Episode 258

#258 Alison Stewart: The LinkedIn Message That Changed Everything — Part Two

Published on: 27th March, 2025

Most people scroll through LinkedIn to procrastinate. Alison Stewart used it to land her next big thing. 

In Part One of this two-part series, Alison shared how she left her comfy finance job mid-pandemic to join a 16-person startup she found—wait for it—through networking online. Today, we dig into Overalls, the startup that thinks your benefits should actually benefit you. Novel, right?

Key Highlights of Our Interview:

Building a Village for Every Stage of Life

“Overalls is essentially your village… supporting you through life’s messier, more complex situations, like helping an elderly parent or finding summer camps for kids.”

A Rare Benefit That Earns Employee Appreciation

“This is one of the first times HR is getting thanked by employees for a benefit… they’re amazed at how thankful employees are for the support.”

Confidence in Uncharted Territory

“The biggest challenge was… do I have the skill set to do these things? Am I qualified to make some of these decisions?… In this environment, it’s all core because again, if you’re not doing it, it’s not getting done.”

Keep Your Goals in Sight: Write Them Down

“We can get distracted… By writing it down, being honest with ourselves, talking to others, that’ll help us hold ourselves accountable to what it is that we’re looking for.”

The Power of Focus and Manifesting the Right Move

“I wasn’t reaching out to a million people… I was focused, determined to put the time and energy in. My excitement led me to take a risk, and it worked.

_____________________

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Host: Vince Chan | Guests: Alison Stewart

 

--Chief Change Officer--
Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

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>>>180,000+ are outgrowing. Act Today.<<<

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Chief Change Officer™: Ensemble
A public town hall for change, power, and reinvention
Chief Change Officer™: Ensemble is the free, public edition of Chief Change Officer™, the Global Top 1% flagship podcast created and hosted by Vince Chan.

Built from Vince’s one-on-one interviews with global leaders, scholars, founders, authors, researchers, executives, and change-makers, Ensemble brings together a powerful collection of conversations on work, leadership, reinvention, ambition, identity, and the forces reshaping modern life.

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