Chief Change Officer - Episode #257: Alison Stewart: The LinkedIn Message That Changed Everything — Part One

Host: Vince Chan
Guest: Alison Stewart
Release Date: March 26, 2025

Introduction

In Episode #257 of the Chief Change Officer podcast, host Vince Chan engages in a profound conversation with Alison Stewart, a seasoned professional who transitioned from a decade-long career in finance and insurance to the dynamic world of new ventures. This episode, the first part of a two-part series, delves into Alison's personal transformations, motivations for change, strategic steps she undertook, and her pivotal LinkedIn experience that connected her with her current co-founder.

Alison Stewart's Career Journey and Evolution

Alison Stewart provides an insightful overview of her professional journey, highlighting her initial focus on the insurance industry and her evolving interests in operational roles that offered broader exposure beyond a single vertical.

Alison Stewart [05:37]:
"I spend about five years with an insurance broker company, then went back to business school to figure out my next step. I realized I enjoy change and didn’t want to grow up in a specific lane."

Alison's tenure at a Fortune 100 company involved an internal consulting role that allowed her to rotate across different business units, further fueling her passion for continuous learning and adaptability.

Alison Stewart [06:20]:
"Being moved around in an internal consulting role really fed my desire to keep learning and try different things."

Despite the stability and benefits offered by large corporations, Alison felt a growing need for greater impact and decided to embrace the uncertainties of the startup ecosystem, leading her to co-found Overalls—a venture focused on redefining employee benefits and experiences.

Motivations Behind Career Change

The catalyst for Alison's significant career shift was not just a desire for personal growth but also a deeper yearning for meaningful impact. She articulated her discontent with the stagnation she felt within large organizations and her aspiration to engage in something more innovative and risk-oriented.

Alison Stewart [07:58]:
"I felt like the impact I was having wasn't what I wanted it to be. I wanted to do something a little bit more risky, something that could help me learn and grow faster."

This introspection was further intensified by her experiences during the COVID-19 pandemic, which prompted her to reassess her professional fulfillment and life goals.

Impact of the COVID-19 Crisis on Alison's Decision

The unprecedented global health crisis served as a pivotal moment for Alison, compelling her to confront her professional satisfaction and future aspirations. The restrictions and uncertainties of the pandemic underscored the transient nature of stability and prompted her to seek a more fulfilling and autonomous career path.

Alison Stewart [12:56]:
"The crisis and that change just was a wake-up call. It was like, 'You haven't really been fully fulfilled in this role for some time and now's the time to make that change.'"

Alison meticulously evaluated her career within Lincoln Financial, recognizing patterns of regressive steps masked as progress under new leadership. This realization, coupled with her personal circumstances—being pregnant with her second child—added layers of complexity to her decision-making process.

Alison Stewart [16:26]:
"I had to make that time to do that evaluation and kind of force it for me."

Her approach was both deliberate and strategic, ensuring that the transition was financially manageable and aligned with her family's needs, thereby mitigating potential risks associated with such a significant career move.

The LinkedIn Success Story

A pivotal moment in Alison's transition story revolves around her effective use of LinkedIn to connect with her future co-founder at Overalls. Contrary to common skepticism surrounding job postings and networking on the platform, Alison's experience was authentic and fruitful.

Alison Stewart [23:04]:
"I saw our CEO on LinkedIn and happened to have my meeting that day with my networking group. They almost stopped me and said, 'Alison, it's very clear to me this opportunity is what you're looking for.'"

Her proactive engagement with LinkedIn involved not just passive job searching but active analysis of job descriptions, leveraging her MBA alumni network, and synthesizing insights from conversations with peers. This multifaceted approach enabled her to identify and seize a genuine opportunity that aligned with her skills and aspirations.

Alison Stewart [25:24]:
"I was scanning LinkedIn jobs, pulling elements from different job descriptions that were intriguing to me, and using my networks to talk about these types of job changes."

This successful connection underscores the platform's potential when used thoughtfully and strategically, highlighting the importance of genuine networking over superficial interactions.

Conclusion

In this engaging episode, Alison Stewart's narrative serves as an inspiring blueprint for professionals contemplating significant career transitions. Her journey encapsulates the essence of embracing change proactively, leveraging available resources effectively, and maintaining a strategic and reflective approach to career development.

Stay tuned for Part Two, where Vince and Alison will delve deeper into Alison's current venture, Overalls, and explore its innovative approach to employee benefits and workplace loyalty.

Notable Quotes:

• Alison Stewart [05:37]:
  "I didn't want to grow up in a specific lane. I found I really gravitated towards operational roles where you have your hands in more things."

• Alison Stewart [09:02]:
  "Growing up, I moved five times between the ages of 5 and 14. Navigating new communities taught me to embrace change."

• Alison Stewart [12:56]:
  "The crisis was a wake-up call. I realized I wasn't fully fulfilled and needed to make a change."

• Alison Stewart [25:24]:
  "I was scanning LinkedIn jobs and pulling elements from different job descriptions that were intriguing to me."

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