Chief Change Officer Podcast Summary – Episode #378: Alison Stewart: The LinkedIn DM That Launched a Startup (Part One)
Release Date: May 18, 2025
Introduction
In episode #378 of the Chief Change Officer podcast, host Vince Chen engages in a compelling conversation with Alison Stewart, a seasoned professional who transitioned from over a decade in the finance and insurance sectors to the dynamic realm of startups. This episode delves into Alison's personal and professional transformations, exploring her motivations, strategic decisions, and a pivotal LinkedIn connection that catalyzed her latest venture.
Alison Stewart's Career Journey
Alison kicks off her story by outlining her extensive background in the insurance industry. Beginning her career in Washington D.C. as an insurance broker, she soon realized her passion for change and operational roles over rigid, vertical career paths. Her pursuit of diverse experiences led her back to the financial sector after business school, where she thrived in an internal consulting role at a Fortune 100 company. However, after her business unit was sold, Alison sensed that her impact within large corporations was waning, prompting her to seek more meaningful and rapid growth opportunities.
Alison Stewart [03:41]: "I really enjoy change. I don't want to be in a vertical in my career. I didn't want to grow up in a specific lane."
Eventually, Alison found her calling at Overalls, a startup focused on redefining employee benefits and experiences. Over the past three years, she has been instrumental in growing the company, embracing the inherent risks and rewards of the startup environment.
Embracing Change: Personal Philosophy
Vince probes deeper into Alison's affinity for change, especially considering her childhood experiences. Alison reflects on her frequent relocations between ages 5 and 14, moving five times within the United States. These early moves required her to constantly adapt, forging new friendships and integrating into diverse communities. This adaptability became a cornerstone of her approach to professional transitions.
Alison Stewart [07:07]: "I always like to think that it's a new beginning. What good am I going to make out of this? How do I take control of the situation?"
Alison emphasizes that her positive outlook on change stems from a mindset shift—viewing change as an opportunity rather than a disruption. This perspective empowers her to navigate both voluntary and involuntary changes with resilience and optimism.
Making the Big Change During the Pandemic
The conversation shifts to the catalyst for Alison's latest career move—the COVID-19 pandemic. Like many, Alison found the unprecedented global crisis to be a profound moment of introspection. Working at Lincoln Financial, she observed patterns of leadership instability and diminishing personal fulfillment despite the company's robust structure and benefits.
Alison Stewart [11:00]: "During the health crisis, it was like a wake-up call. I haven't really been fully fulfilled in this role for some time, and now's the time to make that change."
The pandemic-induced uncertainty propelled Alison to reassess her career trajectory. With the support of her husband's stable job, she felt secure enough to embark on a new venture without compromising her family's financial stability. Rather than blindly searching for job postings, Alison undertook a deliberate self-reflection process to identify what truly mattered to her in her next role.
Alison Stewart [14:30]: "I wanted to step back and say, all right, what do I really like about the job that I'm doing right now? What am I good at?"
This strategic approach ensured that her transition was both thoughtful and aligned with her personal and professional aspirations, mitigating risks often associated with such significant career shifts.
Using LinkedIn for Career Transition
Vince then transitions the discussion to Alison's utilization of LinkedIn in her job search, highlighting her successful connection with Overalls' co-founder through the platform—a genuine LinkedIn success story amid prevalent skepticism about online networking.
Alison elaborates on her proactive engagement with LinkedIn, not merely as a job-hunting tool but as a means to extract valuable insights and connect with like-minded professionals. She meticulously analyzed job descriptions to identify appealing elements and leveraged her MBA alumni network for guidance.
Alison Stewart [19:02]: "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."
Her discovery of Overalls began with a company announcement she received via email. Intrigued by their mission, she conducted further research on LinkedIn and shared her enthusiasm with her networking group, who unanimously recognized the alignment with her skills and passions. This strategic and authentic approach facilitated a meaningful connection that would soon evolve into her role at Overalls.
Conclusion
Episode #378 offers an insightful exploration of Alison Stewart's deliberate and reflective approach to career transformation. By intertwining personal experiences with professional strategy, Alison exemplifies how embracing change with intention can lead to fulfilling and impactful career paths. Part One sets the stage for an in-depth look at her current venture, Overalls, promising listeners valuable lessons in navigating career transitions thoughtfully.
Stay tuned for Part Two, where Vince and Alison will delve into Overalls’ innovative approach to employee benefits, exploring its potential impact on workplace loyalty and employee well-being.
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