Job Specifications
Job available in these locations:
Toronto, Ontario, Canada
Windsor, Ontario, Canada
WHO WE ARE
When it comes to health, we’re always looking for ways to push for better. It’s why we were founded in the first place. In 1957, our founder, pharmacist William Wilkinson, witnessed a mother sacrifice her health by forgoing her own medicine to pay for her sick daughter’s prescription. He knew there had to be a better way. So, he introduced North America’s first prepaid drug plan, and GreenShield was born as a not-for-profit with a mission to support better health for all Canadians.We aren’t just a health and benefits company. We’re the only not-for-profit social enterprise that brings worlds of coverage and care together, all in one plac
e.We’re noble challengers, purposefully building a better way and we need the best people to help us create a more holistic approach that takes care of the mind and body.
Our mission is to create better health for all Canadians, and we know that starts with our employees.
THE ROLE IN A NUTSHELL
GreenShield is seeking a visionary leader to drive our digital workplace transformation. As Director, Workplace Technology & Digital Employee Experience, you will lead a large, distributed team responsible for delivering seamless technology experiences to employees nationwide, including senior leadership. You’ll oversee end-user support, endpoint engineering, collaboration platforms, service desk and field services, authentication and access, onboarding/offboarding, and experience analytics. Your mission: ensure both operational excellence and strategic innovation, fostering a culture of continuous improvement and employee-centric service.
Key Responsibilities
End-User Technology Operations: Oversee Service Desk & Field Services, endpoint engineering (Windows/macOS/iOS), device lifecycle management, authentication/access, printer and migration management, onboarding/offboarding, and remote support for offices without onsite staff.
Experience Measurement & Process Improvement: Lead the Digital Employee Experience (DEX) program, consolidate acquisition tech stacks, implement XLAs and experience analytics, monitor service queues and sentiment, and drive process standardization and tech stack alignment.
Executive-Facing Experience & Support: Deliver high-touch, proactive support for senior leadership, including dedicated resources and rapid response. Present DEX scorecards and improvement plans to C-suite and senior leaders.
Stakeholder Partnership & Change Leadership: Collaborate with People & Culture, Communications, and Business Units to improve onboarding, support key employee moments, and drive adoption of new technologies. Manage and govern vendor relationships (Ivanti, Microsoft, Apple, device OEMs,MSPs).
Lead employees across multiple locations, ensuring clear roles, career development, and succession planning.
WHO WE'RE LOOKING FOR
Bachelor’s degree in Information Technology, Computer Science, Engineering, or a related field required
ITIL v3 or v4 Foundation certification required
10+ years of experience in End‑User Computing, Digital Workplace, or a related technology field
5+ years of experience leading geographically distributed, multi‑disciplinary teams
Hands‑on leadership experience across enterprise IT service management and modern endpoint environments
Strong experience supporting Windows and Apple ecosystems, including SCCM, Intune, AutoPilot, and JAMF.
Proven ability to engage, influence, and communicate effectively with senior leaders and executives
Expertise in endpoint and device lifecycle management, authentication and access, onboarding and offboarding, and remote support models
Demonstrated vendor management and partner leadership experience.Strong people‑leadership skills, including coaching, talent development, and team performance management
Experience driving process improvement through service analytics, experience metrics, and data‑driven decision‑making
Ability to balance employee experience, operational reliability, security, and cost.
Experience enabling hybrid and remote work environments at scale.
Strong change leadership skills, including the adoption of automation and AI‑enabled capabilities
Comfortable presenting digital employee experience metrics, experience‑level agreements, and technology roadmaps.
Experience collaborating with HR, Employee Experience, Cybersecurity, Risk, Enterprise Architecture, and external vendors.
Ability to lead three direct reports and provide indirect leadership to approximately 20 team members.
Willingness to work in a hybrid environment with periodic travel and occasional after‑hours or weekend support as required.
NICE TO HAVE
Master’s degree in Technology Management, Information Systems,
or an MBA.15+ years of experience in End‑User Computing or Digital Workplace
leadership.10+ years of people‑management
experience.Experience with Ivanti HEAT /Ivanti ISM.
Advanced experience with Microsoft 365 and JAMF.Apple AC