Chief Change Officer - #258 Alison Stewart: The LinkedIn Message That Changed Everything — Part Two

Episode Date: March 26, 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 shared how she left her comfy finance job mid-pandemic to join a 16-person startup she found—wait for it—through networking online. Today, we dig into Overalls, the startup that thinks your benefits should actually benefit you. Novel, right?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 | 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.10 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>130,000+ are outgrowing. Act Today.<<<

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Oshul 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're 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. And she made this leap right in the middle of COVID. This is actually part two of our 2-part series. Yesterday, we looked into the prognosis changes Alison has experienced, her motivations, the steps she took, and her linked-in story of connecting with the current co-founder. Today, we'll talk about this new venture overalls,

which is making waves in the employee benefit space. They are building a network of live co-siesh, 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 sat up with their jobs, decided to move on, but then in a lot of cases, they ended up just trading one toxic balls 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 Overall's 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. 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 gonna do it for me? What's gonna 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, that you need to pursue this. And I was like, there's nothing 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 when Stently, 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. I think for me, what was very different is I was very deliberate about my reach out. I wasn't reaching out to a million people. I didn't do my job. I didn't drop my resume at thousands of LinkedIn jobs. I took that time to be focused.

And yes, I got a little lucky. Not everyone's going to respond to messages. But I think, I still believe in some ways I made it happen. I manifested it. I was focused, determined to put the time and energy in. And I think my excitement led me to do something I wouldn't have to take a risk. Seems like a silly risk to send someone out on LinkedIn,

but to me it felt like a big step to reach out to a stranger to comment on their business, but it worked. That's really encouraging to hear, though I completely agree. A lot of messages on LinkedIn go unanswered. And honestly, I don't respond to every message myself, because you can usually tell when it's just a generic Moz marketing message. But yes, luck, in quotation, is often what we call it when something just clicks in an almost magical way. However, I would argue it's also about doing the prep 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 feelings? 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 expecting and 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. 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, can I jump into the startup and roll up my sleeves and be making these 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. I weeks into the 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 the 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 a hundred percent, 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 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. It's like, 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? 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. 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 an adventure, 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, it's 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. 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 out 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 like 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 that 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 in 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 piece that I want to move at. So far, we've explored many personal changes you've made in your life.

And now you've built an adventure 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 OverRoles is creating this connection and the potential impact it holds for both employers and individuals looking to re-enter

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 is 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 folks. Overalls 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? 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. Where 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 the village. Everyone needs a village. I've got three kids, three young kids, so I live by the phrase, it takes the village. And I think overalls is part of our users' village. And all stages of life need a village. You need a support system, a friend, family, an 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 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 how 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, which 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 greatest sense of loyalty. Is that the core of the value propositioned or am I missing anything here? No, it's exactly that. It's the productivity back 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 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 at all, and we can help you. To web 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 an other 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, Allison, 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, talking to others about your goals really helps you realize them and write them down because we can get distracted. We can see a shiny carrot and start following it and then realize once we're too deep that, well, this wasn't exactly what we were looking for. So 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. And then I think as we approach any life change, it's all about the mindset. And to me, I truly believe that everything we tackle in life is a learning opportunity.

And you were just saying this, we started talking about stretching to the limits and going beyond the limits. I think it's really just redefining the limits, right? Like changing them. What our limits are today are not what our limits can be a year from now. And so I think about every step in life as a new learning opportunity, an opportunity for you to get to know yourself better. 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 the things don't fall into place right away. That doesn't mean they won't. I've learned the hard way to being too tough

on myself. Sometimes the best thing we can do is just be patient and allow things to unfold. If you like what you heard, don't forget to subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host. Until next time, take care.