Chris MacKinnon in

Chris MacKinnon

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Director of IT at Winnipeg School Division
📍 Winnipeg, Manitoba, Canada

Chris MacKinnon is a people-first IT Director at Winnipeg School Division with over 25 years of experience in sectors like education, healthcare, and retail. He focuses on aligning IT strategy with educational outcomes, modernizing infrastructure, and developing his teams potential. Chris is a 2019 CIO Leadership Award recipient and holds a Business Administration diploma from Red River Community College.

He is a reflective leader who values trust, vulnerability, and gratitude as foundational elements for effective teams. His personal philosophy emphasizes that leadership is built on small, consistent actions and that showing appreciation strengthens professional relationships. He believes in creating a supportive environment where people feel valued and empowered to grow.

In April 2025, he mentored students in a hands-on project to evaluate real-world cybersecurity contract proposals for the school division.

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Experience
13 Years
Current Role
Director of IT
Job Level
Mid-senior
Location
Winnipeg, Manitoba, Canada
Personality Overview

How Chris shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Chris cares about

People-First Leadership
Emphasizes empathy, trust, and vulnerability as core tenets of his leadership style, frequently writing about these concepts as essential for team success.
Educational Technology
As IT Director for Manitoba's largest school division, he is focused on aligning technology strategy with educational outcomes to support over 30, 000 students.
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Career

Work history

1-2024
Director of IT
Winnipeg School Division
8-2023 - 1-2024
Vice President Information Technology
Princess Auto Ltd.
11-2021 - 7-2023
Director, Information Services
Canadian Museum for Human Rights
4-2013 - 11-2021
Director Of Technology Services
Hanover School Division
4-2012 - 4-2013
I.T. Operations Manager
South Eastman Health
In the press

Media appearances

Winnipeg school division investigating explicitly altered images of students shared online. Featured in Global News
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Education
1992 - 1994
Business Admin
RRC Polytech
1992 - 1994
Business Administration Diploma
Red River Community College
Social presence
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Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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