Sr. Director, HR Technology and AI Enablement

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.

• 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.

• 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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