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Certified

Jen Couldrey

Location

  • Toronto, Canada
I help entrepreneurs and their leadership teams run a better business AND live a better life

Meet Jen Couldrey

  • 15+ years as an entrepreneur & coach
  • Facilitated 550+ meetings and workshops
  • Create safe spaces where hard conversations build stronger teams
  • Named one of the Top 100 Most Powerful Women in Canada
  • Love helping good people build great businesses
  • Champion for building an intentional life that you love

Book Your Free Introductory Call

Ready to get more of what you want from your business? Let’s talk. Book your free introductory call with me to share your business needs and challenges. I’ll share my background and style. No pressure, just a real conversation to see if we’re the right fit.

My Approach

Energetic
I show up with a passion for EOS and for helping YOU get what you want. I am humbly confident, knowledgeable, organized, easy to work with- and love to have FUN in the session room
Psychological Safety
I create an environment where everyone on the team brings their full self so we can get the real issues on the table, address them directly and compassionately, and build a better future
Challenge Respectfully
I fight for you to be your best and get what you want: which means I'm equal parts cheerleader and accountability partner. You don't hire a coach to feed you cake (unless we're celebrating!)

What It’s Like to Work With Me

Hear from the business leaders and teams I’ve had the privilege of guiding through their EOS journey.

Client Success Videos

My Expertise & Insights

Insightful guidance, practical tips, and real-world stories to help you strengthen your leadership team and run a better business.

From Lion to Lamb & Back Again

In most of North America, the saying goes that March comes in like a lion and out like a lamb. For many entrepreneurs, this phrase holds a parallel to their business experience....
Read More

Speaking Engagements

I deliver keynotes and workshops that are perfect for groups of growth-oriented business owners and leaders. These fun, energetic, hands-on sessions will teach you practical tools that will help you:
  • Understand the 6 keys to building a truly great organization
  • Roll up your sleeves and confront your organizational issues head-on
  • Learn how to get everyone focused on achieving a clear company vision
  • Address the people issues causing you headaches
  • Understand how to instill discipline and accountability throughout your organization
  • Improve your own implementation of EOS

My Upcoming Events

There are no current upcoming events. Please check back regularly and follow us on social for the latest news and events!

Certified Implementer

jen.couldrey@eosworldwide.com

Phone: (647) 961-5889

  • Toronto, Canada

About

I know what it feels like to build something meaningful – and what it feels like when it isn’t working.

As a lifelong entrepreneur, I’ve experienced both the pride and the frustration that come with leading a growing organization. For over 15 years, I’ve helped leadership teams navigate those same moments- turning chaos and overwhelm into clarity and control.

My journey before EOS includes:

  • Leading and bringing dozens of ventures to life- from businesses to non-profits to live theatre shows
  • Helping leadership teams translate strategy to execution at Deloitte
  • Supporting hundreds of tech founders scale purpose-driven businesses at The Upside Foundation

Through more than 550 meetings and workshops facilitated and 1,400 leaders coached, I’ve seen what happens when good people align around a clear vision, execute with focus and discipline, and build a healthy team dynamic – and what happens when they don’t.

Today, I help entrepreneurial leadership teams master a simple, proven system to clarify their vision, gain traction, and become healthy, functional, and cohesive. I bring both structure and empathy into every session- helping teams build discipline and accountability without losing heart or humanity.

I love coaching leaders who are willing to be open, honest and vulnerable, who are ready to have hard conversations and make tough calls, and commit to doing what it takes to achieve their goals. I work with people who are ready to work ON the business instead of always being IN the business.

If you’re ready to break through the ceiling, regain control, and build a business- and a life- that you love: let’s talk.

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