Matthew Bennett

Wildcard
DISC Type : sic

Vice President, Corporate Partnerships at Ottawa Sports and Entertainment Group (OSEG)

Canada

Overview

Matthew Bennett is the Vice President of Corporate Partnerships at Ottawa Sports and Entertainment Group (OSEG), where he leads revenue growth and strategic direction for the Ottawa REDBLACKS and Ottawa 67’s. A graduate of Brock Universitys Sport Management program, colleagues describe him as a "fantastic leader" and "true sales professional" who excels at building high-value relationships.

His career and academic background in sport management demonstrate a deep-seated passion for the sports industry. He translates this passion into his professional life by creating impactful partnerships and also shares his knowledge by teaching Sport Business Management to graduate students at Algonquin College.

He focuses on creating unique "money-cant-buy experiences" to provide partners with value that extends beyond traditional sponsorship.

Personality Overview

ROI Driven

Curious But Skeptical

Requires Proof

They typically tend to be late adopters even when they seem friendly and excited about what you have to sell  They are unlikely to ever become strong champions even when the conversations are going well; you should focus on cultivating other champions They are often friendly and nice, but can sometimes suprise you with their piercing questions

Topics They Care About

Strategic Partnerships
He architects multi-property sponsorship deals, recently extending major partnerships with brands like KPMG and Momentum Air Charter to enhance fan experiences.
Value-Driven Sponsorship
Believes in delivering measurable business impact and unique experiences for partners, ensuring they see tangible value from their investment.
Team Leadership
Emphasizes developing teams with a winning culture and is described by peers as an exemplary leader and mentor who elevates his team's performance.

Media Appearances

Matthew has no verified media appearances

Work History

11-2025
Vice President, Corporate Partnerships at Ottawa Sports and Entertainment Group (OSEG)
9-2023 - 11-2025
Vice President, Corporate Partnerships & Ticketing at Ottawa Sports and Entertainment Group (OSEG)
5-2022 - 9-2023
Vice President, Corporate Partnerships & Consumer Products at Ottawa Sports and Entertainment Group (OSEG)
8-2020
Part Time Instructor - Sport Business Management (Graduate Program) at Algonquin College of Applied Arts and Technology
8-2014 - 8-2015
Manager, New Business Development at Senators Sports & Entertainment

Education

2000 - 2004
Bachelor Sport Management from Brock University
2005 - 2007
MHK from University of Windsor

More Information

Social Presence :

Prographics :

Exp : 12 Location : Canada Job Level : Senior Designation : Vice President, Corporate Partnerships at Ottawa Sports and Entertainment Group (OSEG)
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Insights For Selling To Matthew

During A Call Or A Meeting

DO's

  • Share testimonials from known people and give multiple examples of product value
  • Focus on immediate action-items rather than the larger goals
  • Invite them for a social do but don’t rely solely on the relationship

DONT's

  • Don’t overhype the product/pitch, keep it measured
  • Don't ask them to move fast, let them take their time and digest all the information
  • Avoid phrases like ‘trust me’, ‘you will just love it’ etc.

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Matthew is

  • Clear proof of product value matters to them, followed by others' testimonials and rapport.
  • Will you ever get a clear answer from Matthew

  • They are likely to give you a clear answer without taking you around in circles. However, if you share a good relationship, they might not be so forthcoming.

Insights For Deal Planning

    How fast (or slow) will Matthew move?

  • They like to perform full analysis and can take time to make any decision.
  • Can Matthew take some risk or not?

  • They weigh all decisions systematically and are unlikely to take many risks.

You And Matthew

Personality Compatibility


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