Cassandra Drake

Activist
DISC Type : Cd

Expert-in-Residence – Strategic Advisor at DMZ

Canada

Overview

Cassandra is an SMB Mentor and ex-Meta employee who transitioned from architecture to building impact-driven businesses. As an Expert-in-Residence at DMZ, she advises startups on digital marketing and growth, drawing from her experience incubating over 75 businesses. She is currently a Tech MBA candidate at the Schulich School of Business.

With a background in architecture, she possesses a strong aesthetic sense, praised by colleagues for her design skills in branding and graphics. She is also a partner in a functional beverage company, indicating an interest in wellness products. People who have worked with her describe her as brilliant, empathetic, and a master of "system thinking. "

She has supported over 1, 500 entrepreneurs in bringing their visions to life.

Personality Overview

Perfectionist

Value Conscious

Meticulous

They care equally about the product and its potential impact.  They respond well to confident salespeople. They focus on objectivity in a pitch and pay little attention to bells and whistles.

Topics They Care About

SMB Growth
As a mentor and consultant, she specializes in developing digital marketing and growth sales channels for small to medium-sized businesses.
Founder Mentorship
She founded The VIZION, a social enterprise and incubator lab dedicated to supporting visionaries and founders in building their businesses.
Early-Stage Investing
Serves as a Deal Partner at Boardy, where she helps connect founders with the right investors to secure funding.

Media Appearances

Cassandra Drake - Experts-In-Residence - DMZ Toronto. Featured in DMZ Toronto

See Now

Work History

8-2025
Expert-in-Residence – Strategic Advisor at DMZ
1-2026
Deal Partner at Boardy
4-2025
Partner at The World of Yasu
5-2021 - 1-2026
Director at The Vizion
4-2021 - 12-2023
Program Developer at The Vizion

Education

9-2025 - 12-2026
MBA - Tech & Leadership from Schulich School of Business - York University
2008 - 2012
Bachelor of Architectural Science (BArchSci) from Toronto Metropolitan University

More Information

Social Presence :

Prographics :

Exp : 4 Location : Canada Job Level : N/A Designation : Expert-in-Residence – Strategic Advisor at DMZ
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Insights For Selling To Cassandra

During A Call Or A Meeting

DO's

  • Get to the point quickly instead of spending too much time on pleasantries
  • Be crisp while making the pitch
  • Refer to testimonials from others in similar positions

DONT's

  • Do not give up if they are not convinced, try again with a different approach
  • Don’t try to be an alpha salesperson, give them equal space
  • Avoid long winding pitches, stay objective

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Cassandra is

  • Belief in the product plays an important role, followed by objective proof and testimonials.
  • Will you ever get a clear answer from Cassandra

  • They may hesitate slightly, but if they are not convinced, they will say no.

Insights For Deal Planning

    How fast (or slow) will Cassandra move?

  • Their decision making speed is somewhere in the middle.
  • Can Cassandra take some risk or not?

  • They can take risks only after they have analyzed the advantages and disadvantages.

You And Cassandra

Personality Compatibility


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