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Manager, Data Engineering and Analytics
RBC
Toronto, ON
Full-time
Lead End-to-End Business & Systems Analysis for data engineering and AI-driven projects conduct requirements gathering, gap analysis, process mapping, and develop functional specifications…
Enterprise Architect - 6 Month Term
Moby
Calgary, AB
$75,000 to $100,000 CAD / year
Full-time
Lead the migration: Lead the consolidation onto a single modern platform, including the migration of billing, provisioning, and CRM off legacy systems - with correctness non-negotiable on…
Director, HR Tech (M&A and CNB)
Royal Bank of Canada
Toronto, ON
Full-time
Oversees the design, development, and modernization of platforms, managing cross functional teams and collaborating with senior leadership to drive transformational technology changes that…
Director, HR Tech (M&A and CNB)
RBC
Toronto, ON
Full-time
Oversees the design, development, and modernization of platforms, managing cross functional teams and collaborating with senior leadership to drive transformational technology changes that…
Senior Consultant, Procurement Transformation
KPMG
Calgary, AB · Vancouver, BC · ON · Toronto, Ontario
Full-time
Participate in the functional design and configuration of solutions such as SAP IBP, Blue Yonder, o9 Solutions, and Kinaxis.
Senior Consultant, Procurement Transformation
KPMG Canada
Toronto, ON
Full-time
Participate in the functional design and configuration of solutions such as SAP IBP, Blue Yonder, o9 Solutions, and Kinaxis.
Senior Consultant, Procurement Transformation
KPMG Canada
Vancouver, BC
Full-time
Participate in the functional design and configuration of solutions such as SAP IBP, Blue Yonder, o9 Solutions, and Kinaxis.
Senior Consultant, Procurement Transformation
KPMG Canada
Calgary, AB
Full-time
Participate in the functional design and configuration of solutions such as SAP IBP, Blue Yonder, o9 Solutions, and Kinaxis.
IT Manager
Safe Fleet
Montreal, Quebec
Full-time
Lead and develop a small, cross-functional IT team:
Forward Deployed Engineer
Synechron
Montreal, QC
Full-time
Serve as the technical lead within a small, cross-functional pod alongside business sponsors and process owners.
Supply Chain Manager
Colas Western Canada Inc.
St. Albert, AB
Full-time
This is a dynamic leadership role for someone who can balance long-term strategy with day-to-day execution. You may be reviewing supplier performance metrics and sourcing opportunities in…
Sr. Director, HR Technology and AI Enablement
PointClickCare
Mississauga, ON
$163,000 to $181,000 CAD / year
Full-time
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…
Sr. Director, HR Technology and AI Enablement
PointClickCare
Mississauga, ON
Full-time
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…
IT Business Analyst - Manufacturing Solutions
Bombardier
Montreal, Quebec · St-Laurent, Québ
Support the enterprise-wide deployment of SAP S/4HANA, including the transition from the legacy SAP ECC platform.
L4 Software Developer
TELUS Digital
Remote, Canada
$110,000 to $115,000 CAD / year
Full-time · Remote
TELUS Digital is seeking a Senior Technical Lead (L4) to join our NCCS engineering team. This role is ideal for a hands-on technical leader with strong experience in Java development,…
Team Lead, Cloud Business Office (CBO)
BRP
Montreal, QC · Greater Montreal Metropolitan Area
Full-time
The Cloud Business Office is seeking a security-focused Team Lead to operate, secure, and continuously improve our Azure and Google Cloud Platform (GCP) landscape through implementing…
Team Lead, Cloud Business Office (CBO)
BRP
Montreal, Quebec
Full-time
The Cloud Business Office is seeking a security-focused Team Lead to operate, secure, and continuously improve our Azure and Google Cloud Platform (GCP) landscape through implementing…
Principal Development Architect
SAP
Montreal, QC
We are looking for an experienced AI Development Architect to design, develop, and lead the implementation of innovative Industry AI solutions. The ideal candidate combines strong software…
Technical Lead Salesforce, Dealer Experience
BRP
Montreal, QC
Full-time
As the Salesforce Tech Lead, you will provide the squad’s technical leadership. Salesforce will be your primary area of expertise, while your role will also cover integrations, data flows…
Sr. Manager, Performance Systems
HOOPP (Healthcare of Ontario Pension Plan)
Toronto, ON · CA ON Toronto
Full-time
Lead analysis, integrations, and testing of new products / functionality as part of cross functional teams e.g. operational readiness for new investments / strategies, testing and…
Manager, Procurement Transformation
KPMG
Calgary, AB · Vancouver, BC · ON · Toronto, Ontario
Full-time
Lead or oversee the selection, design, and implementation of planning solutions such as SAP IBP, Blue Yonder, o9 Solutions, Kinaxis, or other comparable platforms.
Manager, Procurement Transformation
KPMG Canada
Toronto, ON
Full-time
Lead or oversee the selection, design, and implementation of planning solutions such as SAP IBP, Blue Yonder, o9 Solutions, Kinaxis, or other comparable platforms.
Manager, Procurement Transformation
KPMG Canada
Vancouver, BC
Full-time
Lead or oversee the selection, design, and implementation of planning solutions such as SAP IBP, Blue Yonder, o9 Solutions, Kinaxis, or other comparable platforms.
Manager, Procurement Transformation
KPMG Canada
Calgary, AB
Full-time
Lead or oversee the selection, design, and implementation of planning solutions such as SAP IBP, Blue Yonder, o9 Solutions, Kinaxis, or other comparable platforms.
Consultant, Application Development (SAP)
CIBC
Toronto, ON
Full-time
Relationship Management- Build strong relationships with functional teams, project stakeholders, and business partners to understand business needs and translate them into robust technical…

PointClickCare

Sr. Director, HR Technology and AI Enablement

Mississauga, ON, Canada

Pay: $163,000 to $181,000 CAD / year
Job type: Full-time
Apply by: Sep 25, 2026

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At a glance

Automatically prepared from the listing. Check the original description for the full requirements.

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Responsibilities

Lead the HR technology roadmap and the transition to an AI-first service delivery model, specifically managing the migration from SAP SuccessFactors to Workday. Responsible for redesigning HR workflows, implementing agentic AI tools, and establishing data governance and responsible AI controls.

Requirements

Requires a bachelor's degree and over 10 years of HR technology experience, including 5+ years of leadership and a proven track record of enterprise HCM migrations. Must possess strong AI literacy and experience deploying conversational AI tools like Moveworks or ServiceNow.

Experience

10+ years

Education

bachelor degree
professional certificate

Working hours

40 hours per week

Work arrangement

On-site

Skills

HR Technology Strategy
AI Orchestration
Workday Implementation
Workflow Redesign
Data Governance
People Analytics
Change Management
Vendor Management
Responsible AI
HCM Platform Migration
Project Management
User Experience Design

Benefits

Bonus
Equity
Benefits

Visa sponsorship

Not detected in the job text

Keywords

Workday
SAP SuccessFactors
Moveworks
ServiceNow Now Assist
Payfactors
Power BI
Qualtrics
Agentic AI
Large Language Models
Prompt Design
HCM
HRIS
Data Governance
HIPAA
PHI
PMP
Prosci
HRIP
CHRP
SHRM
iPaaS
APIs
SaaS
People Analytics
Human-in-the-loop
UX Design
Service Design

Original job description

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).

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.

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 $163,000 - $181,000 + 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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