Sr. Director, HR Technology and AI Enablement

About the role

The Sr. Director, HR Technology and AI Enablement will shape PointClickCare’s HR technology roadmap and drive an AI‑first service model. Reporting to the VP Total Rewards, this leader will redesign workflows, oversee the SAP SuccessFactors‑to‑Workday migration and embed responsible AI controls across the HR ecosystem.

Key responsibilities

• Co‑develop and execute the multi‑year HR technology roadmap, selecting and sequencing platforms such as Workday, Moveworks, ServiceNow, Payfactors, Power BI and Qualtrics.
• Redesign HR workflows and AI‑human handoffs ahead of the Workday configuration to embed automation from day one.
• Lead the end‑to‑end migration from SAP SuccessFactors to Workday, including project planning, configuration, testing, cut‑over and hyper‑care, while deploying conversational and agentic AI solutions.
• Establish data‑governance, privacy and responsible‑AI controls, conduct HR data quality audits and define AI access policies.
• Build and develop the HR technology team, drive adoption, change management and a user‑centric experience.

Required profile

• Bachelor’s degree in Human Resources, Information Systems, Computer Science, Business or related field.
• 10+ years of progressive HR technology/HRIS experience, including 5+ years of leadership.
• Proven experience delivering an enterprise HCM platform implementation or migration (Workday and/or SAP SuccessFactors).
• Demonstrated ability to redesign HR processes for automation and to manage AI‑enabled service tools.

Required skills

• Workday
• SAP SuccessFactors
• ServiceNow / Now Assist
• Moveworks
• Power BI
• Qualtrics
• Large language models, AI agents and prompt design
• Data governance, privacy and security
• People analytics and data visualization