#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.