#378 Alison Stewart: The LinkedIn DM That Launched a Startup—Part One
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What prompted Alison Stewart's career change?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist humility for change progressives in organizational and human transformation from around the world. Are you thinking about stepping away from corporate America? Or maybe you've already left. You are still trying to figure things out. If so, this episode is just for you. Today, I'm sitting down with Alison Stewart, who made the big shift from the stability of corporate life, specifically over 10 years in finance and insurance, to the chaotic world of new ventures. Her new baby focuses on redefining employee benefits and experiences. And she made this leap right in the middle of COVID. This is actually part one of a two-part series.
Today, we're diving into the personal changes Allison has experienced, her motivations, the steps she took, and her LinkedIn story of connecting with her current co-founder. Tomorrow, we'll talk about the new venture called Overalls, which is making waves in the employee benefits space. They're building a network of live concierge, including stay-at-home parents, the underemployed, and the 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 and building. Let's dive in.
Morning, Vince. Thanks for having me.
Alison works in the employer-employee space. Before we look into that, though, let's get to know her a bit better. Alison, tell us about your career journey, your evolution, and the transformations along the way. Then we'll explore different elements of what has brought you here.
Yeah, I'm Allison Stewart. I get to call Massachusetts home in the United States, just north of Boston. And my career has largely been focused in the insurance industry right out of college. I think I actually prioritized location over job, but moved to Washington, D.C., had a great group of colleagues and worked as the insurance broker. Didn't think that's what I wanted to do.
How did childhood experiences shape Alison's adaptability?
long term, spent about five years with that company and then went back to business school to figure out my next step. And from there, I took a really interesting internship, spent some time learning about coffee and doing marketing, had a lot of fun, but really found that I enjoy change. I don't want to be in a vertical in my career. I didn't want to grow up in a specific lane, which was the case at the company that I was working for in that marketing role, just continuing to only touch marketing. I found I really gravitated towards operational roles where you just naturally have your hands in more things. And so despite my best efforts after business school, I ended up back in the insurance industry at a large insurance carrier. That had this program where they took really talented folks and moved them around in an organization in an internal consulting role, which really helped feed that desire in me to keep learning and try different things. And so that was a really great experience. experience.
And through that, you know, my business unit was sold and I was introduced to a new company, another Fortune 100 company, very large environment and got to a point where I just felt like the impact I was having wasn't what I wanted it to be. Large companies are great. They offer a ton of benefits, but I really wanted to try to do something that was a little bit more risky. I wanted to find something that I could learn and grow faster. And that's how I ended up where I'm at today. I'm at a company called Overalls and we're an employer benefit personal assistant for the workforce. And I've been growing this company for the last three years and it's been amazing.
Earlier, you mentioned you actually enjoy change. We talked about growth, about risk. And I find it interesting because the show is called Chief Change Officer, where we dive into change from all angles, organizational, personal, and beyond. But when you say you enjoy change, let's be real, most of us enjoy change when we own it. when we are in control.
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Chapters
7 chapters
1
What prompted Alison Stewart's career change?
0:12–4:11
2
How did childhood experiences shape Alison's adaptability?
4:11–8:30
3
What challenges did Alison face during her career transition?
8:30–11:24
4
How did the COVID-19 pandemic influence Alison's decision?
11:24
5
What is Overalls and how is it redefining employee benefits?
3:09–7:07
6
What lessons did Alison learn from her corporate experiences?
7:07
7
How did Alison's networking strategy lead to her startup?
3:41–22:59
Speakers
1 identifiedMore from Chief Change Officer™: Ensemble
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