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

Part Two.

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 two of a two-part series.

Yesterday, 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.

Today, 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:

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.”

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

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Chief Change Officer: Make Change Ambitiously.

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