# Senior Director, HR Technology and AI Enablement

**Company:** [PointClickCare](https://hotfix.jobs/companies/pointclickcare)
**Location:** Mississauga, Canada
**Role:** Engineering Management
**Salary:** CA$163k – CA$181k/yr
**Experience:** 10+ years
**Skills:** Workday, Sap Successfactors, Moveworks, Servicenow Now Assist, HRIS, AI Agents, LLMs, Prompt Design, Data Governance, People Analytics, Power BI, APIs, Ipaas, HIPAA
**Posted:** 2026-08-26

> Leads HR technology strategy execution, Workday migration, AI-enabled HR service delivery, workflow redesign, and responsible data governance. The role requires 10+ years of HR technology experience, enterprise HCM migration expertise, strong AI literacy, and substantial team leadership experience.

## Job Description

## Responsibilities
- Execute the multi-year HR technology roadmap and sequence platforms and agentic AI against business outcomes.
- Redesign HR workflows and AI–human handoffs before Workday configuration, eliminating waste and enabling appropriate automation.
- Lead the end-to-end migration from SAP SuccessFactors to Workday, including planning, configuration, testing, cutover, and hypercare.
- Deploy and operate conversational and agentic AI tools, including Moveworks and ServiceNow Now Assist.
- Define automated versus human-led workflows, monitor agent performance and quality, and manage vendors, contracts, budgets, and cross-functional delivery.
- Establish HR data quality, governance, privacy, security, and responsible-AI controls, with Workday as the source of truth.
- Advance people analytics, workforce-planning data, and skills-taxonomy capabilities.
- Lead and develop the HR technology team, reskill it for AI orchestration, and drive adoption and change management.

## Requirements
- Bachelor’s degree in Human Resources, Information Systems, Computer Science, Business, or a related field.
- 10+ years of progressive HR technology or HRIS experience, including 5+ years leading and developing teams.
- Experience operating at a leader level or equivalent scope.
- Enterprise HCM implementation or migration experience, such as Workday or SAP SuccessFactors.
- Experience redesigning HR processes and workflows for automation and AI–human handoffs.
- Hands-on experience with enterprise conversational or agentic AI and AI-enabled service management.
- Working knowledge of large language models, AI agents, prompt design, responsible AI, data governance, privacy, and security.
- People analytics and data fluency, including trusted reporting and dashboards.
- Project and change management experience delivering cross-functional, vendor-supported initiatives on time and on budget.
- Experience managing technology vendors and negotiating contracts at a half-million-dollar threshold or above.
- Product- and outcome-oriented approach to technology and employee experience.

## Nice-to-haves
- Workday certifications 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 AI-impact workflow classifications.
- Integration architecture experience, including APIs and iPaaS.
- HR data governance and privacy/security experience in regulated or healthcare environments, including PHI or HIPAA.
- Experience leading technical HR or HRIS teams.
- UX and service-design experience for employee-facing technology.
- PMP, Prosci, HRIP, CHRP, or SHRM certification.

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