Serving Virginia | Health Insurance | Medicare
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HOLLOWAY
BENEFITS GROUP
Guidance • Protection • Peace of Mind
2027 Virginia Open Enrollment
2027 Open Enrollment Is Open

Nov 1, 2026 – Jan 29, 2027. Enroll by Dec 31 for coverage starting Jan 1.

Get Enrollment Help → Learn About 2027 Savings ↗
Open Enrollment is open now. MedicareOct 15 – Dec 7, 2026 Review Medicare Virginia MarketplaceNov 1, 2026 – Jan 29, 2027 Review ACA plans
The George P. Coleman Bridge over the York River at Yorktown, Virginia, at duskA grandfather and grandson walking hand in hand along a park pathA smiling grandfather and grandson sitting together on a boat by the waterA senior couple laughing together on a sofa at homeA smiling senior woman relaxing at a park tableGrandparents with their grandchildren outdoors among flowers

The York River · Yorktown, Virginia — Photo: “Coleman Bridge Yorktown” by Matthew Atkinson, CC BY 3.0, via Wikimedia Commons; cropped and toned.

Medicare · Health · Life Insurance — Hayes, VA

Medicare, health & life insurance for the people you love.

Compare Medicare and ACA health plans with a licensed local advisor — side by side, in plain English, at no additional cost to you.

Book a Free Consultation Call 757-690-0255

By calling, you’ll speak with a licensed insurance agent · TTY 711. Not affiliated with or endorsed by the U.S. government or the federal Medicare program.

65 or turning 65Medicare

Medicare Advantage, Medicare Supplement and Part D options, compared side by side.

Explore Medicare Under 65Health / ACA

Individual and family health plans for Virginians, explained in plain English.

Explore health plans Every stage of lifeLife Insurance

Term and permanent coverage to protect the people who count on you.

Explore life insurance
  • 8 licensed agents
  • Licensed in Virginia
  • Medicare · ACA · Life
  • No additional cost for our help
Where are you today?

Start with your situation, not a product.

Choose the path that fits. We compare options from the carriers we represent, explain the trade-offs in plain language and stay with you after you enroll.

i.
Individual & Family Health

I buy my own health coverage

Virginia Insurance Marketplace plans, networks, deductibles and available financial assistance.

 ii.
Medicare

I’m turning 65, or already on Medicare

A careful review of Medicare options around your doctors, prescriptions and budget.

 iii.
Employer Benefits

I run a Virginia business

Group health and ancillary benefits to help you recruit, retain and support your team.
Also availableLife InsuranceDental & Vision
The Holloway approach

Advice first. Then a recommendation.

  1. First

    A conversation

    We learn what you have today, what matters to you and what you are trying to solve.

  2. Then

    A clear comparison

    Plans, networks, benefits and costs, laid side by side and explained without jargon.

  3. After

    A lasting relationship

    Questions, changes and renewals come back to the same local team, long after enrollment.

Built around you, not one carrier

One advisor. Many carriers.

We compare plans from multiple carriers, so our recommendation starts with your doctors, prescriptions and budget, not with a single company's plans. We work with many of Virginia's most established carriers.

  • Anthem HealthKeepers
  • Sentara Health Plans
  • UnitedHealthcare
  • Aetna
  • Cigna Healthcare
  • Humana
  • Delta Dental
  • VSP Vision Care
Carrier availability varies by plan type and county. Logos are trademarks of their respective owners.
Our advisors

The people you will actually speak with.

Licensed benefits professionals based in Virginia. You will know your advisor by name, and they will know your situation.

Meet the full team
Jared Holloway, Agency Manager at Holloway Benefits Group
Jared HollowayAgency Manager
Kimberly Walters, Senior Benefits Consultant
Kimberly WaltersSenior Benefits Consultant
Jessica Felder, Senior Benefits Consultant
Jessica FelderSenior Benefits Consultant
Chava Simpson, Senior Benefits Consultant
Chava SimpsonSenior Benefits Consultant
Arianna Giles, Benefits Consultant
Arianna GilesBenefits Consultant
Jaewoo Yi, Benefits Consultant
Jaewoo YiBenefits Consultant
Alex McClenny, Benefits Consultant at Holloway Benefits Group
Alex McClennyBenefits Consultant
Tina Donnell, Group Benefits Consultant
Tina DonnellGroup Benefits Consultant
Begin here

Begin with a conversation.

Choose a time that suits you, or send a short note if you would rather we reach out. A consultation is a relaxed phone conversation about where you are and what you need. There is no cost to speak with us.

Prefer to call? (757) 690-0255
Prefer email? info@hollowaybenefits.comOn Medicare or turning 65? Book a Medicare Plan ReviewServing all of Virginia
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Send us a note.

A member of our team will follow up with you personally.

I'd like to talk about
We'll only use your details to respond to you. There is no obligation.

Thank you.

Your note is on its way to our team. We'll be in touch soon. If it's urgent, call (757) 690-0255.

Careers at HBG

Love helping people? Build a career with us.

We're growing our team of Benefits Consultants across Virginia. Whether you're a licensed agent or brand new to insurance, we'd like to meet you.

  • ACA & Medicare training
  • Tools & E&O provided
  • Remote within Virginia
Start a conversation → Explore careers