Kevin Jacobs

Pioneer
DISC Type : DIS

Strategic Advisor at Yolando

Toronto, Ontario, Canada

Overview

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. "

Personality Overview

Dynamic But Sincere

Decisive But Friendly

Driven But Considerate

They have the unique ability to win both love and respect from their team (or outsiders)  They combine a unique set of diverse traits where they are fast and friendly but can slow down to be thorough when needed If they are convinced, they can become very strong champions for your product

Topics They Care 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.
Reality TV Analysis
He co-founded "The Confessional" with Rob Has A Podcast, a newsletter and media project where he writes and speaks about the strategy behind popular reality shows.

Media Appearances

Kevin Jacobs - Enterprise Account Executive at Supermove - ZoomInfo. Featured in ZoomInfo

See Now

Work History

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

Education

Master of Information (MI) from University of Toronto
Bachelor of Arts (BA) from Western University

More Information

Social Presence :

Prographics :

Exp : 9 Location : Toronto, Ontario, Canada Job Level : Middle Designation : Strategic Advisor at Yolando
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Insights For Selling To Kevin

During A Call Or A Meeting

DO's

  • Ask them for a lunch or coffee once some rapport has been established
  • During followups, use calls or text if needed, they should be fine
  • Mostly stick to your standard pitch and qualifying script, but add some stories or anecdotes to it

DONT's

  • Avoid focusing only on the product or its ROI, keep building trust subtly
  • Don’t hesitate from asking questions or pushing them, but take a formal approach
  • Don't lean very heavily into providing too much information, sharing whitepapers etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Kevin is

  • Nothing less than a strong combination of proof of results, relationship and high levels of professionalism is effective with them.
  • Will you ever get a clear answer from Kevin

  • They can say no while staying friendly, but can also be pursuaded to reconsider

Insights For Deal Planning

    How fast (or slow) will Kevin move?

  • They are generally fast movers and can take quick decisions
  • Can Kevin take some risk or not?

  • They have high risk-appetite but can get ahead of themselves once in a while. Observe carefully

You And Kevin

Personality Compatibility


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