Chaperone Health Insurance Plus
Small Business Insurance Agent Near You in South Florida
Running a business in South Florida means wearing a lot of hats, and sorting out health coverage for yourself and your team shouldn’t be one more job you handle alone. I’m Roxroy Ashley, an independent licensed agent with HealthMarkets, and I help business owners with 50 or fewer employees, freelancers, and the self-employed compare their coverage options side by side, explained in plain language.
Whether you’re offering group health insurance for the first time, reviewing a plan that’s coming up for renewal, or looking for your own coverage as a sole proprietor, I’ll show you the options that fit your team, your budget, and the doctors your people already use. Then I stay on as your agent long after you enroll.
I’LL EVEN CALL YOUR DOCTOR
Get a Free Quote From a Small Business Insurance Agent Who Does the Research for You
A group plan only works if it covers the doctors your team already uses, so before I recommend anything, I check:
Your team’s doctors and hospitals against each plan’s network, including HCA Florida, Memorial, and Baptist Health
Prescriptions and pharmacies against each drug list
The full-year cost for your business and your employees, not only the premium
If you’re self-employed, I do the same for your household’s plan. If a detail is unclear, I call the doctor’s office myself. Your quote is free, with no obligation to enroll. Get your free quote and I’ll do the research for you.
Hear how I help you choose a plan with confidence.
Your Small Business Health Insurance Broker From Quote to Renewal
Once you choose a plan, I handle the application with you, help your employees understand their benefits and enroll, and stay available when you add a new hire, when someone has a question about a claim or a bill, and when your plan comes up for renewal. Renewal is when rates and networks can change, so each year I review your plan and your options before you decide whether to keep it or make a change.
MORE THAN A FREE QUOTE
Why Choose Me for Small Business & Self-Employed Insurance
When you’re comparing benefits brokers, here’s what to look for, and what you can expect from me.
Coverage That Fits Your Business: I start with your headcount, your budget, and what you want the plan to do for your team, then compare options from multiple carriers for a business your size.
The Full Cost for You and Your Team: I show you the full-year cost of each plan for the business and for your employees, including deductibles and out-of-pocket costs, so a lower premium doesn’t become a higher bill for your team.
Every Option on the Table: Traditional small-group plans aren’t the only route. I’ll walk you through the alternatives that fit a business your size and explain how each one works, so you choose with the full picture.
My Help Costs You Nothing Extra: Insurers pay my commission, and plan premiums are generally the same whether you enroll through me or directly with the carrier, so you get personal guidance and ongoing support at no additional charge.
I Handle the Paperwork and Enrollment: I complete the group application with you, help your employees understand their choices and enroll, and follow everything through to approval, so you can get back to running your business.
You Reach Me Directly: You work with me directly, and I reply within 24 to 48 hours. When an employee has a claim or billing question, they can reach me too.
Licensed and Verified: I’m licensed in 33 states and write small-group plans for businesses with 50 or fewer employees. You can verify my license (Florida License #W323530, NPN #17946070) anytime through your state’s insurance department.
I Stay on Top of Your Renewal: I review your plan well before renewal, keep you informed of rate and rule changes through the year, and I’m here as your team grows or changes.
You can read all 25 reasons we should work together on my Why Choose Me page.
Group Health Insurance for Businesses With 50 or Fewer Employees
Small-group health insurance lets a business with 50 or fewer employees offer coverage to its team under one plan. ACA small-group plans can’t turn your business down or charge your group more because of an employee’s health history, which gives many owners more predictable options than they expect. Insurance companies usually set requirements for how many eligible employees enroll and how much of the premium the employer contributes, and I’ll explain how those rules work for each plan we look at.
You decide how much to contribute, which plan to offer, and whether employees can add a spouse or children. With some carriers, you can also offer more than one plan so employees can pick the level of coverage that fits them. I’ll walk you through the tradeoffs so you can set up benefits that work for your budget and your team.
Most of my clients are right here in South Florida, and I know the local health systems well, including HCA Florida, Memorial Healthcare System, and Baptist Health. That local knowledge helps me spot network issues that could affect your employees before they become a problem.
Health Coverage for the Self-Employed and Freelancers
If you work for yourself with no employees, a group plan usually isn’t available, but you still have solid options. I help self-employed clients, freelancers, and independent contractors compare ACA Marketplace plans and off-Marketplace plans for themselves and their families. Based on my own client records, I help about 148 individuals and families with ACA/Marketplace coverage each year.
Depending on your household income, you may qualify for financial help that lowers the cost of a Marketplace plan. Off-Marketplace coverage isn’t eligible for those savings, so I’ll show you where each option stands before you decide. Individual coverage generally has to be chosen during the yearly Open Enrollment Period or during a Special Enrollment Period after a qualifying life event, such as losing job-based coverage, and I’ll help you figure out whether a Special Enrollment Period applies to you.
This is also where having one agent for your whole household really helps. If you’re on your own plan while your spouse is on Medicare, or you’re stepping away from your business into retirement, I can help with both sides.
Dental, Vision, Life, and Supplemental Benefits for Your Team
Health insurance is usually the centerpiece of a benefits package, but it isn’t the only piece employees value. I can also help you add dental, vision, life, and supplemental coverage for your team, or for yourself if you’re self-employed. Keeping everything with one agent makes it easier to see how the pieces fit together and to keep track of renewals.
For owners, life insurance is often part of the picture too. I’ll help you figure out how much coverage makes sense for the people who depend on you and explain the difference between term and permanent coverage in plain language, so you know exactly what you’re buying.
When You or Your Employees Become Eligible for Medicare
Many small businesses have team members who are turning 65, and owners reach that point too. The rules for how Medicare works with a small employer’s plan are different from the rules at larger companies, and getting them wrong can lead to gaps in coverage or late-enrollment penalties. In general, if your business has fewer than 20 employees, Medicare usually pays first and the group plan pays second, so employees who are eligible for Medicare typically need to sign up for Part A and Part B on time. At businesses with 20 or more employees, the group plan usually pays first, and some employees may be able to delay Part B. Medicare also covers some people under 65 with a qualifying disability, and different employer-size rules can apply in that case.
I’ve spent the last 8 years focused on Medicare, and I specialize in helping people who are turning 65 or leaving employer coverage time their enrollment correctly. I can walk you and your employees through how Medicare and your group plan work together, so each person can make an informed decision.
Is Small Business Coverage Through Me Right for You?
Working with me is a good fit if you own a business with 50 or fewer employees and want to offer health benefits, if you already offer a plan and want a second look before renewal, or if you’re self-employed and need coverage for yourself and your family. It’s also a good fit if you’d like one agent who can help with your business coverage, your household’s individual plans, and Medicare when the time comes. The best way to start is a free plan review, where we talk through your business, your team, and your budget.
MORE WAYS I CAN HELP
Find the Right Coverage for Every Stage of Life
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:
Small Business Insurance FAQs
How Much Does It Cost to Work With You?
Nothing. My help comes at no extra cost to you, and plan reviews and quotes are free with no obligation to enroll. I’m paid a commission by the insurance company when you enroll in a plan through me, and that commission is already built into the plan’s premium, so you pay the same whether you enroll through me or directly with the carrier. Your actual yearly cost depends on the plan itself: premium, deductible, copays, drug costs, and out-of-pocket maximum. I give you a full-year estimate for each option, and all quotes are estimates until you’re enrolled.
What types of coverage can business insurance agents near me help with?
It depends on the agent and how they’re licensed. My focus for business owners is health and benefits coverage: small-group health insurance for businesses with 50 or fewer employees, individual health coverage for the self-employed, and dental, vision, life, and supplemental coverage. If you’re not sure which coverage fits your situation, we can talk it through during your free plan review.
How many employees do I need to offer a group health plan?
Small-group plans are designed for businesses with 50 or fewer employees. Insurance companies generally require at least one enrolled employee who isn’t the owner or the owner’s spouse, and they usually set minimum participation and contribution rules. Requirements vary by carrier and plan, so I’ll confirm the exact rules for every option we compare.
I’m self-employed with no employees. Can you still help me?
Yes. If you work for yourself, I’ll compare ACA Marketplace and off-Marketplace plans for you and your family, check your doctors and prescriptions, and look at your true yearly cost, not only the premium. Depending on your household income, you may qualify for financial help with a Marketplace plan.
Can I start a group health plan any time of year?
Generally, yes. Individual coverage is tied to Open Enrollment or a Special Enrollment Period, but small-group coverage can usually begin at different points in the year. Each plan then renews annually, and I review your plan and your options before every renewal. Start dates and paperwork deadlines vary by carrier, so it helps to reach out a few weeks before you want coverage to begin.
What happens when an employee becomes eligible for Medicare?
It depends mainly on the size of your business. If you have fewer than 20 employees, Medicare usually pays first, so an employee who is turning 65 typically needs to enroll in Part A and Part B on time to avoid gaps or penalties. If you have 20 or more employees, your group plan usually pays first. I help employees in either situation understand how Medicare and your plan work together so they can make an informed choice.
- How It Works
How we'll work together
Five steps, no pressure, and I stay with you after you enroll.
1
We talk about you
By phone, Zoom or face to face. Your health, your budget, your doctors.
2
I check the details
Doctors, hospitals, prescriptions and pharmacy, checked against each plan.
3
We compare real costs
A full-year estimate for each option, explained in plain language.
4
You decide, I enroll you
No pressure. If you choose a plan, I handle the application with you.
5
We review every year
Plans and networks change. I check yours each year and help with claims in between.
Book a Free Plan Review
Pick a time for a free 15-minute call by phone or video. I’ll check whether your doctors are covered, and my help never costs you 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.