Hi, I’m Theo Hill, founder of Uphill Benefit Group. My mission is simple: to help seniors and their families navigate Medicare with confidence, clarity, and care.

With years of experience in Medicare, health insurance, and senior advocacy, I understand that choosing the right plan isn’t just about numbers—it’s about people, lifestyles, and peace of mind.

That’s why I take the time to listen, educate, and guide every client as if they were my own family.

At Uphill Benefit Group, I’ve built a service that goes beyond enrollment. I focus on trust, education, and long-term relationships, ensuring that my clients always feel supported—whether it’s during Annual Enrollment Period or anytime questions arise throughout the year.

Outside of Medicare, I’m also a healthcare consultant, a community advocate, and someone passionate about helping people live healthier, fuller lives.

My background in risk management and quality control has shaped my approach: structured, detail-oriented, and committed to getting it right the first time.

When you work with me, you’re not just getting an agent—you’re getting a partner dedicated to helping you make the best decisions for your health and your future.

Uphill Benefit Group isn’t just a name—it’s a promise. I believe no matter where you are in life, there’s always a way forward.

My goal is to make sure that path is clear, accessible, and tailored to you.