Chief Change Officer
#150 Overalls COO Alison Stewart: Laundry, Leadership, and the Business of Caring – Part Two
Sun, 26 Jan 2025
Are you ready to leap out of the corporate bubble? Alison Stewart sure was. In the midst of the pandemic, she swapped her steady finance career for the rollercoaster world of startups. Bold move, right? But what’s even more surprising is how she landed her new role—through LinkedIn networking! Yes, that LinkedIn. In the last episode of a two-part series, Alison shared her motivations for making the jump, the steps she had taken to get there, and how a simple LinkedIn connection had led her to her current co-founder. In today’s episode, we’ll dig into her startup, Overalls, which is flipping the script on employee benefits. By creating a network of “life concierges” that includes stay-at-home parents and retirees, Overalls aims to reduce workplace stress and foster loyalty. Will it work? Tune in to find out. 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 ______________________ --Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs, Transformation Gurus & Bold Hearts. 6 Million+ All-Time Downloads. Reaching 80+ Countries Daily. Global Top 3% Podcast. Top 10 US Business. Top 1 US Careers. >>>100,000+ subscribers are outgrowing. Act Today.<<< --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 motivated Alison Stewart to leave her corporate career?
Chapter 2: How did Alison use LinkedIn to connect with her co-founder?
Absolutely. So I'll start by saying I had already been thinking about my next 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 had 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 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. It could use my insurance expertise, but it's in a startup environment and would help me make that transition into a more innovative space. And everyone was like, you need to pursue this. And I was like, there's something out there.
But I was thinking about Just reaching out to the CEO on LinkedIn to see if potentially he had some time to chat. It was silly. I'd never done anything like this before. But my network was like, absolutely. And they had just described some wild tactics that they had used to get attention in a job market. And I wasn't even looking for a job in my initial outreach.
I just wanted to understand if he had any time to chat through like how he got to this place in his career journey. Like if he had any insights or lines, if he was willing to share 10 minutes of his time. But I saw we had some mutual connections and I had read up on the company and it came out of a venture studio and did some reading there. And then I sent him a message.
I messaged him on LinkedIn. I've never done that before to anybody. It was the big crazy step for me. I was like, what do I have to lose? I'm just going to send him a message. I'm excited. I think this is a cool company. Worst case, I've shared that excitement and nothing happens. Fast forward two days and I get a note back from him and he doesn't have time to chat. He's very busy.
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Chapter 3: What challenges did Alison face transitioning to a startup?
In a big corporation, you focus on your specific role, whether it's creating a product, designing a strategy plan, or leading a team, and the brand, sales, and marketing machinery are already setting up, and the brand, sales, and marketing machine are already set up and running. All the support systems are in place. You don't have to worry about things like booking a travel or securing deals.
It's all handled by specialized teams. But when you are in a venture, even if you are the CEO of a well-funded startup, you are rolling up your sleeves and getting hands-on with almost every part of the operation. This change isn't just about the practical changes or even financial adjustments. Like a pay cut is a complete shift in mindset.
Losing the built-in support systems and having to figure out how to DIY do-it-yourself everything requires a different approach. And it's not a simple shift to make. Back to you, Alison, have you experienced this yourself? Maybe at the start of your venture journey? And if so, how did you adjust to that shift from everything taken care of to everything you have to take care of?
Yeah, that's a good question. I definitely experienced it, but I think I saw it as a positive and a welcome change. There was less red tape. You didn't have as many layers of approval or you weren't waiting on other people to make decisions or do that other job.
pros and cons right because if you're not doing it no one else is doing it so if i didn't make the time to write the job descriptions i was never going to be able to hire someone to help free up my time because no one else is there to write the job descriptions i think the biggest challenge that i experienced with it was do i have the skill set to do these things am i qualified
To make some of these decisions, I think that's one thing that I've had to grow and learn is to just trust myself there and know that I can do those things. I was not regularly doing them in my role before because there were other teams to do them. And I've always been one excited to roll up my sleeves. So I had no problem jumping in and doing those things. For me, it was more of the confidence.
We don't have an HR policy today. We need one. How do I go about creating one? What resources can I lean into? What makes a good job description? How do I prioritize the time to do some of those tasks that felt less core to my role? In this environment, it's all core. Because again, if you're not doing it, it's not getting done. And that was the biggest shift.
So if you knew, if I knew that I needed this job description in place or a decision on which customer servicing technology we were going to use in order to build and execute on my strategy, I knew I also had to make those decisions, have those conversations with different technology vendors, vet that process because there's no one else to do it.
And so it's exciting, but it becomes more of a game of, prioritization and how do we prioritize all of those different tasks and make progress and check things off the ever-growing list. I personally love the variety of the list. For me, the biggest challenge was
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Chapter 4: How did Alison's expectations change after joining Overalls?
no it's exactly that it's the productivity backs for the employer gets a more productive employee a more engaged employee and the employee has less stress they're getting things done when they get home at night back to their family they don't have to then worry about all of this their life to-do list they have someone taking care of it they can
truly unwind and enjoy that time with their family and employers are telling us in our check-ins with them that this is one of the first times they have employees coming up to them and thanking them for a benefit generally hr they're the unsung heroes in an organization and so they're amazed our employees are are so thankful for the support you've been able to provide them going back to the pandemic the world has changed
so much since 2020. And I think more than ever, we're asking our employees, we're asking members of society to do more and more with their time than they've ever been asked to do before. And we're seeing it. We're seeing this mental health crisis.
And I truly believe that we can help combat that at overalls by taking some things off your plate, helping acknowledge that these things are hard to try to do it all and we can help you.
To wrap up our conversation, which I've really enjoyed, I see you as what I would call a change progressive. Not just someone who embraces change, but someone who moves beyond their conventional framework and stretches beyond their comfort zone. That's the mindset I want to cultivate in my listeners too. I consider myself a change progressive as well.
It's about recognizing that our limits aren't really limits, but points we can push past to grow and improve. So to close, what advice would you give to people who are like you, either considering or in the middle of a transition from a stable, traditional environment to something new
such as adventure, a solo path, or another big change, how can they better prepare themselves to succeed in this kind of transformative journey?
Yeah, great question. I think starting off, like taking that time up front, doing that self-reflection and being honest with yourself on what you're looking for and talk to other people about it so that they can keep you honest too. So if you start making a decision, they can be like, wait, Allison, you...
this job that you're talking about does not align with what you were telling me you're looking for. Because sometimes we need that too. We need people to hold us accountable. So for me, it's taking that time up front. I think I would recommend everyone does for self-reflection, being honest with yourself.
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Chapter 5: What is the role of a COO in a startup?
Chapter 6: How does Overalls support employees in their personal lives?
And so I still try to make time to allow for that variety of activity because to me, I think that's what helps me keep a pulse on where we're going. And if I've made the right decisions and if we need to pivot, how do I get those learnings quickly and address them quickly?
You bring up such a valid point, especially for those with a deep corporate background transitioning into the venture world. I remember going through a similar experience myself, changing from a world where everything is already structured and taken care of to one where suddenly you have to take care of everything.
In a big corporation, you focus on your specific role, whether it's creating a product, designing a strategy plan, or leading a team, and the brand, sales, and marketing machinery are already setting up, and the brand, sales, and marketing machine are already set up and running. All the support systems are in place. You don't have to worry about things like booking a travel or securing deals.
It's all handled by specialized teams. But when you are in a venture, even if you are the CEO of a well-funded startup, you are rolling up your sleeves and getting hands-on with almost every part of the operation. This change isn't just about the practical changes or even financial adjustments. Like a pay cut is a complete shift in mindset.
Losing the built-in support systems and having to figure out how to DIY do-it-yourself everything requires a different approach. And it's not a simple shift to make. Back to you, Alison, have you experienced this yourself? Maybe at the start of your venture journey? And if so, how did you adjust to that shift from everything taken care of to everything you have to take care of?
Yeah, that's a good question. I definitely experienced it, but I think I saw it as a positive and a welcome change. There was less red tape. You didn't have as many layers of approval or you weren't waiting on other people to make decisions or do that other job.
pros and cons right because if you're not doing it no one else is doing it so if i didn't make the time to write the job descriptions i was never going to be able to hire someone to help free up my time because no one else is there to write the job descriptions i think the biggest challenge that i experienced with it was do i have the skill set to do these things am i qualified
To make some of these decisions, I think that's one thing that I've had to grow and learn is to just trust myself there and know that I can do those things. I was not regularly doing them in my role before because there were other teams to do them. And I've always been one excited to roll up my sleeves. So I had no problem jumping in and doing those things. For me, it was more of the confidence.
We don't have an HR policy today. We need one. How do I go about creating one? What resources can I lean into? What makes a good job description? How do I prioritize the time to do some of those tasks that felt less core to my role? In this environment, it's all core. Because again, if you're not doing it, it's not getting done. And that was the biggest shift.
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