Jacqueline Dinsmore

Commander
DISC Type : D

Member at YPO

Greater Toronto Area, Canada

Overview

Jacqueline is the Managing Partner of Caravel Law and a serial entrepreneur, recognized as one of Canadas Top 25 Most Influential Lawyers. With a law degree from Western University, people she has worked with describe her as a strategic, precise, and natural leader. She excels in business development and legal consulting.

Outside of law, Jacqueline is a passionate supporter of female entrepreneurs. She is a board member for organizations like YSpace and Dovetail Community, which are dedicated to helping women scale their businesses. Her venture fund, Extra Innings Ventures, specifically invests in founders overlooked by traditional VCs.

Unique fact: She founded FlapJackKids, a successful childrens apparel company, which she grew and later sold.

Personality Overview

Strong-Willed

Decisive

Very Quick

They like to be in a position where they can control the conversation and terms.  They like to act fast and expect others to do the same. They are not focused on building rapport and relationships.

Topics They Care About

AI in Law
Actively speaks at events and participates in discussions about AI trends in the legal industry and the future of the billable hour, as shown in her recent activity.
Supporting Female Founders
Serves on the boards of YSpace (supporting the ELLA accelerator) and Dovetail Community, both focused on empowering women entrepreneurs.
Venture Investing
As a Founding Partner of Extra Innings Ventures, she invests in seasoned start-up founders who have been overlooked by traditional venture capital.

Media Appearances

Jacqueline has no verified media appearances

Work History

3-2025
Member at YPO
3-2024
Board Member at YSpace, York University
1-2024
Member of the Board of Advisors at Dovetail Community
3-2022
Founding Partner/Strategic Advisor at Extra Innings Ventures Inc.
6-2021 - 4-2023
Power of Her Impact Council Member at World Vision Canada

Education

1996 - 1999
LL.B from Western University
1992 - 1996
BAH from Queen's University

More Information

Social Presence :

Prographics :

Exp : 25 Location : Greater Toronto Area, Canada Job Level : N/A Designation : Member at YPO
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Insights For Selling To Jacqueline

During A Call Or A Meeting

DO's

  • Speak about competitive differentiation that your product offers
  • Make sure that you circle back fast on any action items, it wins their trust
  • Objectively showcase the impact that your product creates

DONT's

  • Don’t take too much time in sending them information if they ask for any
  • Do not back off when challenged, respond with a confident, objective answer instead
  • Don’t focus on process and rules, give the impression of being a ‘gets it done’ person

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jacqueline is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Jacqueline

  • If they are not convinced, they will have no hesitation in telling you the same.

Insights For Deal Planning

    How fast (or slow) will Jacqueline move?

  • They can take decisions very fast if you manage to convince them.
  • Can Jacqueline take some risk or not?

  • The risks don’t matter much to them.

You And Jacqueline

Personality Compatibility


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