Michael Gladstone in

Michael Gladstone

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Principal at PinnacleCIO
📍 Greater Toronto Area, Canada

Michael Gladstone is the Principal of PinnacleCIO, providing technology leadership and advisory services to small and medium-sized businesses. An MBA graduate from the Schulich School of Business, he specializes in IT strategy, software implementation, and cybersecurity. He also serves as a Part-time Professor at George Brown College.

His firm, PinnacleCIO, was recently nominated for a CanadianSME Small Business Magazine award for Best Professional Services provider for 2024.

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Experience
27 Years
Current Role
Principal
Job Level
Senior
Location
Greater Toronto Area, Canada
Personality Overview

How Michael 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 Michael cares about

SME Tech Challenges
He recently published an article in CanadianSME Small Business Magazine detailing solutions for the four biggest technology challenges that small and medium-sized enterprises face.
Digital Adoption
As an approved Digital Advisor for the CDAP and DMAP programs, he guides businesses in adopting new digital technologies to improve their operations and foster growth.
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Career

Work history

6-2020
Principal
PinnacleCIO
2-2025
Technology Strategist & Fractional CIO Services
Differly Inc.
1-2025
Parttime Professor
George Brown College
1-2015 - 6-2020
Director, Information Systems & Technology
Condrain Group
7-2010 - 9-2014
Chief Information Officer & Executive Vice President
IIBA
In the press

Media appearances

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Education
MBA
Schulich School of Business - York University
BSc
York University
Education details unavailable
TanenbaumCHAT
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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