#378 Alison Stewart: The LinkedIn DM That Launched a Startup—Part One

Not all career changes are dramatic. Some are deeply deliberate—and a little serendipitous. In Part One, Alison Stewart, COO of Overalls, walks us through her transition from 10+ years in the financial sector to co-founding a startup she discovered on LinkedIn. With two kids at home and a stable job in a Fortune 100 company, Alison didn’t jump recklessly. Instead, she asked the hard questions: Am I fulfilled? What do I want next? And how much risk am I really willing to take? This episode unpacks what happens when you combine career intuition with operational precision—and how a well-timed DM can change everything. Key Highlights of Our Interview: From Corporate Climb to Personal Wake-Up Call “Time started blending together during the pandemic. I had to ask: Am I actually happy? Or just coasting in a cycle of constant resets?” The Treadmill of Big Company Life “With every leadership change, we took ten steps back before we moved one forward. I was learning—but I wasn’t growing.” Childhood Moves, Adult Adaptability “Moving five times by age 14 taught me to see change as an opportunity. That mindset still guides me today.” The Pregnancy + Merger Combo “Just weeks before giving birth to my second child, my business unit was sold. The uncertainty could’ve been paralyzing—but I chose to treat it as a new beginning.” Risk—But Not Reckless: Mapping a Smarter Pivot “I didn’t quit cold. I asked: What am I good at? What fulfills me? What can my family support? I gave myself permission to explore—and permission to say no.” The Non-Obvious Job Search Strategy “Instead of applying for jobs I knew I could do, I reverse-engineered what I wanted: values, pace, purpose. I wasn’t chasing a title—I was chasing a fit.” The Moment Overalls Popped Off the Screen “When I read about Overalls, something clicked. I didn’t even know if they were hiring. I just knew I had to reach out.” Why LinkedIn Isn’t Just Noise “It wasn’t a random scroll. I used LinkedIn intentionally—to research, reflect, and eventually connect. That DM changed everything.” Communicating Across Industries “Moving out of insurance meant translating my skill set. I had to show how what I did mapped onto what I wanted to do.” Community + Clarity = Career Confidence “A networking group of MBA alumni helped me spot my own excitement. They said, ‘This one lights you up. Go for it.’ That feedback made all the difference.” ____________________ Connect with us: Host: Vince Chan | Guests: Alison Stewart   --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.<<< See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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What’s Stopping You from Outgrowing Yourself? Change Ambitiously. Outgrow Yourself. Chief Change Officer isn’t just another podcast. It ranks in the Top 3% globally, hit #1 in Careers (US), and cracked the Top 10 in Business (US)—because it offers what others don’t: expansive human intelligence, shared by the world’s most extraordinary thinkers and doers. This is the space for transformation gurus, bold hearts, black sheep, and unsung visionaries. We go beyond digitized tips and AI-smooth talk. Here, you get real, time-tested, experience-driven wisdom—the kind that blends logic and love, art and science, hindsight and foresight. For me, this show marks career transition #18. Across 17 transitions, I’ve been mentored by global changemakers who helped me emerge stronger and freer. Now, I’m passing that power forward—through raw, unfiltered conversations with extraordinary people across cultures, industries, and identities. If you’re a growth progressive, a black horse, a visionary underdog, or someone boldly rewriting the rules—you’re already one of us. Because you are the Chief Change Officer. Our mission? To help you become wiser in action, clearer in thought, and more ambitious in motion—so you can outgrow yourself and unlock outcomes beyond imagination or calculation. A better you is already unfolding. 130,000+ followers are outgrowing. Join them on LinkedIn, Apple, Spotify, and YouTube @chiefchangeofficer.