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 place.
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

**Base Salary:**CAD $0.00 - 0.00

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 ACSP or ACMT certification.
• Change management certification or experience using Prosci or ADKAR methodologies.

THE CULTURE We believe a career should be meaningful. Not just a means to earn a living. Our culture is one where everyone's voice is heard and valued. Because that’s what it takes to create better health for all. We dare to challenge the status quo. And we’re driven by people who have challenged theirs. We believe that your workplace should empower you to be the best version of yourself. That’s why we provide a place where you can be inspired, challenged, and rewarded.

Where your growth means our growth.
Where your voice is heard and valued.
Where your work has purpose. And purpose matters.

We believe our people are critical to our overall success. Inclusivity makes us a stronger, smarter and more informed organization. Being intentionally inclusive of diverse backgrounds, perspectives and experiences will enhance our company culture to positively impact how we support our communities. A career at GreenShield isn’t just about personal achievements, it's about making a difference together.

Here’s to Better Health for All!

A FEW MORE DETAILS Proficiency in English is required for this position. As part of this role, you will be required to communicate with colleagues or customers who use English as their primary language. By requiring English proficiency for this position, we aim to ensure that our employees can excel in their roles, collaborate, and communicate effectively, and contribute to the success of our organization.

GS supports diversity, equity and inclusion in our teams and communities, and we value the unique contributions made by all. Even if your experience doesn’t align perfectly to every requirement, we invite you to apply. We encourage applications from all candidates and will accommodate needs under human rights legislation throughout all stages of the recruitment and selection process. Please let us know of any accommodation through requestforaccommodation@greenshield.ca. Information received relating to accommodation will be addressed confidentially.

Providing this information gives GS consent to use your personal information to assess your suitability for specific positions, future opportunities or for your personnel file. Your résumé will be held in strict confidence and will be viewed only by the Organization. Information may be stored outside of Canada and could be used for aggregate statistical purposes (which uses no personal identification).

AI Usage - GreenShield leverages AI to help produce Job Descriptions, and ideate on interview questions. We also leverage AI for interview transcription support.