Chief Change Officer Podcast Episode #379: Alison Stewart on Building a Life Concierge Startup From Scratch—Part Two

Release Date: May 18, 2025 | Host: Vince Chan

Introduction

In Episode #379 of the Chief Change Officer podcast, host Vince Chan engages in a deep and insightful conversation with Alison Stewart. This episode, the second part of a two-part series, delves into Alison's remarkable journey from a decade-long career in the finance and insurance sectors to founding Overalls, a groundbreaking startup focused on reimagining employee benefits and experiences. Released on May 18, 2025, this episode offers listeners valuable lessons on career transitions, startup challenges, and innovative solutions to modern workplace stress.

Alison Stewart's Career Transition

From Corporate Stability to Startup Chaos

Alison Stewart shares her motivations and the strategic steps that led her to transition from a secure position in corporate America to the uncertain yet exhilarating world of startups. She recounts how, amid the COVID-19 pandemic, she identified a unique opportunity to leverage her expertise in a new domain.

"I had been pretty squarely in the insurance industry and I was interested in exploring something outside of the insurance industry... I saw Overalls announced, and wow, that is what I'm looking for."
— Alison Stewart [04:42]

Connecting Through LinkedIn

A pivotal moment in her journey was her proactive use of LinkedIn to connect with Overalls' CEO, Stanton Lee. Alison describes the deliberate and focused approach she took, contrasting it with the common practice of mass messaging.

"I took that time to be focused... I manifested it. I was focused, determined to put the time and energy in."
— Alison Stewart [08:15]

Her persistence paid off when Stanton recognized her potential and invited her to apply for the Head of Operations role—a decision that ultimately led to her current position as Chief Operating Officer three years later.

Expectations vs. Reality in the New Role

Initial Expectations

Alison anticipated a dynamic environment where she could experiment, make quick decisions, and learn rapidly. She was eager to "roll up [her] sleeves" and immerse herself in various aspects of the business.

"I was excited to take that on... Still, we're a very lean team and that's been fun."
— Alison Stewart [11:00]

Three Years On

Reflecting on her tenure, Alison confirms that her initial expectations have been met and even exceeded. Overalls has experienced significant growth and market traction, yet she continues to stay engaged at all levels of the company.

"Three years later, we've gotten bigger, we've had great market traction... I still try to make time to allow for that variety of activity."
— Alison Stewart [14:10]

Building Overalls: Mission and Impact

Mission of Overalls

Overalls aims to alleviate the "mental load" and reduce stress for employees by acting as a personal assistant for everyday life hassles. This service allows employees to focus more on their work and personal lives without being bogged down by mundane tasks.

"Overalls will take them off your plate, will be that extra set of hands for you... achieving work-life balance."
— Alison Stewart [21:44]

Connecting Employers with a Flexible Talent Pool

A unique aspect of Overalls is its network of live concierge experts, including stay-at-home parents, underemployed individuals, and retirees. These experts provide flexible, part-time assistance, enabling them to contribute their skills while maintaining their personal commitments.

"We created this win environment... our network of life experts... are working for us in a flexible part-time capacity."
— Alison Stewart [25:30]

Impact on Employers and Employees

Employers benefit from increased employee productivity and engagement, while employees experience reduced stress and enhanced work-life balance. Alison highlights how Overalls has become a valued employee benefit, with HR departments noticing significant appreciation from staff.

"Our employees are so thankful for the support you've been able to provide them."
— Alison Stewart [27:55]

Value Proposition for Employers

Employers adopting Overalls provide their teams with a valuable resource that handles personal tasks, allowing employees to remain focused and less distracted at work. This not only boosts productivity but also fosters a greater sense of loyalty and job satisfaction.

"Giving them someone to take care of it helps them stay focused, less distracted, and feel more supported at work."
— Vince Chen [26:52]

Alison emphasizes that Overalls addresses the growing mental health crisis by offering practical support, thereby contributing to a healthier and more balanced workforce.

Challenges in Transitioning to a Startup Environment

Adjusting to Diverse Responsibilities

Transitioning from a structured corporate role to a startup required Alison to embrace a wide array of tasks, from strategic decision-making to hands-on operational duties. She discusses the initial fear of inadequacy but overcame it by trusting her capabilities and prioritizing effectively.

"The biggest challenge... was do I have the skill set to do these things? Am I qualified to make some of these decisions?"
— Alison Stewart [17:44]

Building Confidence and Trusting Oneself

Alison highlights the importance of self-belief and the willingness to take on diverse roles as essential factors in successfully navigating the startup landscape.

"I had to grow and learn is to just trust myself... It worked."
— Alison Stewart [08:15]

Advice for Career Transitions

Self-Reflection and Honesty

Alison advises individuals considering a major career shift to engage in deep self-reflection. Understanding one's true motivations and aligning them with career choices is crucial for meaningful transitions.

"Doing that self-reflection and being honest with yourself on what you're looking for... talking to others about your goals really helps."
— Alison Stewart [30:27]

Accountability and Support Networks

She emphasizes the role of accountability partners—friends or mentors who can provide honest feedback and keep individuals aligned with their goals.

"We need people to hold us accountable... writing it down to hold ourselves accountable to what it is that we're looking for."
— Alison Stewart [30:27]

Embracing Growth Opportunities

Alison encourages embracing change as a continuous learning process, where each step offers new opportunities for personal and professional growth.

"Everything we tackle in life is a learning opportunity... always reinventing ourselves and refining who we are."
— Alison Stewart [31:10]

Patience and Kindness Towards Oneself

Recognizing that significant changes take time, Alison advises being patient and compassionate with oneself during the transition.

"Don't be afraid to embrace the opportunities for learning and growth... be patient with yourselves."
— Alison Stewart [31:50]

Conclusion

Alison Stewart's journey from a corporate career to founding Overalls exemplifies the essence of being a Chief Change Officer. Her experiences offer invaluable insights into navigating career transitions, building impactful startups, and fostering environments that support both employers and employees. Through deliberate actions, self-reflection, and a commitment to growth, Alison demonstrates how individuals can outgrow themselves and unlock unprecedented outcomes.

For those inspired by Alison's story, this episode serves as both a roadmap and a source of motivation to embrace change and pursue transformative opportunities.

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