Posted 29 days ago

Sr. Director, HR Technology and AI Enablement

MississaugaHybridFull-time

AI Summary

Leads PointClickCare's HR technology roadmap and AI enablement, driving the shift to an AI-first, agent-enabled HR service model and overseeing the SAP SuccessFactors-to-Workday migration.

About 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).

Skills

AI AgentsChange ManagementData GovernanceData PrivacyHIPAAMoveworksPayfactorsPeople AnalyticsPower BIProject ManagementPrompt DesignQualtricsResponsible AISAP SuccessFactorsServiceNow Now AssistUX DesignVendor ManagementWorkday