About Us
Meet Your Medicare Team in Greensboro, NC
Formerly known as The Insurance Coach
Rob Leonard
Medicare Advisor, Former Coach, Still Asking Questions
Rob Leonard has been in insurance for 26 years. For the last 21 of them, he's focused on one thing: Medicare. Not annuities. Not life insurance packages. Not financial planning. Medicare — because it's complicated enough to deserve that kind of focus, and because the people navigating it deserve someone who actually knows it cold.
Before insurance, Rob coached lacrosse. He'll tell you that's where the philosophy came from. A coach doesn't play the game for you — a coach helps you understand the situation, shows you the options, and lets you make the call. That's how he runs every consultation. He asks more questions than most advisors. He listens before he recommends. He doesn't push a product — he finds a fit.
That approach built a practice that runs almost entirely on referrals. When your clients come back every year, and most new clients come through referrals, you're doing something right. Rob's not going to tell you he's the best Medicare advisor in Greensboro — but his clients will.
Marian Ragsdale
If you've called the office, you've probably already talked to Marian. She handles the day-to-day operations, keeps client communications organized, and makes sure nothing falls through the cracks. She knows most clients by name before they walk in the door.
In an industry where you can spend 45 minutes on hold with an insurance carrier and never reach a real person, Marian is the person who answers. That matters more than most people realize until they actually need help.
The Person Who Actually Keeps This Place Running
Ryan Gehsmann
Investment Advisor Representative
Ryan began his career in the Financial Services Industry right out of college in 2015. Ryan’s passion for helping others through wealth management and financial planning strategies led him to become an Accredited Asset Management Specialist (AAMS) through the College for Financial Planning in 2016. After five years in the industry Ryan became licensed to prepare tax returns in 2021, then continued on to earn the Enrolled Agent (EA) designation in 2024. Through this acquired knowledge and experience in a range of financial topics, Ryan is able to add more value to his investment clients.
Ryan’s objective is to help clients plan and save for their future in the most effective way possible. He begins this process by discussing his client’s long and short-term goals and objectives, as well as their previous investment and financial experience. Through these comprehensive steps, Ryan can then form customized plans based upon the personal goals and values most important to his clients.
EDUCATION
Bachelor of Science – Business Administration, University of South Carolina, 2015
PERSONAL
Ryan resides in Greensboro, North Carolina and is an active member in the community. In addition to his career in the Financial Services Industry, Ryan is the Head of Adult Programming with NC Fusion. His role with NC Fusion highlights his love for community, where he hosts and participates in service activities and sporting events such as the Greensboro Lacrosse Classic tournament. He has been involved in youth development projects since 2008 including lawn care, academic mentorship programs, and coaching youth recreational sports. In his free time Ryan enjoys spending time with his wife, Kelsey, their son, Caison, and their daughter, Riley.
🐾 Myrtle
Our Director of First Impressions
Myrtle is the newest addition to the Leonard family, named in honor of my grandmother, Myrtle, whose kindness and spirit continue to inspire the way we serve our clients.
When we rebranded from The Insurance Coach to Rob Leonard & Associates, Insurance Advisors, we knew Myrtle had to be part of the journey. She brings joy, warmth, and a wagging tail to the office — and she takes her role as company mascot very seriously.
If you visit our office, there’s a good chance you’ll meet her. Myrtle often comes to work with me and loves greeting clients, making her the perfect “Director of First Impressions.”
More About Myrtle
We chose Myrtle as our mascot because she always fetches exactly what she needs — and just like Myrtle, we’re committed to fetching the right Medicare plan for you. When she was a puppy, Myrtle starred in a short video that unexpectedly went viral, earning more than
188,000 views. It’s a fun glimpse into her personality and the joy she brings to everyone around her.
Myrtle’s Family on TV
In Christmas 2025, Chevrolet released a heartwarming holiday commercial featuring four dogs of different ages — including Myrtle’s dad and her pup siblings. It’s a touching, beautifully filmed piece that we love sharing with our clients.
Your Relationship Doesn't End When Someone Retires
Most advisors don't think about what happens to their clients when they retire. We do. A succession plan is already in place — so when the time comes, you won't be starting over with someone who doesn't know your history, your doctors, or what you've been through with your coverage. Your relationship with this office continues. That's not an accident. It's something we built on purpose.
21 Years of Medicare Experience
Independent — All Major Carriers
Local Greensboro Office Since 2003
Referral-Driven Practice
What insurance do I need in addition to Medicare in Greensboro, NC?
It depends on your health, your budget, and what your Medicare plan already covers. Most people benefit from at least dental and vision coverage, since Original Medicare excludes both. Long-term care and hospital indemnity are worth reviewing depending on your financial situation and family history. We walk through all of it in a free consultation — no pressure, just a clear picture.
Does Medicare Advantage include dental and vision coverage?
Some Medicare Advantage plans include limited dental and vision benefits, but the coverage is often more restricted than people expect — lower annual maximums, limited networks, or exclusions for major dental work. A standalone dental or vision plan can fill what your Advantage plan leaves behind.
How much does supplemental coverage cost for seniors in Greensboro?
Costs vary by plan type, carrier, your age, and your health history. Dental plans often start well under $50 per month. Long-term care premiums depend heavily on when you apply and how much daily benefit you select. The best way to get an honest number is a side-by-side comparison — which we provide at no charge.
Can I add supplemental coverage after I've already enrolled in Medicare?
Yes, in most cases. Dental, vision, hearing, hospital indemnity, and travel insurance are available year-round with no enrollment window restriction. Long-term care and life insurance may involve health underwriting, so earlier is generally better. We'll let you know exactly what's available based on your current situation.
Do I need a separate agent for each type of supplemental insurance?
Not with us. We handle Medicare and all the supplemental coverage categories we offer through one relationship. One advisor, one office, one phone number — regardless of how many policies you carry.
How We Work — Every Time, With Every Client
This isn't a call center. It's not an algorithm. It's three people and a dog in a real office on Pembroke Road, doing the same thing we've always done: sitting down with clients, looking at the options together, and finding what actually fits.
We file claims when something goes wrong. We stay on hold with carriers so you don't have to. We send birthday cards. We call you before Annual Enrollment opens — not after. We remember what's important to you, because we wrote it down the first time you told us.
That's the whole model. Complicated Medicare questions handled by people who know Medicare. No hand-off to a 1-800 number. No chatbot. Just us.
We work with clients in Greensboro, Winston-Salem, High Point, Burlington, and across the Piedmont Triad. Remote clients in South Carolina, Virginia, Florida, and other licensed states are served by phone or Zoom.
Common Questions About Our Team and Practice
Who is Rob Leonard and how long has he been a Medicare advisor in Greensboro, NC?
Rob Leonard is an independent Medicare broker based in Greensboro, NC, with 26 years in insurance and 21 years focused specifically on Medicare. He founded his independent practice around 2003 and has served clients across Guilford County and the Piedmont Triad ever since. His practice runs primarily on referrals from existing clients.
What makes your office different from other Medicare advisors in Greensboro?
A few things stand out. We're fully independent, which means we represent almost all of the major carriers in the region — not one company's lineup. We provide full-service support after enrollment, including claims filing and carrier follow-up. And we plan ahead: a succession arrangement with Ryan means clients have continuity no matter what. Most advisors don't talk about that. We think they should.
Do you handle Medicare for clients outside of Greensboro?
Yes. We serve clients throughout the Piedmont Triad — Winston-Salem, High Point, Burlington, Kernersville, and surrounding areas — and we're licensed in South Carolina, Virginia, Florida, Ohio, Kentucky, Maryland, and Washington state. Phone and Zoom consultations are available for clients who can't come into the office.
What happens if Rob retires or is unavailable?
We've planned for that. Ryan, a long-term colleague, is being brought into the practice to ensure continuity for existing clients. The goal is that your relationship with this office continues without interruption — you won't be starting over with someone who doesn't know your history.
Is this a real local office, or do you work remotely?
Both, depending on what works for you. Our office is at 1816 Pembroke Rd Suite 7 in Greensboro — walk-ins are welcome by appointment, and clients often come in to sit with Rob at dual monitors and compare plans side by side. We also work with clients throughout the region and across state lines by phone or Zoom.