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Sr. Director, HR Technology and AI Enablement
Job Location:
Job Location:
Mississauga - Canada
Yearly Salary:
$ 163000 - 181000
Yearly Salary:
Posted:
28 August 2026 (5 days ago)
Posted:
Application Deadline:
25 November 2026
Application Deadline:
Vacancies:
1 Vacancy
Vacancies:
Job Summary
Position Summary:
The Sr. Director HR Technology and AI Enablement delivers PointClickCares 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 AIhuman 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 todays 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:
- Bachelors 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 AIhuman 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).
$163000 - $181000 a year
At PointClickCare base salary is one of the many components that make up our total rewards package. The Canada base salary range for this position is $163000 - $181000 bonus equity benefits non-overtime eligible. Our salary ranges are determined by job and level. The range displayed on each job posting reflects the target for new hire salaries for the position across all Canada locations. Within the range individual compensation is determined by job-related skills and knowledge relevant experience including professional and lived experience and/or work location. Your recruiter can share more information about our total rewards package during the hiring process.
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We may use artificial intelligence (AI) tools to support parts of the hiring process such as reviewing applications analyzing resumes or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed please contact us.
Required Experience:
Exec
About Company
PointClickCare is the #1 cloud-based healthcare software provider helping long-term and post-acute care (LTPAC) providers navigate the new realities of value-based healthcare.
