Chief Change Officer
#379 Alison Stewart: Building a Life Concierge Startup From Scratch—Part Two
Sun, 18 May 2025
Overwhelmed by life? Alison Stewart gets it—and she’s building a startup to help fix it.In Part Two, the Overalls COO shares how her team is rethinking employee benefits by offering something surprisingly human: life support, literally. Whether it’s booking a plumber, navigating eldercare, or finding summer camps before the January rush, Overalls acts as a concierge for the chaos of modern life.Alison also opens up about what it really takes to scale an idea from zero—while trusting yourself to write the policies, run the ops, and still answer the phones. Spoiler: she’s done it all. If you’ve ever dreamed of building something meaningful from scratch, this is your operations masterclass.Key Highlights of Our Interview:What Overalls Actually Does (Hint: It’s Not Laundry)“We’re your life concierge—handling everything from vetting plumbers to eldercare planning. Our job is to give your time and sanity back.”The Startup Test: From Strategy to Scheduling Cleaners“Two weeks in, I was calling Colorado well inspectors, pitching insurance partners, and writing job descriptions. All in one day. That’s startup life.”Why a Stay-at-Home Mom Might Be Your Next Concierge“We tapped into an overlooked talent pool—retirees, caregivers, underemployed parents—and gave them flexible, meaningful work. It’s a win-win.”HR Is Finally Getting Thank-You Notes“Employers tell us: this is the first time employees are actively thanking HR for a benefit. That’s unheard of.”The Burnout Solution That Isn’t Therapy“Burnout isn’t always solved by meditation apps. Sometimes, it’s about having someone book that MRI or call the insurance company for you.”Confidence as a Startup Operator: Earning It Day by Day“Do I know how to write an HR policy? Not at first. But I figured it out. In a startup, everything’s your job.”Why Big Company Life Doesn’t Prepare You for This“In corporate, you focus on one slice. In startup life, you are the pie. You handle everything, whether or not you’ve done it before.”From Lean to Leveraged: Hiring with Intention“Writing job descriptions meant I could finally hire someone to take something off my plate. But no one else was going to write them.”Mindset Metrics (At Least in the Beginning)“Don’t just optimize for titles or compensation. Start with: What am I actually excited to build? What problem do I care enough to solve?”Advice for Fellow Change Progressives“Talk to people. Write it down. Be honest about what lights you up—and patient with the timeline. Growth is a slow burn. Trust it.”____________________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 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.
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Chapter 2: 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.
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 why.
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Chapter 3: What challenges did Alison face in her new role?
However, I would argue it's also about doing the proper work, figuring out what you really want, what aligns with your values, your interests, what doesn't. and being thoughtful about where you put your energy, rather than just casting a wide net. I'm curious, after you landed the role, what expectations did you have? Were you confident about the move? Or did you have a mix of feeling?
And now, after three years, Have those initial expectations been met or maybe even exceeded Did things turn out differently than you originally anticipated?
That's a great question. And I'm trying to think back to what those original expectations were. It feels so long ago. I think the biggest expectation was that I was going to build something to experiment and trip and get back up and do it again. The idea that I would have the ability to make some decisions, make some mistakes, and learn and grow from them very quickly in a short amount of time.
And so that's what I was most excited about and expecting in jumping from the large corporation into the startup environment was just that ability to learn quickly, get feedback on a decision, incorporate that feedback, and make changes quickly. I also was looking forward to rolling up my sleeves.
I think the biggest concern that the team had was, can I make this shift from this large corporation, which has a lot of things with a very cushy, there's lots of people that have different jobs. Can I jump into the startup and roll up my sleeves and be making these changes? strategic decisions, but also be like doing the job of the lowest level job in the company. Can you do it all?
But I was excited to do that because I'm the kind of person that loves to have my hands in different things and a variety of different things, which I think initially is what attracted me to operations is just the variety of work. So I was excited to take that. I was excited to roll my sleeves up. No task is beneath me. And that's still the case today.
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 PowerPoint. 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
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Chapter 4: How does Overalls redefine employee benefits?
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
that confidence and saying yes i am qualified to do all of these things and how do i fit them in and how do i prioritize them so that i'm being the most effective at my job and continuing to move at the pace that i want to move at so far we've explored many personal changes you've made in your life and now
You're building a venture that has the potential to create transformative change for others in the workforce. Let's dive into your current project. Overalls. What is the mission behind overalls? What specific problems are you tackling? And whose challenges are you aiming to resolve? You've told me before
about bridging the needs of employers with a valuable untapped talent pool that includes stay-at-home moms. Could you walk us through how Overalls is creating this connection and the potential impact it holds for both employers and individuals looking to reenter or redefine their roles in the workforce?
Yeah, so overalls were 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 someone
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 to do those things and and play phone tag but it needs to be done and and I would have better balance in my life and less stress if I was able to to take that off my list and 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 folks overall will take them off your plate, will be that extra set of hands for you.
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Chapter 5: What mindset changes are necessary for startup success?
They 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 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 overalls and what we were doing and the problems that we were solving. And it was getting folks really excited because they're like, oh, I've done this personally in my life for my family, or I have this background. These are the resources that folks should be using. And these are the questions they need to be asking.
I was like, wait, and you're looking for work. How can we. make this a win? How can I tap in on this wealth of knowledge that these folks have and better support my customers and then have those individuals, these stay-at-home parents, get value too and feel fulfillment? And this is it. We created this win environment. So now we have this network of
life experts, we call them, folks that are working for us in a flexible, part-time capacity, and they're getting to use their expertise, and they're working when they have the time in their schedule, extremely flexible, and they're helping people.
Because I get this great expertise, and they win because they're getting fulfillment, they're getting to use their background, and it's flexible and allows them to do everything that they were doing for their family.
So I'm really excited about everything that we're doing at Overalls, but for me, this network is one of the things that's near and dear to my heart as we scale our operation, but continue to provide this high level of service to our users.
So let's say I'm an employer running a firm with a team. that's juggling a lot of personal obligations and responsibilities along with their work. I come to you and you say, hey, we have a network of live experts. We call them live concierge who can take care of these things for your team.
By paying a fee, I'm able to offload some of these personal burdens from my staff, helping them stay focused, less distracted, and feel more supported at work. And because this is a benefit we as the employer provide, hopefully it fosters a greater sense of loyalty. Is that the core of the value prepositioned or am I missing anything here?
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Chapter 6: What advice does Alison have for aspiring entrepreneurs?
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 so thankful for the support you've been able to provide them. Going back to the pandemic, the world has changed dramatically.
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 upfront, 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, Alison, you, that
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 7: How does Alison maintain a hands-on approach in her role?
And as people, we're always reinventing ourselves and refining who we are. And so don't be afraid to do that and embrace the opportunities for learning and growth that come with change. And be patient with yourselves. These things, some changes are bigger and harder than others.
But I think having that time for self-reflection, viewing it as a learning opportunity and being patient ultimately will help you grow from that experience.
Absolutely. Being kind to ourselves is part of the process. Change doesn't happen overnight. and even if things don't fall into place right away, that doesn't mean they won't. I've learned the hard way too, being too tough on myself. Sometimes the best thing we can do is just be patient and allow things to unfold. Until next time, take care.