Courtney Wilson
Courtney Wilson is a Health Insurance Advocate and the Founder of Sincerra, a mission-driven consultancy dedicated to helping individuals, professionals, and 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 business owners toward cost-effective benefits solutions that support and protect their teams. With a background spanning insurance, sales, finance, 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, Fisher-Price/Mattel, M&T Bank and YMCA Buffalo Niagara and she holds 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.
• Licensed Insurance Agent
• Argosy University Bachelors Psychology
• Crisis Line Worker
Crisis Line Worker
Family Help Center
What do you attribute your success to?
Honestly, my success comes from a genuine desire to help people. I don’t have a more complicated explanation than that. When I center myself in the intention of simply making things better for others, everything else tends to fall into place. I truly believe that when you align your mindset with service, clarity, and purpose, the results follow naturally.
What’s the best career advice you’ve ever received?
The best career advice I've ever received was to bet on myself. To figure out what I'm most passionate about and align what I do with those passions and to authentically be myself. I took that advice and never looked back.
What advice would you give to young women entering your industry?
I know I've said this before but best advice I can give is to figure out your why and align yourself with who you are as a person. Why do you want to be in this industry? What objective do you hope to accomplish? People will definitely try to fit you into the mold of how they believe you will earn success, know what your core values are as a person and lead from there. Being an ally to those you serve in this industry will always be better than making a sale.
What are the biggest challenges or opportunities in your field right now?
Biggest challenges are the endless scams and the incredibly overwhelming amount of misinformation out there regarding health insurance. People have their guards up, and rightfully so. Makes connecting with people, and building a trusting partnership all the more difficult for those who are trying to make a positive impact. Add in the ever changing healthcare system in general and the plethora of options to navigate out there it's really now wonder people experience so many challenges finding and understanding their best options.
What values are most important to you in your work and personal life?
Rather it's with a client, a prospect or within my personal relationships, honest, clear and transparent communication is a must. All successful relationships/partnerships are built upon a foundation of trust, and for me you only get there by always being authentic, clear and transparent in both your thoughts and actions.