Hybrid opportunity at
PointClickCareSr. Director, HR Technology and AI Enablement
This senior director role owns the company's HR technology roadmap and guides the push to deliver HR services through AI and autonomous agents. The director reports…
Career Tools
About This Role
This senior director role owns the company's HR technology roadmap and guides the push to deliver HR services through AI and autonomous agents. The director reports to the VP Total Rewards, carries out the platform and AI strategy set by that leader, and works with the Sr. Director of HR Centers of Excellence, the SDO, Procurement and the Office of the CIO. Before the Workday configuration starts, the director redesigns…
Job Description
This senior director role owns the company's HR technology roadmap and guides the push to deliver HR services through AI and autonomous agents. The director reports to the VP Total Rewards, carries out the platform and AI strategy set by that leader, and works with the Sr. Director of HR Centers of Excellence, the SDO, Procurement and the Office of the CIO.
Before the Workday configuration starts, the director redesigns HR workflows and the points where AI hands work to people. The posting treats this sequencing as the largest lever for the coming fiscal year, since it keeps automation from being bolted on later. The director also runs the move from SAP SuccessFactors to Workday and the rollout of conversational and agentic AI, including Moveworks and ServiceNow Now Assist, covering plans, testing, cutover and hypercare.
Further duties include deciding which workflows run automatically and which stay with people, managing vendors and budgets, and building a dependable data foundation for AI. The director leads and develops the HR technology team, drives adoption and change management, and aims to make HR tools feel fast and trustworthy to employees and managers.
The employer is a privately held health technology company that serves more than 30,000 provider organizations. The role is full time and hybrid. The listing does not give a city or a salary.
Responsibilities
- Build a multi-year HR technology roadmap in step with the Workforce Intelligence lead
- Weigh platforms and agent-based AI options against what the business needs, then set their order
- Rework HR processes and AI-to-people handoffs before Workday is configured
- Own delivery from start to finish for the move off SuccessFactors onto Workday and for launching AI agents
- Decide which workflows are automated and which stay with people, and monitor agent quality
- Manage technology vendors, contracts and budget, including final decisions with partners
- Audit HR data quality ahead of migration and make Workday the authoritative source
- Raise people analytics maturity and build the skills taxonomy used in workforce planning
- Lead and grow the HR technology team as its work shifts toward AI orchestration
- Lead adoption and change work so staff and managers come to trust the tools
Requirements
- Bachelor's-level education in HR, information systems, computer science or business, or in a closely related area
- Ten or more years of progressive HR technology or HRIS experience, including five or more years leading teams
- Background leading a large HCM platform rollout or move, for example to Workday or SAP SuccessFactors
- Experience reworking HR processes for automation and designing AI-to-people handoffs
- Hands-on work deploying or running enterprise AI and automation products
- Practical grasp of LLMs, agent-based AI, prompt design, and responsible AI, plus governance, privacy and security
- Skill at converting people data into findings and building reports and dashboards people can rely on
- Proven record managing projects and change across stakeholders and external vendors
- Experience owning vendor relationships and negotiating contracts of half a million or more
- Outcome-focused thinking that judges technology spend by business and employee-experience results
Qualifications
- Certification in Workday, or hands-on time with ServiceNow HR Service Delivery
- Time spent at a fast-growing SaaS or tech firm
- Track record setting up AI oversight, plus frameworks that keep people in the loop, and sorting workflows by AI impact
- Experience with integration architecture, including APIs and iPaaS, and with enterprise HR data governance
- Work on data privacy and security within a regulated or health-care environment, such as PHI and HIPAA
- Experience leading a technical HR or HRIS team
- Comfort with UX and service-design approaches for tools that employees use
- Certifications such as PMP, Prosci, HRIP or CHRP and SHRM
Core Skills
Benefits
- Benefits begin on the first day of employment
- Retirement plan with employer matching
- Flexible paid time off
- Wellness resources and support programs
- Parental and caregiver leave
- Fertility and adoption assistance
- Learning and development support
- Employee assistance program
- Inclusion and allyship groups
- Employee recognition
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Which executive does this director role answer to?
The role reports to the VP Total Rewards, according to the posting.
What experience is required?
The posting asks for a bachelor's degree, ten or more years in HR technology or HRIS, five or more of them leading teams, and past work leading a large HCM platform change.
Which platforms are named?
The posting lists several platforms in scope, among them Workday, SAP SuccessFactors, Moveworks and Power BI.
Does the posting state a salary or location?
No. It does not give a salary or a specific office city, and it describes the role as hybrid.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.
