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Sr. Director, HR Technology and AI Enablement

PointClickCare· Human Resources
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Hybrid (Mississauga, Ontario)CA$163k - CA$181k + bonusFull-timePosted 1mo ago

About the role

Senior leadership role delivering the HR technology roadmap, leading AI-enabled HR service delivery, and overseeing the Workday migration, data governance, and HR technology transformation within PointClickCare.

Responsibilities

  • Co-develop and execute the multi-year HR technology roadmap with the Workforce Intelligence and HR Technology Leader; evaluate, select, and sequence platforms and AI across the ecosystem (Workday, Moveworks, ServiceNow Now Assist, Payfactors, Power BI, Qualtrics) against business outcomes
  • Redesign HR workflows and AI–human handoffs ahead of Workday configuration; implement Zone 1 and Zone 2 automation pre-go-live
  • Lead end-to-end delivery of the Workday migration and deployment of conversational and agentic AI (Moveworks, Now Assist); manage project plans, configuration, testing, cutover, and hypercare; define automated vs human-led workflows; monitor agent performance and vendor/budget management
  • Build and safeguard the data foundation for AI; conduct HR data quality audits ahead of migration; operationalize data governance policy; establish Workday as single source of truth; advance People Analytics maturity and skills taxonomy
  • Lead and develop the HR technology team; drive adoption and change management; apply product and UX thinking to ensure fast, intuitive, trusted HR technology

Qualifications

  • Bachelor’s degree in Human Resources, Information Systems, Computer Science, Business, or related field
  • 10+ years of progressive HR technology / HRIS experience; 5+ years leading and developing teams; leadership at senior level or equivalent scope
  • Experience leading enterprise HCM platform implementation or migration (e.g., Workday and/or SAP SuccessFactors)
  • Experience redesigning HR processes/workflows for automation; mapping current state; designing AI–human handoffs before system configuration
  • Hands-on experience deploying enterprise AI and automation tools (conversational and agentic AI; AI-enabled service management such as ServiceNow / Now Assist, Moveworks)
  • Strong AI literacy; understanding of LLMs, AI agents, prompt design, responsible/ethical AI, data governance, privacy, security
  • People analytics and data fluency; ability to turn HR data into insights and trusted dashboards
  • Proven project and change management skills; cross-functional stakeholder and vendor management; delivering on time and within budget
  • Experience owning technology vendor relationships and negotiating contracts at or above a half-million threshold
  • Product- and outcome-oriented mindset for technology investments

Skills

Required:HR Technology LeadershipWorkdayAI & Automation ToolsData Governance & PrivacyPeople Analytics
Nice to have:SAP SuccessFactors

Benefits

  • 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!
Last updated Oct 21, 2026. Interested? Apply on the company site.

About PointClickCare

Healthcare Software for Smarter Care Delivery | PointClickCare

Transform care coordination and outcomes with AI-powered healthcare software that improves collaboration, reimbursement, and transitions of care.

healthcare softwareEHRcare coordinationhealthcare solutionssenior livingskilled nursinghospitals & health systemscare outcomes
Company profileWebsite

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