Leads PointClickCare’s HR technology roadmap, Workday migration, AI-agent deployment, workflow redesign, data governance, and responsible AI controls. Oversees HR technology teams, vendors, budgets, configuration, testing, cutover, hypercare, adoption, and change management. Partners cross-functionally to improve HR service delivery, establish trusted data and reporting, and redesign processes for safe automation and effective AI-human collaboration.
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:
- 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
- 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.
- 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
- 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.
- 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.
HR Technology Roadmap Execution & Platform Sequencing
Operating-Model & Workflow Redesign (ahead of Workday configuration)
Platform Migration, AI Agent & Automation Delivery (SuccessFactors → Workday)
Data Governance, Privacy & Responsible AI
Team Leadership, Adoption & Employee Experience
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).
PointClickCare Toronto, Ontario, CAN Office
Toronto, Canada
PointClickCare Mississauga, Ontario, CAN Office
5570 Explorer Drive, Mississauga, Ontario, Canada
PointClickCare Waterloo, Ontario, CAN Office
611 Kumpf Drive, Waterloo, Canada, N2V 1K8
Similar Jobs
eCommerce • Fashion • Retail • Sales • Wearables • Design
Provides personalized styling advice, product recommendations, and customer service in a Kate Spade retail store. Responsibilities include driving sales through customer engagement and storytelling, completing POS transactions, maintaining stockroom organization, supporting virtual selling, and collaborating with the team. The role requires flexible scheduling, retail experience, strong communication skills, and the ability to perform physical tasks such as lifting, bending, and maneuvering through sales and stockroom areas.
Top Skills:
Pos
Artificial Intelligence • Big Data • Enterprise Web • Fintech • Software • Financial Services
Lead analyst responsible for managing a portfolio of Canadian banks, non-bank financial institutions, and credit unions. Perform ongoing financial and credit analysis, prepare rating committee presentations, reports and press releases, attend issuer meetings, participate in rating committees, and maintain client relationships. Produce surveillance, research, and written analysis while collaborating with the ratings team.
Top Skills:
Bloomberg
Cloud • Information Technology • Internet of Things • Machine Learning • Software • Cybersecurity • Infrastructure as a Service (IaaS)
Leads functional systemization and solution design for radio and wireless communication products. Translates customer, market, regulatory, and product requirements into system requirements, interfaces, behaviors, and acceptance criteria. Leads feasibility studies, architecture evaluations, and technical investigations; provides recommendations, root-cause analysis, and technical leadership across hardware, software, security, verification, and product management teams. Supports secure-by-design development, compliance, planning, prioritization, mentoring, and global stakeholder alignment.
Top Skills:
CybersecurityRadio Access Networks (Ran)TelecommunicationsWireless Communication Systems
What you need to know about the Toronto Tech Scene
Although home to some of the biggest names in tech, including Google, Microsoft and Amazon, Toronto has established itself as one of the largest startup ecosystems in the world. And with over 2,000 startups — more than 30 percent of the country's total startups — Toronto continues to attract new businesses. Be it helping entrepreneurs manage their finances, simplifying business operations by automating payroll or assisting pharmaceutical companies in launching new drugs, the city's tech scene is just getting started.
