology / HRIS experience, including 5+ years leading and developing teams, and prior experience operating at a leader level or equivalent scope.
• Demonstrated experience leading an enterprise HCM platform implementation or migration (e.g., Workday and/or SAP SuccessFactors).
• Experience redesigning HR processes and workflows for automation — mapping current state, eliminating waste, and designing AI–human handoffs ahead of system configuration.
• Hands-on experience deploying or operating enterprise AI and automation tools — conversational and agentic AI and AI-enabled service management (e.g., ServiceNow / Now Assist, Moveworks).
• Strong AI literacy: a working understanding of large language models, AI agents, prompt design, and responsible/ethical AI, data governance, privacy, and security.
• People analytics and data fluency — able to turn HR data into insight and design trusted reporting and dashboards.
• Proven project and change management skills, delivering across cross-functional stakeholders and external vendors on time and on budget.
• Demonstrated experience owning technology vendor relationships and negotiating contracts at a half million threshold or above
• Product- and outcome-oriented mindset — frames technology investments in terms of business and employee-experience outcomes.

Preferred Experience:

• Workday certification(s) and/or ServiceNow HR Service Delivery experience.
• Experience in a high-growth SaaS or technology company.
• Experience establishing AI governance, human-in-the-loop frameworks, or classifying workflows by AI impact.
• Experience with integration architecture (APIs, iPaaS) and enterprise HR data governance.
• Experience with data privacy and security in a regulated or healthcare environment (e.g., PHI / HIPAA).
• Experience leading and developing a technical HR / HRIS team.
• Familiarity with UX and service-design methods applied to employee-facing technology.
• Relevant certifications (PMP, Prosci / change management, HRIP, CHRP / SHRM).

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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 [email protected] 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: [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.