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Trusted Advisors, Not Salespeople

The Future of Insurance Guidance.

Medicare, ACA & Life Insurance made simple by licensed advisors who put your needs first.

Human Experts · Modern Technology · Personalized Solutions

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What can we help you with?

LEARN FIRST · NO FORMS

Takes 30 seconds. No pressure — just clarity.

Free consultation with a licensed advisor. Calling this number will connect you with a licensed insurance agent. We do not offer every plan available in your area.

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Choose Your Coverage

One conversation. Every option, explained.

Tell us what matters to you. We'll explain your options in plain language — in English or Spanish.

Medicare

Turning 65? Medicare, explained clearly.

Advantage or Supplement? What does Part D actually cover? We answer the questions everyone has — before recommending anything.

  • Turning-65 guidance and enrollment-period help
  • Medicare Advantage & Medicare Supplement comparisons
  • Part D drug plans checked against your medications & pharmacy
  • We verify your doctors are in network first
  • Extra benefits some plans offer: dental, vision, OTC, transportation, food cards*
  • Bilingual guidance — English & Spanish
Talk to a Medicare Advisor

Carriers we work with: Humana · Aetna · UnitedHealthcare · CarePlus · Elevance · HealthSun · BCBS · Devoted

*Plan benefits, premiums, and availability vary by carrier, county, and eligibility. We do not offer every plan available in your area. Currently we represent multiple organizations which offer various products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program to get information on all your options.

▶Educational video2-minute explainer — what it is, who qualifies, main benefits, common questions.
▶Educational video2-minute explainer — what it is, who qualifies, main benefits, common questions.
ACA / Marketplace

Health coverage your family can actually afford.

We check whether you qualify for Marketplace subsidies and walk you through every option — without the jargon.

  • Subsidy eligibility help
  • Self-employed families and independent workers
  • Lost Medicaid or employer coverage — Special Enrollment help
  • Immigrants with eligible legal status
  • Year-round Special Enrollment Period guidance
Check My Marketplace Options

Carriers we work with: Oscar · Ambetter · AmeriHealth · BCBS · Cigna · Molina · AvMed · 22 Health · Wellpoint / Anthem

Eligibility for subsidies depends on household income, household size, location, and other eligibility factors. Enrollment in a plan may be limited to certain times of the year unless you qualify for a Special Enrollment Period.

Life Insurance

Protect the people who count on you.

From a child's first policy to mortgage protection and income replacement — coverage built around your family and your budget.

  • Term life & whole life
  • Mortgage protection & income replacement
  • Final expense coverage
  • No-medical-exam options
  • Children's policies
Get a Life Insurance Game Plan

Carriers we work with: Foresters · American Home Life · MassMutual · Mutual of Omaha · Kansas City Life · United Home Life · Corebridge Financial · SBLI · ELCO Mutual · Banner Life · Royal Neighbors · F&G · American Amicable · Baltimore Life · Mutual Trust · Transamerica · John Hancock

Life insurance approval, rates, and coverage amounts may depend on underwriting, age, health, carrier guidelines, and state availability.

▶Educational video2-minute explainer — what it is, who qualifies, main benefits, common questions.
Why WIN Insurance Group

Trusted Advisors, Not Salespeople.

The difference is in how we work — and who we work for.

PILLAR 01

Advisors, not closers

No pressure, no scripts, no call-center runaround. Real people helping real people make informed decisions.

PILLAR 02

Bilingual guidance

English and Spanish today — with Creole, Portuguese, and more languages on our roadmap.

PILLAR 03

Carrier-neutral comparisons

We represent multiple organizations and explain the trade-offs honestly so the choice is truly yours.

PILLAR 04

Modern tools, human judgment

Technology to compare plans faster. Licensed humans to help you decide better.

About WIN

Every policy has a person behind it.

A family trying to protect their future. Someone turning 65 and overwhelmed by Medicare. A parent searching for affordable health coverage. A loved one wanting to leave their family protected.

WIN Insurance Group was created to help people make these decisions with confidence. We believe insurance should be simple, transparent, and centered around the client — not the carrier.

By combining experienced advisors, innovative technology, and a commitment to service, we've helped thousands of families find coverage that protects what matters most.

We're not a call center. We're real people helping real people make informed decisions every day.

Insurance For Winners.

Book a Free Consultation
Meet the WIN Team

Meet Your WIN Advisors

Trusted professionals dedicated to helping you make confident insurance decisions.

Andres Wulff, Senior Insurance Advisor at WIN Insurance Group

Andres Wulff

Senior Insurance Advisor

Andres specializes in helping individuals, families, and Medicare beneficiaries navigate complex insurance decisions with confidence. Over the past six years, he has helped thousands of clients compare coverage options, understand their benefits, and choose plans that align with their healthcare and financial goals. His approach is simple: educate first, advise second, and always put the client’s needs first.

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Juan Pablo Wulff, Insurance Advisor at WIN Insurance Group

Juan Pablo Wulff

Insurance Advisor

Juan focuses on making health insurance easy to understand for families, individuals, and those exploring Medicare options. Known for his patient and educational approach, he helps clients compare plans, understand costs, and find coverage that fits their unique situation. His goal is to ensure every client feels informed, comfortable, and confident in their decision.

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Rolando Garcia, Insurance Advisor at WIN Insurance Group

Rolando Garcia

Insurance Advisor

Rolando works closely with individuals and families seeking life insurance, Medicare solutions, and long-term protection strategies. He believes insurance should be straightforward, transparent, and tailored to each person's needs. By taking the time to understand every client's goals, Rolando helps families protect what matters most while planning for the future.

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Meet all 25 WIN advisors →

Client Stories

What families say about WIN.

Real reviews from real clients — shown exactly as they wrote them.

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Our Carrier Network

Access to Leading Insurance Carriers

Every carrier below links to its official website. Or skip the homework — a WIN advisor compares them around your doctors, medications, and budget.

Medicare

HumanaAetnaUnitedHealthcareCarePlusElevanceHealthSunBCBSDevoted

ACA / Marketplace

OscarAmbetterAmeriHealthBCBSCignaMolinaAvMed22 HealthWellpoint / Anthem

Life Insurance

ForestersAmerican Home LifeMassMutualMutual of OmahaKansas City LifeUnited Home LifeCorebridgeSBLIELCO MutualBanner LifeRoyal NeighborsF&GAmerican AmicableBaltimore LifeMutual TrustTransamericaJohn Hancock

Carrier names, logos, and trademarks belong to their respective owners; links are provided for convenience and do not imply endorsement. We do not offer every plan available in your area. Currently we represent multiple organizations which offer various products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program to get information on all your options.

Always Available

Meet your Virtual WIN Advisor.

Not sure where to start? Ask in English or Spanish. The Virtual Advisor helps you understand what type of coverage fits your situation — then connects you with a licensed agent. It never enrolls you in anything on its own.

  • Answers simple coverage questions, 24/7
  • Bilingual — English y español (more languages coming)
  • Guides you to the right team: Medicare, ACA, or Life
  • Always routes to a free appointment with a licensed agent
Education Center

Understand it before you sign it.

Plain-language guides written by licensed advisors — no jargon, no pressure. Click any topic to read the full guide and get your checklist.

Educational content only — not enrollment advice for any specific plan. We do not offer every plan available in your area. Currently we represent multiple organizations which offer various products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program to get information on all your options. Eligibility for ACA subsidies depends on household income, household size, location, and other factors. Life insurance approval, rates, and coverage amounts may depend on underwriting, age, health, carrier guidelines, and state availability.

FAQ

Questions everyone asks.

Does it cost anything to talk to a WIN advisor?

No. Consultations are free. Advisors are compensated by insurance carriers when you enroll in a plan, and that compensation never changes your premium.

Do you work with every insurance company?

No. We do not offer every plan available in your area. We represent multiple organizations which offer various products in your area. For information on all your Medicare options, contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program.

When can I enroll in Medicare or a Marketplace plan?

Enrollment in a plan may be limited to certain times of the year unless you qualify for a Special Enrollment Period. Life events like turning 65, losing Medicaid, losing job coverage, or moving can open enrollment windows — an advisor can check yours.

¿Hablan español?

Sí — hablamos español. You can request a Spanish-speaking advisor on any form, by phone, or in the chat. Creole and Portuguese support are on our roadmap.

Will you check my doctors and medications before recommending a plan?

Yes — always. We verify your doctors, your medications, and your preferred pharmacy before recommending any plan.

I lost my Medicaid coverage. What now?

You may qualify for a Special Enrollment Period and, depending on your household income and size, for Marketplace subsidies. Eligibility for subsidies depends on household income, household size, location, and other eligibility factors.

What states do you serve?

We're a Florida-based agency licensed in 8 states: Florida, Georgia, North Carolina, South Carolina, Tennessee, Texas, Colorado, and Arizona.

Are you part of Medicare or the government?

No. WIN Insurance Group is not connected with or endorsed by the U.S. government or the federal Medicare program. We're an independent agency of licensed insurance advisors.

Book Your Free Consultation

Let's find your coverage.

Tell us a little about what you need. A licensed advisor — not a call center — will reach out at the time you choose.

Call or text305-721-8381

Calling this number will connect you with a licensed insurance agent.

Office1750 NW 107th Ave, North Mezz #10
Miami, FL 33172
Emailinfo@wininsurancegroup.com
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Medicare Questionnaire

Medicare details

We do not offer every plan available in your area. Currently we represent multiple organizations which offer various products in your area. Please contact Medicare.gov, 1-800-MEDICARE, or your local State Health Insurance Program to get information on all your options. Not connected with or endorsed by the U.S. government or the federal Medicare program.

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