Chief Change Officer
#378 Alison Stewart: The LinkedIn DM That Launched a Startup—Part One
Sun, 18 May 2025
Not all career changes are dramatic. Some are deeply deliberate—and a little serendipitous.In Part One, Alison Stewart, COO of Overalls, walks us through her transition from 10+ years in the financial sector to co-founding a startup she discovered on LinkedIn. With two kids at home and a stable job in a Fortune 100 company, Alison didn’t jump recklessly. Instead, she asked the hard questions: Am I fulfilled? What do I want next? And how much risk am I really willing to take?This episode unpacks what happens when you combine career intuition with operational precision—and how a well-timed DM can change everything.Key Highlights of Our Interview:From Corporate Climb to Personal Wake-Up Call“Time started blending together during the pandemic. I had to ask: Am I actually happy? Or just coasting in a cycle of constant resets?”The Treadmill of Big Company Life“With every leadership change, we took ten steps back before we moved one forward. I was learning—but I wasn’t growing.”Childhood Moves, Adult Adaptability“Moving five times by age 14 taught me to see change as an opportunity. That mindset still guides me today.”The Pregnancy + Merger Combo“Just weeks before giving birth to my second child, my business unit was sold. The uncertainty could’ve been paralyzing—but I chose to treat it as a new beginning.”Risk—But Not Reckless: Mapping a Smarter Pivot“I didn’t quit cold. I asked: What am I good at? What fulfills me? What can my family support? I gave myself permission to explore—and permission to say no.”The Non-Obvious Job Search Strategy“Instead of applying for jobs I knew I could do, I reverse-engineered what I wanted: values, pace, purpose. I wasn’t chasing a title—I was chasing a fit.”The Moment Overalls Popped Off the Screen“When I read about Overalls, something clicked. I didn’t even know if they were hiring. I just knew I had to reach out.”Why LinkedIn Isn’t Just Noise“It wasn’t a random scroll. I used LinkedIn intentionally—to research, reflect, and eventually connect. That DM changed everything.”Communicating Across Industries“Moving out of insurance meant translating my skill set. I had to show how what I did mapped onto what I wanted to do.”Community + Clarity = Career Confidence“A networking group of MBA alumni helped me spot my own excitement. They said, ‘This one lights you up. Go for it.’ That feedback made all the difference.”____________________Connect with us:Host: Vince Chan | Guests: Alison Stewart --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: 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.
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Chapter 2: 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.
So tell me, what is it about change that resonates with you personally? I remember you once told me that growing up, you experienced quite a bit of change. Would you say those early experiences prepared you for all the transitions you've navigated as an adult?
Yeah, absolutely. So growing up, I moved around a good amount, nothing crazy. But between the ages of five and 14, I moved five times, moving from South and the United States to North, not cross country, not international, not these like crazy
Cultural changes, but these shifts where as an elementary school student, as a middle school student, as a high school student, very trying times or big developmental changes going on at that age and then having to navigate new communities, make new friendships.
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Chapter 3: What challenges did Alison face during her career transition?
And I do believe that's what has kind of shaped how I think about change and understanding that sometimes, as you mentioned, change happens to you and that is a very different experience than you driving and controlling that change. But I really think that it's a mindset shift. Change is being forced on you in some cases.
When I was at a company and my business unit got sold, that was a forced change. I didn't necessarily want to go to this new company. I wasn't sure if I was going to have a job at that new company. I was also pregnant with my second child. I gave birth a week after that deal had closed. So there was a lot of uncertainty and uncertainty.
It could have been a very trying time for me, but I always like to think that it's a new beginning. What good am I going to make out of this? How do I take control of the situation? Because I believe that there's always an opportunity to take control of the situation and help shape where it goes.
And I think a lot of that is from my experience moving around as a child, owning my new community, taking advantage of the opportunity to meet new people and explore new things.
It sounds like your childhood set the stage. You got used to going with the flow, adapting to new places and people, and it seems you even enjoyed it. But then, as you grew up, you took a more stable path. You went to business school, joined well-established companies like Wells Fargo, Liberty Mutual, and Lincoln Financial. You could have stayed on this secure track.
In fact, you did stay in the financial industry for about 10 years. But then you made a big change. during the once-in-a-lifetime global health crisis right around 2020. So what happened then? What was it about the environment or the timing that either pushed or pulled you towards making that change?
Yeah, that's a great question. I think a lot of people during that health crisis, during this pandemic, something we'd never seen before in our lifetime, felt like in some ways we were on a wheel, like every day, just time started blended together. And at one point I had to stop and say, what am I doing? What do I want to be doing? Am I happy?
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Chapter 4: How did the COVID-19 pandemic influence Alison's decision?
Chapter 5: What is Overalls and how is it redefining employee benefits?
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.
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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Chapter 6: What lessons did Alison learn from her corporate experiences?
Chapter 7: How did Alison's networking strategy lead to her startup?
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.
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.
So tell me, what is it about change that resonates with you personally? I remember you once told me that growing up, you experienced quite a bit of change. Would you say those early experiences prepared you for all the transitions you've navigated as an adult?
Yeah, absolutely. So growing up, I moved around a good amount, nothing crazy. But between the ages of five and 14, I moved five times, moving from South and the United States to North, not cross country, not international, not these like crazy
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