Business Casual: The Stories We Tell, In and Outside of the Boardroom

My guest today is Jillian Kennedy, Chief Operating Officer at the CAAT Pension Plan. Jillian has spent over 25 years in the pension and financial services industry, building a career grounded in problem-solving, relationships, and a deep desire to help people navigate complex systems.

 

What I appreciate most about Jillian is her thoughtful and human-centered approach to both leadership and life. She brings clarity to complex topics like financial wellbeing, while also speaking candidly about the emotional realities that often go unspoken, including our relationship with money, self-doubt, and the pressure many women carry throughout their careers.

 

Some key takeaways from our discussion:

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• Our relationship with money is deeply emotional, and often shaped by experiences we do not openly talk about.

• Career journeys do not need to be linear. Thinking in “chapters” can create space for growth, reinvention, and self-compassion.  

• The most meaningful moments in life are often not measurable, but they shape who we become and how we lead.  

 

Please enjoy this thoughtful and energizing conversation with Jillian about financial wellbeing, leadership, and navigating life’s many chapters with curiosity and intention.  

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Connect with Jillian on LinkedIn​​

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Music: "Come Out Tonight" by Vicki Vox (via Epidemic Sound)