Courtney Wilson

Courtney Wilson is a Health Insurance Advocate and the Founder of Sincerra, a mission-driven consultancy dedicated to helping individuals, professionals, and small business owners access clear, affordable, and reliable health coverage. She specializes in navigating ACA and private insurance options, developing flexible strategies for contractors and gig workers, and guiding small business owners toward cost-effective benefits solutions that support and protect their teams. With a background spanning insurance, sales, program coordination, and compliance, Courtney brings both breadth and depth to her work—along with an unwavering commitment to transparency and education.

Courtney launched Sincerra after witnessing her mother fall victim to a predatory insurance scam, an experience that revealed just how confusing and vulnerable the coverage process can be. That moment shaped her mission: to ensure people receive honest guidance, real clarity, and solutions tailored to their lives—not one-size-fits-all plans. Whether she’s leading workshops, facilitating Coverage Confidence Checks, or working one-on-one with clients, Courtney focuses on removing pressure, simplifying choices, and empowering people to feel confident in their coverage decisions.

Beyond her work with Sincerra, Courtney brings experience from roles at USHEALTH Group, Southern Glazer’s Wine & Spirits, Empire EMCO, and YMCA Buffalo Niagara. She holds a Master of Science in Child and Adolescent Development from Capella University and a Bachelor’s degree in Psychology from Argosy University. Courtney also serves as a long-time Crisis Line Worker with the Family Help Center, offering essential support and connecting families with life-changing resources. Driven by compassion and clarity, she is dedicated to reshaping the insurance experience for those who need it most.

• Capella University Capella University Master of Science
• Argosy University Sarasota Argosy University Sarasota Bachelor's degree

• Crisis Line Worker Crisis Line Worker Family Help Center