Overalls COO Alison Stewart: Would You Let Your Employer Do Your Laundry? – Part One

Part One.

Thinking about leaving Corporate America? Or maybe you’ve already taken the leap and are still navigating the journey? This episode is tailor-made for you.

Today’s guest, Alison Stewart, made a bold move from a decade-long career in finance and insurance into the fast-paced world of startups. A switch she made in the midst of the pandemic.

Even more inspiring? She landed this opportunity through networking on LinkedIn. While many of us turn to LinkedIn for job searches, skepticism around job postings is common.

This is actually part one of a two-part series.

Today, we’re diving into the personal changes Alison has experienced: her motivations, the steps she took, and her LinkedIn story of connecting with her current co-founder.

Tomorrow, we’ll talk about her new venture, Overalls, which is making waves in the employee benefits space. They’re building a network of “life concierges,” including stay-at-home parents, the underemployed, and retirees, and linking them with employers to help reduce the day-to-day stress on employees. Will this model make employees feel more loyal? More willing to return to the office? We don’t know yet, but it’s definitely an idea worth exploring.

Key Highlights of Our Interview:

"What Am I Doing?” – Hitting Pause on the Corporate Grind

“During the pandemic, time started blending together. I had to stop and ask, what am I doing? Am I happy?” Those months at home made me realize how I’d been running on autopilot, stuck in a cycle of new leadership teams and constant resets. With every change, it felt like we were taking ten steps back just to make one forward."

“The Safety Net of a Strong Company” – Navigating Stability vs. Fulfillment

“You can get caught up in…having a strong company, great group of colleagues…new opportunities coming at you. But it might not be what truly motivates you.”

“Controlling for Risk Factors” – Making Thoughtful Career Moves

“I was trying to control for those risk factors, or at least account for them…what was I comfortable with? How would it impact my family?”

“Overalls Caught My Eye” – The Power of an Unexpected Spark

“I was sitting at work…reading about the launch of Overalls, and I got really excited. People almost stopped me, saying, ‘Allison, nothing gives you as much excitement as this opportunity."

“Taking Skills Beyond Insurance” – Exploring New Industries on LinkedIn

“I was interested in exploring something outside the insurance industry…how does my experience, how do my skills translate, and how do I communicate them effectively?”

Connect with us:
Host: Vince Chan | Guests: Alison Stewart

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Chief Change Officer: Make Change Ambitiously.

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