Chief Change Officer
#60 Overalls COO Alison Stewart: Would You Let Your Employer Do Your Laundry? – Part Two
Fri, 01 Nov 2024
Part Two. Thinking about leaving Corporate America? Or maybe you’ve already taken the leap and are still navigating the journey? This episode is tailor-made for you. Today’s guest, Alison Stewart, made a bold move from a decade-long career in finance and insurance into the fast-paced world of startups. A switch she made in the midst of the pandemic. Even more inspiring? She landed this opportunity through networking on LinkedIn. While many of us turn to LinkedIn for job searches, skepticism around job postings is common. This is actually part two of a two-part series. Yesterday, we’re diving into the personal changes Alison has experienced: her motivations, the steps she took, and her LinkedIn story of connecting with her current co-founder. Today, we’ll talk about her new venture, Overalls, which is making waves in the employee benefits space. They’re building a network of “life concierges,” 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 exploring. 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: Make Change Ambitiously. Experiential Human Intelligence for Growth Progressives Global Top 3% Podcast on Listen Notes World's #1 Career Podcast on Apple Top 1: US, CA, MX, IE, HU, AT, CH, FI, JP 2 Millions+ Downloads 50+ Countries --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.20 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1% Podcast.Top 5 US Business.Top 1 US Careers.>>>180,000+ are outgrowing. Act Today.<<<See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Chapter 1: What inspired Alison Stewart to leave corporate America?
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?
Chapter 2: How did Alison connect with her co-founder on LinkedIn?
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 opportunity.
I didn't even know if it was an opportunity. I had just seen this company announced. 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 a 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.
But coincidentally, they have a job open. They're trying to round out the founding team and find their head of operations. And based on my background, he thinks I could be a good fit and asked me if I'm interested in applying. And the rest is history. I applied and now here I am. Three years later, chief operating officer.
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Chapter 3: What are the expectations of transitioning from corporate to startup?
partner about how we're going to get there be a strategic partner and get them on our platform then i went in to create some job descriptions of the roles that i needed to fill and they're like you did all of that in one day so you were boots on the ground making calls to local providers on behalf of your end customer and then you were building strategic partnerships with insurance carriers to be part of your product
And you were writing job descriptions for your team so that you could start hiring folks. Yeah, all of that in one day. And that's just something that wouldn't happen somewhere else, or at least in my roles in the bigger companies, because you have different departments that handle each of those tasks. And so to me, that was really exciting and energizing to be able to
be a part of it at all levels, be a part of this company and build it up. So that was a big expectation going into it. That still holds three years later. We've gotten bigger. We've had great market traction. I'm very excited about where the company is going. Still try to really be engaged at all levels.
If I've got team members that are fulfilling a customer's request, helping them with a life hassle, I'll take some of those on too. I want to make sure like what's happening with our user base. 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.
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Chapter 4: What challenges did Alison face in her new role?
Chapter 5: How does Overalls redefine employee benefits?
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. Now 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.
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 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 opportunity.
I didn't even know if it was an opportunity. I had just seen this company announced. 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.
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Chapter 6: What advice does Alison give for career transitions?
We're still a very lean team and that's been fun. Two weeks into that role, I was talking to an old colleague and they're like, so what's your day like? Before my day was spending a lot of time tweaking a PowerPoint presentation for a leadership meeting coming up in two weeks. In a startup space, we're not really using PowerPoints. We're using what we have.
We're not spending the time to make anything excessively pretty because it's not adding any value. It's getting it down on paper and sharing the story, but not having to do it to that extent because we're moving fast and we're making decisions with 80% of the information because you're never going to have 100%. You're never going to have perfect data.
But I was talking to my friends two weeks into the role and they're like, oh, what did you do today? And it was right when we were rolling out our hassle helper, life concierge service. And I took a request and I was, oh, yeah, I called some well inspectors in Colorado because someone was trying to close on a home. And then, you know, I was talking to an insurance agent.
partner about how we're going to get there be a strategic partner and get them on our platform then i went in to create some job descriptions of the roles that i needed to fill and they're like you did all of that in one day so you were boots on the ground making calls to local providers on behalf of your end customer and then you were building strategic partnerships with insurance carriers to be part of your product
And you were writing job descriptions for your team so that you could start hiring folks. Yeah, all of that in one day. And that's just something that wouldn't happen somewhere else, or at least in my roles in the bigger companies, because you have different departments that handle each of those tasks. And so to me, that was really exciting and energizing to be able to
be a part of it at all levels, be a part of this company and build it up. So that was a big expectation going into it. That still holds three years later. We've gotten bigger. We've had great market traction. I'm very excited about where the company is going. Still try to really be engaged at all levels.
If I've got team members that are fulfilling a customer's request, helping them with a life hassle, I'll take some of those on too. I want to make sure like what's happening with our user base. 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.
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Chapter 7: How does the startup environment differ from corporate life?
Yeah, so overalls, we're an employee benefit, and we help everyone. So we sell into the employer channel, so that means Generally, our end users are employees of that company. So much like they consume health insurance, they are consuming their overall benefit. At its core, we exist to help reduce the mental load, relieve stress, and give you time and energy back.
So think of us as your personal assistant. So I like to say that overalls as a personal assistant for the workforce. For everyday life hassles, like I need to find a plumber. I've had a leaky faucet, but I don't have time in my day to call three different plumbers to understand pricing, to get them to come out to the house. I'd have to take a day off of work to do those things and play phone tag.
But it needs to be done and I would have better balance in my life and less stress if I was able to take that off my list. And so that's the type of task that you can send to the overalls like concierge. So those types of tasks to planning a birthday, finding summer camps for kids, which is a very exhausting process. And you have to start in January for July and June. It's crazy.
But all of these things are like weighing down kids. folks overall will take them off your plate, will be that extra set of hands for you. But also bigger life milestones, a little bit more like messy, complicated situations that you don't know how to navigate on your own and you could use
an advocate a trusted friend for things like you've got an elderly parent do they need to go into assisted living or should they be doing home health care what will medicare pay for how do you fund these things what's best for your family and how do you understand the resources out there that are available to you so we come in there too so we a fairly broad solution but
trusted friend, your neighbor, your advocate, working through life with you, believing that stress and helping you achieve productivity at work and at home, having that time with your family that Everyone's goal, achieving that work-life balance. We're essentially, overalls is your village. Everyone needs a village. I've got three kids, three young kids.
So I live by the phrase, it takes a village. And I think overalls is part of our user's village. And all stages of life need a village. You need to support system, friend, family, and advocate. And that's what we're here to do. But one way that we're doing it, and you had mentioned some of the stay-at-home parents,
Early on, I have friends that have left the workforce, and I was talking to them about overalls, and they wanted to get back in and use their backgrounds in finance, in home health care. They've spent a lot of time in the workforce and left to take care of kids or elderly family members, and they wanted to get back in. But most traditional jobs...
Yeah, have a strict schedule, whether you're working 40 hours a week or part time, you have a set hours that you need to work and that doesn't work for everyone. And so I was talking to a few folks in my network about
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