Chief Change Officer
#258 Alison Stewart: The LinkedIn Message That Changed Everything — Part Two
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 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.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: What is the focus of Part Two with Alison Stewart?
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.
Chapter 2: How did Alison Stewart transition from corporate to startup?
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.
Can you walk us through what happened then and how you used the platform to make a genuine connection
Chapter 3: How did LinkedIn play a role in Alison's career change?
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.
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.
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Chapter 4: What challenges did Alison face in a startup environment?
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
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Chapter 5: How does startup life differ from corporate work?
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. 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.
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.
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Chapter 6: What are the benefits and challenges of DIY in startups?
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, Allison. 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. 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, 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
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