---
title: 'Sr. Director, HR Technology and AI Enablement at PointClickCare'
canonical: 'https://feeny.ai/job/sr-director-hr-technology-and-ai-enablement-pointclickcare-mississauga-gmtxzaew8eyz'
type: 'job'
last_seen: '2026-09-14'
---

# Sr. Director, HR Technology and AI Enablement at PointClickCare

- **Company:** PointClickCare
- **Location:** Mississauga, Canada
- **Compensation:** $163k–$181k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-08-26
- **Last confirmed live:** 2026-09-14
- **Apply:** https://jobs.lever.co/pointclickcare/f949e9b0-23dc-4f31-8e46-79eeb79bb79b

## 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).

## #LI-TW1

#LI-Hyrbid

## About PointClickCare

## Company Overview
- **One-liner**: PointClickCare provides a cloud-based electronic health record (EHR) and care collaboration platform for senior living, skilled nursing, and post-acute care providers, serving as North America’s #1 senior care EHR.
- **Entity Type**: Private (Late Stage)
- **Headquarters**: Mississauga, Ontario, Canada
- **Founded**: 2000
- **Founders**: Mike Wessinger and Dave Wessinger

## Core Business
- **Primary industry**: Healthcare IT – specifically electronic health records (EHR), care coordination, and value-based care solutions for long-term and post-acute care (LTPAC) and senior living.
- **Target customers**: B2B – skilled nursing facilities, assisted living communities, continuing care retirement communities, acute care hospitals, health plans, and other post-acute providers.
- **Mission / Purpose**: To make healthcare more connected, efficient, and insight-driven by transforming how care is planned, delivered, and paid for – ultimately improving outcomes for millions of patients.

## Products & Services
- **PointClickCare EHR**: Industry-leading, integrated electronic health record for senior living and long-term care, with purpose-built workflows for move-in, service delivery, billing, and clinical documentation.
- **AI-Informed Healthcare**: Proprietary AI model trained on the largest LTPAC dataset in North America to identify high-risk patients, reduce readmissions, and streamline care coordination using predictive, chart-level insights.
- **Intelligent Transitions**: Tools that use billions of patient data points to provide care teams with proactive, actionable insights for optimizing patient transitions across acute and post-acute settings.
- **Reimbursable Outcomes**: Advanced analytics that connect clinical outcomes to reimbursement, helping providers and payers improve quality scores, meet value-based care goals, and navigate financial complexities.
- **PointClickCare Marketplace**: An ecosystem of 400+ integrated third-party partners that allows organizations to customize and extend their care platform.

*Each product is a SaaS offering, delivered as part of a unified cloud platform.*

## Market Standing
- **Valuation**: $4 billion as of the latest reported round ([Tracxn](https://tracxn.com/d/companies/pointclickcare/__HQJYcaarZQgBhkk16un5Vwr98WSt4aEIr6x0wRz22YY))
- **Total Funding**: $283 million raised across 5 rounds; notable investors include **Dragoneer Investment Group** and **Hellman & Friedman** ([Tracxn](https://tracxn.com/d/companies/pointclickcare/__HQJYcaarZQgBhkk16un5Vwr98WSt4aEIr6x0wRz22YY))
- **Key Metric**: Trusted by more than **30,000 provider organizations**; serves every major US health plan; network accounts for **700M+ total patient visits**; **#1 senior care EHR in North America** ([PointClickCare](https://pointclickcare.com/company/about-us/))
- **Growth Signals**:
  - Acquired three companies in recent years: **American HealthTech** (2024), **Patient Pattern** (2023), and **Audacious Inquiry** (2022) to expand capabilities in AI, health data exchange, and revenue cycle management ([Tracxn](https://tracxn.com/d/companies/pointclickcare/__HQJYcaarZQgBhkk16un5Vwr98WSt4aEIr6x0wRz22YY))
  - Recognized as a **Forbes top 100 private cloud company** ([PointClickCare](https://pointclickcare.com/company/about-us/))
  - Employee count of **1,500** as of March 2025 ([Tracxn](https://tracxn.com/d/companies/pointclickcare/__HQJYcaarZQgBhkk16un5Vwr98WSt4aEIr6x0wRz22YY))
- **Annual Revenue**: Not publicly available (private company).

## Competitive Advantages
- **Largest LTPAC dataset in North America** – Powers a proprietary AI model that delivers predictive, chart-level insights unmatched by competitors.
- **Network effects** – A vast, integrated ecosystem of 400+ partners and connections to every major US health plan creates high switching costs and deep data interoperability.
- **20+ years of founder-led innovation** (independent since 2000), with deep domain expertise in senior care and post-acute value-based care.
- **#1 senior care EHR** brand recognition and trust among 30,000+ provider organizations.

## Strategic Focus
- **Value-based care enablement**: Helping providers and payers improve outcomes while navigating value-based reimbursement models through analytics and intelligent transitions.
- **AI-first innovation**: Expanding the use of proprietary AI to reduce clinician administrative burden, identify high-risk patients, and optimize care coordination.
- **Platform expansion**: Growing the marketplace and integration ecosystem to become the operating system for the entire LTPAC continuum.
- **Continued M&A**: Pursuing strategic acquisitions to broaden functionality (clinical AI, revenue cycle, health data exchange) and geographic footprint.

## Why Work Here
- **Culture & Inclusion**: Emphasizes a culture of belonging through an **Allyship & Inclusion Community** and values diverse backgrounds and perspectives ([Life at PointClickCare](https://pointclickcare.com/life-at-pointclickcare/))
- **Work Flexibility**: Offers **flex work and time off** with a hybrid model to support work-life balance ([Life at PointClickCare](https://pointclickcare.com/life-at-pointclickcare/))
- **Learning & Growth**: Provides continuous learning opportunities and career development resources, including internship and co-op programs for students ([Life at PointClickCare](https://pointclickcare.com/life-at-pointclickcare/))
- **Competitive Benefits**: Competitive compensation, incentives, recognition programs, and rewards ([Life at PointClickCare](https://pointclickcare.com/life-at-pointclickcare/))
- **Impactful Mission**: Work on technology that directly improves the quality of care for millions of seniors and patients across North America.
- **Headcount**: 1,500 employees as of March 2025, indicating a scaling organization with room for career growth.

## Sources
1. [PointClickCare About Us](https://pointclickcare.com/company/about-us/)
2. [Life at PointClickCare](https://pointclickcare.com/life-at-pointclickcare/)
3. [PointClickCare Careers on Lever](https://jobs.lever.co/pointclickcare)
4. [Tracxn Company Profile](https://tracxn.com/d/companies/pointclickcare/__HQJYcaarZQgBhkk16un5Vwr98WSt4aEIr6x0wRz22YY)
5. [PointClickCare Main Site](https://pointclickcare.com/)

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