When your clients reach 65, retire, or lose employer coverage, Medicare becomes part of every planning conversation. You don’t need to become a Medicare expert to help them through it. I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, and my Black-owned agency, Chaperone Health Insurance Plus, is based in Fort Lauderdale. I work with financial advisors, CPAs, attorneys, and medical offices whose clients need personal, plain-language help with Medicare and other health coverage.
Your clients work with me directly, from the first conversation through enrollment and every annual review after that. I check their doctors, prescriptions, and full-year costs before recommending anything, and I stay their agent long after they enroll. My help comes at no extra cost to your clients, and there’s no obligation to enroll.
Medicare decisions often land at the same time as retirement income planning, Social Security timing, and tax planning, and a mistake can be costly. Missing an enrollment window can mean a gap in coverage or a late-enrollment penalty that may last as long as your client has Medicare. I handle the Medicare side carefully, so you can stay focused on the broader relationship.
For each client, I check their doctors and hospitals against each plan’s network, run every prescription through each plan’s drug list, and give them a full-year cost estimate, not just the premium. Their quote and plan review are free, with no obligation to enroll. Book a free plan review for a client, or reach out to talk about working together first.
Hear how I help you choose a plan with confidence.
When you’re choosing someone to trust with your clients, here’s what you can expect from me.
Your Clients Work With Me Directly: I handle every client personally, with no hand-offs to an assistant or call center. When your client calls, they reach me, and I know their situation.
Independent, Not Tied to One Company: I’m an independent agent, so I compare plans from multiple carriers side by side. I don’t offer every plan in every area, and I’m always clear with clients about which plans are available through me.
More Than Medicare: Many of your clients have needs beyond Medicare. I also help with ACA Marketplace coverage for early retirees and spouses under 65, small-group health plans for business owners with 50 or fewer employees, and dental, vision, life, and supplemental insurance. One trusted agent can cover the whole household.
Experienced and Recognized: I’ve spent 14 years in insurance, the last 8 focused on Medicare, and I’ve helped more than 1,800 clients. HealthMarkets has ranked me among its top 100 agents nationwide every year from 2022 through 2026.
Careful With Personal Information: My background in Information Technology shapes how I handle the sensitive details clients share during enrollment, such as Social Security numbers and medical history.
A Local, Black-Owned Agency: Chaperone Health Insurance Plus is my own Black-owned business, rooted in South Florida. Many professionals and community organizations look for Black insurance agents near them to recommend, and I’m proud to be that resource.
Licensed and Verified: I’m licensed in 33 states and AHIP certified for the 2027 plan year. You can verify my license (Florida License #W323530, NPN #17946070) anytime through your state’s insurance department.
You can read all 25 reasons we should work together on my Why Choose Me page.
Medicare rules protect beneficiaries from unwanted sales calls, so I can’t call your client based on a referral alone. The client needs to reach out to me, or ask me to contact them. That keeps the process simple:
Share my information: Give your client my phone number, (954) 410-3710, my email, contact@chaperonehealthinsuranceplus.com, or a link to book a free plan review. You can also send a short email introduction with your client copied, so they can reply to me directly.
We review the details: I talk with your client about their doctors, prescriptions, budget, and timing, then compare their options and explain each one in plain language. I never pressure anyone to enroll.
Ongoing support: After enrollment, I review their coverage every year and help with claims and billing questions in between. With your client’s written permission, I’m glad to keep you updated on their coverage decisions.
Early introductions help most when Medicare timing overlaps with other financial decisions. Consider bringing me in when a client is:
Turning 65: especially if they’re still working, have an HSA, or have a spouse who isn’t yet eligible for Medicare. I help people turning 65 or retiring plan their enrollment around their birthday, retirement date, and employer coverage.
Retiring or leaving employer coverage: including clients considering COBRA, which doesn’t protect them from Part B late-enrollment penalties the way active employer coverage does.
Facing higher Medicare premiums because of income: Medicare adds an income-related amount to Part B and Part D premiums for higher-income beneficiaries. I explain how it shows up in their coverage costs, while you and their CPA handle the tax planning side. See my guide to IRMAA and Medicare planning.
Moving to Florida or another state: plan availability, networks, and drug coverage can change with a new address.
Helping a parent: adult children often need help understanding a parent’s Medicare options, and I’m glad to include family in the conversation with the client’s permission.
Financial Advisors: a dedicated Medicare resource for clients approaching retirement or changing coverage, so Medicare costs fit into their income plan.
CPAs: support for clients whose Medicare costs are affected by income, Roth conversions, or the sale of a business or home. I don’t give tax advice, so I work alongside you on the coverage side.
Estate Planning and Elder Law Attorneys: help for clients whose Medicare and Medicaid questions intersect with long-term care and estate planning, including people who may qualify for both programs.
Medical Practices: a trusted contact for patients who ask your staff for help understanding their Medicare options and enrollment.
Business Owners and HR Contacts: help for employees aging into Medicare and for small businesses comparing group health plans.
Working with me can be a good fit if your clients want one person to compare their options, explain the trade-offs clearly, and stay available after they enroll. It’s especially helpful for clients who take several prescriptions, want to keep a particular doctor, are leaving employer coverage, or have a household with both Medicare and under-65 coverage needs. My help comes at no extra cost to your clients, and there’s no obligation to enroll.
I meet clients by phone, on Zoom, at my office in Fort Lauderdale, or at their home anywhere in Broward, Miami-Dade, and Palm Beach counties. Clients in the other 32 states where I’m licensed can work with me by phone or Zoom.
Most households need more than one kind of coverage, and what you need changes as life does. Keep reading for the details on this page, or see all the coverage I help with and my guides to each type of insurance:
Do You Charge My Clients or Me Anything?
No. My help comes at no extra cost to your clients, and plan reviews and quotes are free with no obligation to enroll. Insurers pay my commission, and premiums are generally the same whether a client enrolls through me or directly with the carrier.
Can You Call My Client Directly After I Refer Them?
Medicare rules don’t allow agents to make unsolicited calls based on a referral, so your client should reach out to me first, or ask me to contact them. The easiest way is to share my number or booking link, or send an email introduction with your client copied.
Will You Keep Me Informed About My Client’s Coverage?
With your client’s written permission, yes. Otherwise, I keep their health and personal information private.
What Does a Medicare Consultant Do That I Can’t?
As a licensed, independent Medicare broker, I can compare specific plans, check each client’s doctors and prescriptions against those plans, and complete the enrollment. I also review their coverage every year and help with claims and billing questions in between.
Are You a Black-Owned Insurance Agency?
Yes. Chaperone Health Insurance Plus is my own Black-owned agency, based in Fort Lauderdale. I’m an independent licensed agent with HealthMarkets Insurance Agency, which gives my clients access to plans from multiple carriers.
Do You Help With More Than Medicare?
Yes. I also help with ACA Marketplace and off-Marketplace health plans for people under 65, small-group plans for businesses with 50 or fewer employees, Medicare and Medicaid dual eligibility, Extra Help, and dental, vision, life, and supplemental insurance.
Do You Work With Clients Outside Florida?
Yes. I’m licensed in 33 states. Clients outside South Florida work with me by phone or Zoom.
Introduce a client, or pick a time to talk with me about working together. Clients can book a free 15-minute call by phone or video, and my help never costs them anything extra.
Call or text: (954) 410-3710
Email: contact@chaperonehealthinsuranceplus.com
Office: 6360 NW 5th Way Ste 101, Fort Lauderdale, FL 33309
Meet by: phone, video, at my office, or at home in Broward, Miami-Dade and Palm Beach.
Five steps, no pressure, and I stay with you after you enroll.
By phone, Zoom or face to face. Your health, your budget, your doctors.
Doctors, hospitals, prescriptions and pharmacy, checked against each plan.
A full-year estimate for each option, explained in plain language.
No pressure. If you choose a plan, I handle the application with you.
Plans and networks change. I check yours each year and help with claims in between.