Derek Raynes

I am an attorney, healthcare executive, and independent business owner based in Vermont. I lead Raynes Healthcare Resources and own Alpine Options, a ski shop in Warren, Vermont. My career has taken me through law, healthcare, and retail, an unlikely combination that has shaped how I think about organizations, people, and business.

I am most interested in work that rewards curiosity, judgment, and a willingness to look closely. I help my healthcare clients make sense of complicated business situations so they can move forward with purpose and clarity. At the ski shop, I am steeped in practical decision-making in a competitive retail industry, and work physically in ways I have not experienced in decades. Shifting between strategy, judgment, and the demands of running a real business keeps my mind elastic.

Through Raynes Healthcare Resources, I consult, write, and teach about the business of healthcare. Through Mansfield Primary Care Support, I work directly with independent primary care practices.

My background includes more than ten years practicing law, along with managed care and contracting leadership roles at Shands at the University of Florida and the University of Vermont Medical Center. At OneCare, I spent five years helping administer the All-Payer Model for the State of Vermont, including operating a fixed payment program for independent primary care practices (CPR), a quality performance and incentive program (PHM), hospital fixed payments, and total cost of care risk programs with Medicare and Medicaid.

My experience offers clinicians a view they rarely have from inside their own walls: how payment reform is designed, negotiated, financed, and administered. I understand the healthcare business problems they face and the importance of remaining independent, especially in Vermont, where being fiercely independent is part of who we are.

I bought Alpine Options because I wanted to own something tangible in an industry I genuinely enjoy. Running a ski shop has taught me retail from the floor up. I buy inventory, work with vendors, manage staff, serve customers, and make decisions with consequences that show up quickly and plainly.

The shop has also become a creative outlet. I shape its voice, marketing, and customer experience, test ideas in real time, and learn from what works and what does not. It is a different kind of work from healthcare consulting, and that difference is exactly what makes it valuable to me.

If you would like to talk about a project, compare notes, or just say hello, I’d be glad to hear from you.