Hi, I’m Roxroy Ashley

I’ve spent 14 years in the insurance industry, the last 8 of them focused on Medicare. Before that, I built a background in business and technology, with a Master’s in Business and a BA in Information Technology – which is a big part of why I like turning complicated plan details into something clear and simple.

Today I’m an independent licensed agent with HealthMarkets Insurance Agency, Inc., operating as Chaperone Health Insurance Plus. I help individuals, families, and business owners find coverage that fits their health, their budget, and their life, with personal guidance every step of the way.

How I Got Here

I didn’t start out in insurance planning to specialize in Medicare, but over time I found that this is where I could make the biggest difference for people. Turning 65, retiring, or losing employer coverage are moments when a small mistake can be costly – a missed deadline, a wrong plan choice, a doctor who turns out to be out of network. I’ve spent years helping people get through those moments without the stress, and it’s become the work I care most about.

Why Work With Me

I confirm your providers, medications, and pharmacy are covered before recommending any plan. I compare plans from the major carriers as an independent agent, and my help doesn’t add to your premium. I look beyond the monthly premium to your copays, drug costs, and out-of-pocket maximum, so you know your true yearly cost. And there’s never any pressure or obligation – I’ll walk you through your options and let you decide what’s right for you.

I’m proud that more than 8 out of 10 of my clients stay with me year after year, based on my own client records. To me, that’s the real measure of whether I did my job.

These are just a few of the reasons clients choose to work with me. You can see all 25 reasons on my Why Choose Me page.

Coverage for Every Stage of Life

I work with clients on Medicare Advantage, Medicare Supplement (Medigap), and Part D prescription plans, as well as ACA Marketplace and off-Marketplace health insurance for anyone under 65. I also help small business owners and self-employed individuals with group and individual coverage, assist people who may qualify for Medicare and Medicaid dual eligibility, Special Needs Plans, or Extra Help, and round out coverage with dental, vision, life, and supplemental insurance. Whatever stage of life you’re in, you can come to one agent instead of juggling several.

Licensed and Recognized

I’m licensed in 33 states (Florida License #W323530, NPN #17946070), AHIP certified for the current plan year, and registered with the federal Health Insurance Marketplace. I’ve helped more than 1,800 clients and have been recognized among the Top 100 HealthMarkets agents nationwide.

Personal Service, Year-Round

You’ll work with me directly – in person, by phone, or on Zoom – long after you enroll. I meet clients at my Fort Lauderdale office, or at home across Broward, Miami-Dade, and Palm Beach counties. My support doesn’t end at enrollment; I review your coverage every year and help with claims and billing issues whenever they come up.

Let’s Find the Right Plan Together

Tell me a little about what you need, and I’ll get back to you personally within 24 to 48 hours. There’s no cost and no obligation to enroll.

Phone: 954-410-3710
Email: contact@chaperonehealthinsuranceplus.com
Office: 6360 NW 5th Way Ste 101, Fort Lauderdale, FL 33309