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Careers aren’t ladders anymore, they’re portfolios, and if you’ve ever felt pressure to pick one lane, one identity, or one “clean” story, this episode is your permission slip. Trey Boynton, Chief’s Chief Diversity and People Officer, breaks down the rise of the multi-hyphenate leader and what the career ladder got wrong, why side hustles are a flex not a red flag, and how women are redesigning ambition without apologizing for it. You’ll leave with language to name your next “hyphen,” a grounded reality check on the “grass is grass” leap, and practical moves for managers who want to support non-linear growth without burnout or bias.
EMBRACE YOUR RANGE…
Women aren’t dialing back ambition.
They’re redesigning it.
New research with the Harris Poll shows 86% of women say they’re more ambitious now than they were five years ago. The difference? They’re building careers that don’t look like the traditional ladder.
This week, Trey Boynton from Chief joins us to unpack the rise of the multihyphenate leader — and what it means for individuals and organizations alike.
We get into:
• What the career ladder got wrong
• Why side hustles are a flex, not a red flag
• How community fuels ambition
• How to support non-linear growth without burning out top talent
Because ambition isn’t the problem.
The traditional career ladder is.
If you’re designing what’s next — for yourself or your team — this one’s a must.
About Trey Boynton: Trey has dedicated her decades-long career to creating change so that all people are valued, celebrated, and able to offer their unique contribution. As Chief Diversity & People Officer, Trey leads the People function and the Inclusion & Impact strategy for Chief. Her primary focus is to ensure equity and inclusion is embedded across the entire Chief ecosystem.
Prior to Chief, Trey was Senior Director of Inclusion & Collaboration at Cisco, managing a team dedicated to building and delivering on inclusion promises at scale. Prior to Cisco, Trey was the first head of diversity and inclusion for Duo Security. She began her career in higher education, holding multiple diversity & inclusion leadership roles at the University of Michigan, where she worked for more than 20 years. While at the University of Michigan, Trey received the Distinguished Diversity Leaders Award.
Trey attended Spelman College, has an undergraduate degree from Georgetown University and a graduate degree from the University of Michigan.
Learn more about Chief and connect with Trey Boynton
Disclaimer: This podcast is for informational purposes only and should not be considered professional advice. We are not responsible for any losses, damages, or liabilities that may arise from the use of this podcast. The views expressed in this podcast may not be those of the host or the management.
Connect with Us
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Mel Plett
CO- FOUNDER & CO-HOST
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Francesca Ranieri
CO-FOUNDER & CO-HOST
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Trey Boynton
Chief, Chief Diversity & People Officer