Brandy Thompson
CEO and Founder
Kansas City, Missouri
My Role
As the Founder and CEO of benefitbay®, I lead the strategic vision and overall growth of a platform that is redefining how employers deliver health benefits through Individual Coverage Health Reimbursement Arrangements (ICHRA). My role involves building and managing key partnerships with national agencies and insurance carriers, driving product innovation that makes healthcare more efficient and affordable, and championing a human-centered approach to benefits enrollment. At benefitbay®, we’ve made a deliberate choice to hire former teachers and nurses—individuals who bring empathy, patience, and real expertise—instead of relying on temp staffing. I also focus on educating brokers and employers on how to adopt ICHRA in a way that supports both cost containment and employee choice. Externally, I serve as the voice of the company in media, on stage, and in policy conversations, advocating for a modern, inclusive health benefits system. Internally, I work to maintain a values-driven culture—one that earned us a spot on Inc.’s 2025 Best Workplaces list. At the heart of everything I do is a belief that healthcare should be personal, scalable, and built with care.
What I love most about my role
What I love most about my role is the opportunity to create meaningful change in a system that has historically left too many people behind. At benefitbay®, we’re not just offering a new way to deliver health benefits, we’re empowering employers, brokers, and everyday families with choice, clarity, and compassion. I get to lead a team that believes in the human side of healthcare, whether that’s through hiring former teachers and nurses to guide employees through open enrollment or building technology that reduces inefficiencies and cost. Seeing our work directly improve someone’s access to care, simplify a complex decision, or support a working parent trying to navigate benefits—it’s incredibly fulfilling. Every day, I get to build something that’s values-led, scalable, and deeply personal. That’s a rare and powerful combination.
How I define success
I define success as building something that makes life tangibly better for the people it touches, whether that’s employees choosing the right health plan with confidence, brokers feeling empowered by better tools, or my own team feeling fulfilled in their work. Success isn’t just about hitting metrics or scaling fast; it’s about creating lasting impact. For me, it means staying aligned with our mission, maintaining integrity in how we operate, and knowing that we’re solving real problems with heart and intention. If we’re improving access to care, elevating the role of women and caregivers in the workforce, and leading with empathy while still growing as a business, that’s success.
The best piece of business advice I ever received was
The best piece of business advice I’ve ever received is: “Build for the people doing the work, not just the people making the decisions.”
It’s a simple reminder that sustainable success comes from understanding and solving real pain points for the end users. Whether that’s the HR manager juggling open enrollment, the teacher trying to navigate benefits for her family, or the broker needing a faster, more reliable system. When you lead with empathy and design with intention, the business case follows.
What would I tell my younger self
I’d tell my younger self: “Don’t wait for permission, lead with conviction.”
There were moments early in my career when I held back because I didn’t feel “ready enough” or thought someone else must have more authority. But what I’ve learned, especially as a founder and a mom of six, is that clarity and courage don’t always arrive together. You grow into leadership by stepping into it. I’d remind her that her perspective matters, her instincts are strong, and that the systems she wants to change are absolutely worth challenging.
What 2B Bolder mean to me
To me, 2B Bolder means giving yourself permission to dream bigger, speak louder, and take up space—especially in rooms where you may have once felt like an outsider.
As a female founder in a male-dominated industry, and as a mother of six building a company from the ground up, being bolder isn’t just about ambition, it’s about impact. It means using your voice to advocate for others, redesigning systems that don’t work, and making choices that reflect your values, not just your résumé. It’s about showing up fully—as a leader, as a woman, and as a human, and refusing to shrink yourself to make others more comfortable.
Years of Experience
15 years of experience in the HR, finance, and employee benefits space.
I recommend you focus on developing these 3 skills to succeed in a role like mine
Strategic Leadership in Health Benefits – Deep expertise in designing and scaling innovative health benefit models like ICHRA, with a focus on personalization and cost-efficiency.
Human-Centered Operations – Known for building mission-driven teams by hiring educators, nurses, and service-minded professionals to improve user experience and enrollment support.
Broker and Carrier Channel Development – Proven ability to grow partnerships with top national broker agencies (e.g., Gallagher, Lockton, HUB) and lead industry-first carrier integrations to streamline processes and reduce costs.