Kevin Jacobs in

Kevin Jacobs

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Strategic Advisor at Yolando
📍 Toronto, Ontario, Canada

Kevin is an Enterprise Account Executive at Supermove with over a decade of experience in tech sales, focusing on helping moving companies grow. He holds a Master of Information from the University of Toronto. Colleagues often describe him as frank, transparent, intelligent, and solution-focused.

Outside of his tech career, Kevin is a master strategist and storyteller, known for his success on high-stakes competitive reality television shows. He actively analyzes game theory and decision-making through his writing and podcasting, connecting with a large community of fans and fellow strategists.

He is the winner of the 10th season of the reality show "Big Brother Canada. "

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Experience
9 Years
Current Role
Strategic Advisor
Job Level
Middle
Location
Toronto, Ontario, Canada
Personality Overview

How Kevin 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 Kevin cares about

Competitive Strategy
As the winner of "Big Brother Canada" and a contestant on "The Traitors Canada, " he is a proven master of high-stakes social and strategic gameplay.
Moving Industry Tech
His current role at Supermove is dedicated to providing technology that helps the largest moving companies in North America operate more efficiently.
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Career

Work history

1-2026
Strategic Advisor
Yolando
9-2025 - 12-2025
Contestant - Traitors Canada Season 3
Bell Media
1-2025
Enterprise Account Executive
Supermove
5-2024
Founder/Managing Editor - The Confessional
Rob Has A Podcast
4-2024
GTM Advisor
Maple
In the press

Media appearances

Kevin Jacobs - Enterprise Account Executive at Supermove - ZoomInfo. Featured in ZoomInfo
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Education
Master of Information (MI)
University of Toronto
Bachelor of Arts (BA)
Western University
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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