#149 Overalls COO Alison Stewart: Laundry, Leadership, and the Business of Caring – Part One

Are you ready to leap out of the corporate bubble? Alison Stewart sure was. In the midst of the pandemic, she swapped her steady finance career for the rollercoaster world of startups. Bold move, right? But what’s even more surprising is how she landed her new role—through LinkedIn networking! Yes, that LinkedIn. In this first episode of a two-part series, Alison shares her motivations for making the jump, the steps she took to get there, and how a simple LinkedIn connection led her to her current co-founder. In tomorrow’s episode, we’ll dig into her startup, Overalls, which is flipping the script on employee benefits. By creating a network of “life concierges” that includes stay-at-home parents and retirees, Overalls aims to reduce workplace stress and foster loyalty. Will it work? Tune in to find out. Key Highlights of Our Interview: "What Am I Doing?” – Hitting Pause on the Corporate Grind “During the pandemic, time started blending together. I had to stop and ask, what am I doing? Am I happy?” Those months at home made me realize how I’d been running on autopilot, stuck in a cycle of new leadership teams and constant resets. With every change, it felt like we were taking ten steps back just to make one forward." “The Safety Net of a Strong Company” – Navigating Stability vs. Fulfillment “You can get caught up in…having a strong company, great group of colleagues…new opportunities coming at you. But it might not be what truly motivates you.” “Controlling for Risk Factors” – Making Thoughtful Career Moves “I was trying to control for those risk factors, or at least account for them…what was I comfortable with? How would it impact my family?” “Overalls Caught My Eye” – The Power of an Unexpected Spark “I was sitting at work…reading about the launch of Overalls, and I got really excited. People almost stopped me, saying, ‘Allison, nothing gives you as much excitement as this opportunity." “Taking Skills Beyond Insurance” – Exploring New Industries on LinkedIn “I was interested in exploring something outside the insurance industry…how does my experience, how do my skills translate, and how do I communicate them effectively?” Connect with us: Host: Vince Chan | Guests: Alison Stewart ______________________ -- Chief Change Officer -- Change Ambitiously. Outgrow Yourself. Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs, Transformation Gurus & Bold Hearts. 6 Million+ All-Time Downloads. Reaching 80+ Countries Daily. Global Top 3% Podcast. Top 10 US Business. Top 1 US Careers. >>> 100,000+ subscribers are outgrowing. Act Today.<<< --Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Expansive Human Intelligence for 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.<<< <