Chief Change Officer
#257 Alison Stewart: The LinkedIn Message That Changed Everything — Part One
Wed, 26 Mar 2025
Most people scroll through LinkedIn to procrastinate. Alison Stewart used it to land her next big thing. In Part One of this two-part series, Alison shares how she left her comfy finance job mid-pandemic to join a 16-person startup she found—wait for it—through networking online. We talk about career pivots, gut instincts, and how she slid into her co-founder’s inbox like a pro. Tomorrow, we dig into Overalls, the startup that thinks your benefits should actually benefit you. Novel, right?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 --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Why did Alison Stewart leave her corporate finance job?
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.
Chapter 2: How did Alison Stewart find her new opportunity during the pandemic?
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.
Chapter 3: What was Alison's career journey before joining Overalls?
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.
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Chapter 4: How did early life experiences prepare Alison for career transitions?
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.
And I think certainly that experience growing up has helped me really get excited and look forward to change in ways that I think some people around me are maybe more hesitant. And when we first started moving, I think the first two moves, I was hesitant and I had built great friends and I was very sad to leave them. But then once I got to the new community, I realized that I didn't have to
leave my old friends behind. I could still, this is before Facebook and all of the means of communication that we have today, but I was still able to keep in touch, writing letters, visiting friends, but at the same time build a new network and meet new people. And that was always very exciting to me or became very exciting to me through my experience moving around.
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.
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Chapter 5: What prompted Alison to pivot during the global health crisis?
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?
I realized that my time at those big companies, I had learned a ton, but I also started to see a bunch of patterns where you bring on some new leadership teams and we would almost have to take 10 steps backwards in order to move that step forward. And we were up. I helped to take that step when someone else came in and I just felt like I kept getting reset and it wasn't serving me anymore.
I needed something different. And I think during the health crisis, for me personally, it was this realization that things can change overnight. I never in a million years expected that we were going to basically not leave our homes for that first six months of the pandemic.
You wouldn't be able to see family and friends like that had never crossed my mind as something that would happen in our lives. And so having experienced that, I think in some ways you start to think about, well, what do I want to get out of my life? And am I getting that right now? And if not, what needs to change? And so I really went through the process.
a self-reflection process to understand what, how would I be fulfilled? Like, how could I be the best version of myself and where were the gaps and what did I need to do to make a change? So for me, I was fortunate enough that my husband and I both work full-time. And so I had a little bit of flexibility to make a decision and make a change and kind of
take a little bit of a risk in my next move, but also took the time to make sure it wasn't too much of a risk that if it failed, I would be in a position to bounce back. For me, the crisis and that change just was a wake-up call. That was like, Alison, you haven't really been fully fulfilled in this role for some time, and now's the time to make that change.
But one thing that I think I did that helped mitigate the risk of making a change is it wasn't just... Searching, skimming LinkedIn for jobs, reading all these job descriptions and being like, oh, yeah, I could do that job. I didn't wrote it as can I do this job and that that job is a better title, probably better salary. I can do it. Like, I want to apply for it because I know I can do that job.
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