The Role
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.
Summary Generated by Built In
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).
Skills Required
- Bachelor’s degree in Human Resources, Information Systems, Computer Science, Business, or a related field
- 10+ years of progressive HR technology or HRIS experience
- 5+ years leading and developing teams, with prior leader-level experience or equivalent scope
- Experience leading an enterprise HCM platform implementation or migration, such as Workday or SAP SuccessFactors
- Experience redesigning HR processes and workflows for automation, including current-state mapping, waste elimination, and AI-human handoffs
- Hands-on experience deploying or operating enterprise conversational AI, agentic AI, or AI-enabled service management tools
- Working knowledge of large language models, AI agents, prompt design, responsible AI, data governance, privacy, and security
- People analytics and data fluency, including developing trusted reporting and dashboards
- Proven project and change management experience delivering cross-functional initiatives with vendors on time and within budget
- Experience owning technology vendor relationships and negotiating contracts at or above a $500,000 threshold
- Product- and outcome-oriented approach connecting technology investments to business and employee-experience outcomes
- Workday certification 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 AI-impact workflow classifications
- Experience with integration architecture, APIs, iPaaS, and enterprise HR data governance
- Experience with data privacy and security in a regulated or healthcare environment, including PHI or HIPAA
- Experience leading and developing a technical HR or HRIS team
- Familiarity with UX and service-design methods applied to employee-facing technology
- PMP, Prosci, HRIP, CHRP, SHRM, or other relevant certifications
PointClickCare Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about PointClickCare and has not been reviewed or approved by PointClickCare.
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Healthcare Strength — Health and dental coverage appear robust, with wellness and assistance programs reinforcing core medical benefits. Coverage quality stands out relative to other benefit elements.
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Leave & Time Off Breadth — PTO and paid holidays are characterized as generous, and flexible work-from-home options are widely available. Occasional extras like summer half‑day Fridays further expand time-off flexibility.
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Flexible Benefits — A customizable mix is evident through remote/hybrid arrangements, day-one eligibility, and a lifestyle or personal spending account. Benefits such as wellness credits and support resources can be tailored to individual needs.
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The Company
What We Do
PointClickCare is the market leader driving the transformation of healthcare vulnerable and complex populations through a broad, connected care network powered by deep insights with a commitment to value, outcomes and innovation. We connect post-acute and acute care settings, people and systems like no other company. Our steadfast commitment to our culture and to providing growth opportunities to our employees is evidenced by recent recognition of PointClickCare as one of Canada’s best-managed companies and most admired corporate cultures.
