Director, ITS, FASTech

2 weeks ago

Mississauga, Ontario, Canada Chartwell Retirement Residences Full time $90,000 - $120,000 per year

The Opportunity

The Director, ITS, FASTech & Innovation leads a rapid-delivery team within Chartwell's IT Services division. The role drives small, high-impact technology projects that apply automation, AI, and innovation to improve efficiency and employee experience.

Working in four- to eight-week Agile cycles, the Director partners with business leaders to identify opportunities, deliver solutions across Chartwell's technology ecosystem (Microsoft 365, Power Platform, UiPath, Copilot, ChatGPT, Yardi, Oracle HCM Cloud, ServiceNow), and ensure measurable business outcomes.

This position combines strategic leadership with hands-on technical delivery, balancing innovation with governance and compliance.

Key Accountabilities

Strategic Leadership

  • Identify and prioritize automation and AI opportunities with business leaders.
  • Build a pipeline of rapid-delivery projects aligned with enterprise priorities.
  • Promote agility, collaboration, and continuous improvement.

Project Delivery

  • Lead 4–8 week Agile projects from design to deployment.
  • Configure and implement AI workflows and automation solutions.
  • Manage scope, resources, risks, and timelines.

Technology Enablement

  • Leverage Microsoft 365, UiPath, Copilot, ChatGPT, Yardi, Oracle HCM Cloud, and ServiceNow.
  • Pilot and integrate emerging AI technologies.
  • Ensure compliance with security and IT standards.

Team Leadership

  • Lead and mentor analysts, project managers, and specialists.
  • Foster accountability, growth, and innovation.
  • Manage external consultants as needed.

Governance & Compliance

  • Uphold IT governance, change management, and security policies.
  • Maintain documentation and report on outcomes and ROI.

Qualifications

Education

  • Degree in Computer Science, Business Administration, or related field.
  • Agile/PMP and ITIL certifications are assets.

Experience

  • 7+ years in IT or Business Systems Analysis with leadership in automation, AI, or digital transformation.
  • Hands-on experience with AI tools (Copilot, ChatGPT, UiPath).
  • Strong background in Power Platform, ServiceNow, and RPA.
  • Experience managing hybrid teams and vendors.
  • Sector experience in seniors housing, real estate, or healthcare is an asset.

Skills & Abilities

  • Strong technical aptitude in AI and automation.
  • Knowledge of prompt engineering and generative AI.
  • Excellent analytical, design, and project management skills.
  • Strategic thinker, proactive, adaptable, and collaborative.
  • Bilingualism (English / Functional French) is an asset.

Effort

  • High mental effort to analyze, prioritize, and manage competing demands.
  • Physical effort limited to computer work and meetings.

Working Conditions

  • Office-based with hybrid flexibility.
  • Occasional non-standard hours during key deliverables.

Special Requirements

  • Criminal background check required.

At Chartwell, we're all about Making People's Lives BETTER: the lives of our residents and their families, and the lives of our employees. Join an exceptional group of diverse, inspiring, and caring people who are empowered to provide personalized, human experiences for our residents and staff through the connections they make every day within our communities.

Chartwell's commitment to diversity and inclusivity is a commitment to hiring people whose skills and abilities contribute the most to the success of the organization and who reflect the communities in which we live and work. We are an equal opportunity employer and welcome applications from a wide range of qualified candidates, including people with disabilities. If you have questions or require assistance with the application process, please email or call

We thank all applicants for their interest, however, only those selected for further consideration will be contacted.

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