Season 10 Ep. 1 -Brandy Thompson- CEO of benefitbay episode artwork

EPISODE · Apr 16, 2026 · 32 MIN

Season 10 Ep. 1 -Brandy Thompson- CEO of benefitbay

from rEvolutionary Woman · host Tes Silverman

What does it really look like to lead a company, raise a family, and build something meaningful at the same time? In this episode of Revolutionary Women, Tes Silverman sits down with Brandy Thompson, CEO and Founder of BenefitBay, for an honest conversation about leadership, motherhood, and taking a path that doesn’t always look traditional. Brandy shares how she moved from finance and HR into the CEO role, and how her experience as a mother of six shaped the way she leads. She talks about building a company rooted in empathy, creating space for real-life responsibilities, and why understanding people matters just as much as performance in today’s workplace. You’ll also hear how BenefitBay is helping reshape employee health benefits through ICHRA (Individual Coverage Health Reimbursement Arrangements), giving both employers and employees more flexibility and choice. This episode is for women in leadership, working moms, entrepreneurs, and anyone figuring out their next step while juggling real life. One of the most meaningful takeaways from this conversation: “You don't have to have followed the yellow brick road to get to where you are.” Brandy Thompson is the CEO and Founder of benefitbay®, a Kansas City based health benefits technology company focused on modernizing how employers deliver coverage through ICHRAs. She is a mother of six and has built her company with an intentionally people-first approach, including hiring frontline team members with backgrounds in education and healthcare to deliver a more empathetic enrollment experience. Brandy’s leadership story is rooted in values-based decision-making, building at a sustainable pace, and designing a workplace that supports real life responsibilities, especially for working parents. To learn more about Brandy Thompson: LinkedIn: https://www.linkedin.com/in/brandy-thompson-24389536/ To learn more about benefitbay: https://www.linkedin.com/company/benefitbay

What does it really look like to lead a company, raise a family, and build something meaningful at the same time? In this episode of Revolutionary Women, Tes Silverman sits down with Brandy Thompson, CEO and Founder of BenefitBay, for an honest conversation about leadership, motherhood, and taking a path that doesn’t always look traditional. Brandy shares how she moved from finance and HR into the CEO role, and how her experience as a mother of six shaped the way she leads. She talks about building a company rooted in empathy, creating space for real-life responsibilities, and why understanding people matters just as much as performance in today’s workplace. You’ll also hear how BenefitBay is helping reshape employee health benefits through ICHRA (Individual Coverage Health Reimbursement Arrangements), giving both employers and employees more flexibility and choice. This episode is for women in leadership, working moms, entrepreneurs, and anyone figuring out their next step while juggling real life. One of the most meaningful takeaways from this conversation: “You don't have to have followed the yellow brick road to get to where you are.” Brandy Thompson is the CEO and Founder of benefitbay®, a Kansas City based health benefits technology company focused on modernizing how employers deliver coverage through ICHRAs. She is a mother of six and has built her company with an intentionally people-first approach, including hiring frontline team members with backgrounds in education and healthcare to deliver a more empathetic enrollment experience. Brandy’s leadership story is rooted in values-based decision-making, building at a sustainable pace, and designing a workplace that supports real life responsibilities, especially for working parents. To learn more about Brandy Thompson: LinkedIn: https://www.linkedin.com/in/brandy-thompson-24389536/ To learn more about benefitbay: https://www.linkedin.com/company/benefitbay

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Season 10 Ep. 1 -Brandy Thompson- CEO of benefitbay

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What does it really look like to lead a company, raise a family, and build something meaningful at the same time? In this episode of Revolutionary Women, Tes Silverman sits down with Brandy Thompson, CEO and Founder of BenefitBay, for an honest...

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