Vince Chan
speaker
6,989 appearances
347 recordings
1 series
first heard Nov 2024
last heard Jun 2025
Vince Chan’s voice in public audio — every appearance, attributed to the second.
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Appearances
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.
Can you walk us through what happened then and how you used the platform to make a genuine connection
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 mass 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 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?
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 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?
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?
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?
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?
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