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 dusk

Licensed advisors · Hayes, Virginia

Health coverage, handled personally.

Holloway Benefits Group advises individuals, families, Medicare beneficiaries and employers across Virginia — one considered conversation at a time.

Schedule a consultation or call (757) 690-0255

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

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.

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 Insurance Dental & Vision

The Holloway approach

Advice first. Then a recommendation.

First
A conversation
We learn what you have today, what matters to you and what you are trying to solve.
Then
A clear comparison
Plans, networks, benefits and costs, laid side by side and explained without jargon.
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.

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 HollowayAgency Manager

Kimberly WaltersSenior Benefits Consultant

Jessica FelderSenior Benefits Consultant

Chava SimpsonSenior Benefits Consultant

Arianna GilesBenefits Consultant

Jaewoo YiBenefits Consultant

Alex McClennyBenefits 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.

Full name

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We'll only use your details to respond to you. There is no obligation.

Sorry, your note didn't go through. Please call us at (757) 690-0255 or email info@hollowaybenefits.com.

Thank you.

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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