Michael Gladstone in

Michael Gladstone

Captain · DISC type DS
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

Long-Term Thinker
Consummate Professional
Dynamic But Sincere

They are very professional in their approach and can weigh multiple perspectives together. They might take some time to make their mind up but once they do, they don't change it easily. Reading between the lines and seeing beyond your words comes naturally to them.

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

No media yetWe could not find public media appearances for this person.
Education
MBA
Schulich School of Business - York University
BSc
York University
Education details unavailable
TanenbaumCHAT
Social presence
in
Behavioral profile

DISC profile (public)

D

Dominance (D)

Dominance (D) reflects how goal and task oriented a person is, and their ability to accomplish results irrespective of how demanding the circumstances might be. Those scoring high tend to be motivated by winning, competition, and success.

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