#379 Alison Stewart: Building a Life Concierge Startup From Scratch—Part Two
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What is the focus of Alison Stewart's startup, Overalls?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist community 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, in particular, over 10 years in finance and insurance, to the chaotic world of startups. Her new venture focuses on re-imagining employee benefits and experiences, as she made this leap right in the middle of COVID. This is actually part two of our two-part series.
Yesterday, we looked into the personal changes Alison has experienced, her motivations, the steps she took, and her LinkedIn story of connecting with the current co-founder. Today, We'll talk about this new venture, Overalls, which is making waves in the employee benefits space. They are building a network of live co-CH, 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 building and exploring. Let's get started. A few weeks ago, I released an episode with an executive coach.
We covered a lot and one of the things she shared was how some of her clients set up with the jobs, decided to move on. But then in a lot of cases, they ended up just trading one toxic boss for another. So clearly it wasn't the best move. Therefore, it highlights the importance of making career transitions thoughtfully and mindfully. You've also shared an interesting backstory with me about how you ended up at Overalls and how you connected with the co-founder through LinkedIn. These days, many people use LinkedIn for job searching but there's a lot of skepticism around job postings. Some of them are fake and networking can still hit or miss. But your experience was a real LinkedIn success story.
How did Alison transition from corporate life to a startup?
Can you walk us through what happened then and how you used the platform to make a genuine connection
Absolutely. So I'll start by saying I had already been thinking about my next project. move. I'd been scanning the LinkedIn jobs, trying to get a sense for what I thought was exciting about different jobs that I read and pulling out those pieces. What's going to do it for me? What's going to satisfy me? And at the same time, using my networks and actually talking to a group of alumni from my MBA program and listening to their stories about how they made job changes. At this point in my career, I'd been pretty squarely in the insurance industry, and I was interested in exploring something outside of the insurance industry, which I was thinking in my head, how does my experience, how do my skills translate, and how do I communicate those skills effectively when I'm talking to that next company? So I was doing my own scanning of
LinkedIn jobs, pulling elements from different job descriptions that were intriguing to me. And then also talking to my network, talking to folks in a very low risk environment about these types of job changes and what folks had done in the past. I was sitting at work one day and I got this newsletter in my inbox that was talking about the launch of Overalls. And I was reading about the company and the mission and I got really excited about it. And then I went on to LinkedIn to do some more research. I saw our CEO on LinkedIn and I happened to have my meeting that day with like my networking group. And I was talking to them about something that I'd come across this company about overalls. And people almost stopped me and they're like, Allison, it's very clear to me, like everything you've talked about up until this point, like nothing gives you like as much excitement as this. this opportunity. I didn't even know if it was an opportunity. I had just seen this company announced and thought, wow, that is what I'm looking for.
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Chapters
7 chapters
1
What is the focus of Alison Stewart's startup, Overalls?
0:12–4:32
2
How did Alison transition from corporate life to a startup?
4:32–10:03
3
What challenges did Alison face in her new role?
10:03–19:28
4
How does Overalls redefine employee benefits?
19:28–24:59
5
What mindset changes are necessary for startup success?
24:59–27:55
6
What advice does Alison have for aspiring entrepreneurs?
27:55–32:03
7
How does Alison maintain a hands-on approach in her role?
32:03–33:18
Speakers
1 identifiedMore from Chief Change Officer™: Ensemble
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