2027 Virginia Open Enrollment
Open Enrollment Begins November 1

Get ready to compare 2027 health plans, review available financial assistance and see whether you may qualify for new Virginia Premium Savings.

Careers at Holloway Benefits Group • Virginia

Help Virginians find the right coverage, and build a career you're proud of.

Every day, our team helps families, seniors and small businesses across Virginia make sense of health insurance and Medicare. If you enjoy helping people, love explaining things clearly and want work with real purpose, we'd like to meet you, whether you're a seasoned agent or just curious about the profession.

A short, confidential, no-pressure conversation. No resume needed to start.

  • Independent agency
  • Licensed and new agents welcome
  • Remote within Virginia
  • Based in Hayes, Virginia
Why HBG

Support that helps you do your best work.

Insurance is a people business, and we invest in the people doing it. Here's what you get when you join HBG.

Hands-on ACA & Medicare training

Learn the plans, the rules and the enrollment systems, plus how to run a great client conversation, so you feel ready and confident.

Your toolkit, provided

A CRM, a business email address, a business phone line and our secure agent portal, all provided by the brokerage.

E&O coverage, handled

Errors & omissions insurance is covered by the brokerage, so you can put your energy into your clients.

The freedom of independence

We work with multiple insurance companies, so you can compare options side by side and recommend what truly fits each client.

A team in your corner

Work alongside experienced Benefits Consultants who are happy to share what they know. Questions are always welcome.

Work from anywhere in Virginia

Meet clients by phone, video or in person, from your home office or on the road. Full-time and part-time conversations are welcome.

What the work looks like

Work that makes a difference.

Health coverage and Medicare touch every part of people's lives: their doctors, their prescriptions, their budgets. Here's a look at what you'd actually be doing.

A day might include…

No two days are exactly alike, and that's part of the fun.

  • Helping someone new to MedicareExplain the choices in plain language and compare plans that work with their doctors and prescriptions.
  • Finding a family the right Marketplace planWalk them through their options and the financial help they may qualify for.
  • Being the person clients callAnswer questions, sort out billing or claim confusion with a carrier, and follow up.
  • Learning as you goPlan updates, carrier training and team conversations keep your knowledge current.

The rhythm of the year

Insurance has seasons. Here's the general shape of the year.

  1. Spring & summerLearn, certify, connectTraining and certifications for the new plan year, plus time to build relationships and review clients' coverage.
  2. Oct 15 – Dec 7Medicare Annual EnrollmentPeople with Medicare can review and change their plans. It's a busy and rewarding stretch.
  3. Starting Nov 1ACA Open EnrollmentVirginians shop for Marketplace coverage for the coming year, often with financial help.
  4. Year-roundLife changes don't waitNew jobs, moves, new babies and turning 65 can open enrollment opportunities any time of year.
Who we're looking for

Two ways in, one team.

Seasoned pro or brand new, what matters most is genuine care for people and a habit of following through.

Track A

Licensed agents

You know the business and you're ready for an independent home with real support behind you, plus the tools to keep growing.

You might be a great fit if…

  • Virginia resident Health (Accident & Sickness) license in good standing. Life & Annuities is a plus.
  • Experience with ACA/Marketplace plans, Medicare, or both.
  • Comfortable with CMS Medicare marketing rules and Virginia's Insurance Marketplace certification, or willing to get certified.

Already have a book of business? Let's talk. We tailor the conversation to your experience.

I'm licensed. Let's talk →
Track B

New to the profession

No insurance background? No problem. Agents come to this work from teaching, healthcare, customer service, banking, retail, the military and small business. If you enjoy helping people, you're already off to a good start.

You might be a great fit if…

  • You like helping people and explaining complicated things in plain language.
  • You're organized, follow through and are comfortable with technology.
  • You're willing to study for and pass the Virginia licensing exam. We'll explain each step.
  • You're at least 18 and live in Virginia (both are state requirements for a resident license).
I'm new. Tell me more →
The path to licensing

Your roadmap to becoming a health & Medicare agent in Virginia.

Getting licensed is a clear, step-by-step process. Here's how it works, from day one to helping your first clients. Licensing is handled by the Virginia State Corporation Commission's Bureau of Insurance.

  1. Choose your license lines

    To sell health coverage, including ACA plans and Medicare products, you need a Virginia Health license ("accident and sickness" insurance). Many agents add Life & Annuities.

    Bureau of Insurance
  2. Study for the exam

    Virginia doesn't require a pre-licensing course for Life & Annuities or Health. You can study on your own, though most people use an exam-prep course.

    Self-paced
  3. Pass the state exam

    Prometric runs Virginia's insurance licensing exams. You can take Health alone, Life & Annuities alone, or the combined Life, Annuities & Health exam.

    Prometric
  4. Apply & get fingerprinted

    Apply online through Sircon or NIPR. New resident applicants are also fingerprinted at a Fieldprint location for a background check. Processing usually takes about 15 business days.

    Sircon / NIPR
  5. Get carrier appointments

    Each insurance company you represent appoints you before you can sell its plans. We walk our agents through contracting and appointments.

    Carriers
  6. Certify for Medicare

    CMS requires agents who sell Medicare Advantage and Part D plans to be trained and tested every year. Most carriers accept AHIP's Medicare + Fraud, Waste & Abuse course, plus their own product certification.

    AHIP & carriers
  7. Certify for the Marketplace

    Virginia runs its own state-based exchange, so agents complete Virginia's Insurance Marketplace training and exam each year. HealthCare.gov certification isn't accepted in Virginia.

    Virginia's Marketplace
  8. Keep learning

    Virginia agents complete continuing education every two years, including ethics hours. We share CE opportunities with our team.

    Continuing ed

A general overview, not legal advice. Requirements and fees change, so check the official sources: Virginia Bureau of Insurance, Virginia's Insurance Marketplace and CMS.

Questions about getting started? Ask us →
FAQ

Good questions, straight answers.

Don't see your question? Call us at (757) 690-0255 or send it with the form below.

Do I need insurance experience to apply?

No. We welcome people who are new to the profession. What matters most is that you care about doing right by clients and are willing to learn. You'll need to earn your Virginia Health license before you can advise or enroll clients.

How does pay work?

We love talking about this one in person. Compensation and contract terms are discussed personally, based on your experience and any existing book of business you bring. We'll walk you through everything during the interview, so you'll have the full picture before making any decision.

What does HBG provide?

The brokerage provides your tools, including a CRM, a business email address, a business phone line and access to our secure agent portal. It also covers E&O insurance and provides ACA and Medicare training.

Is this full-time or part-time?

Full-time and part-time conversations are both welcome. Tell us what you're looking for on the form and we'll talk it through. Medicare's Annual Enrollment Period (October 15 – December 7) and ACA Open Enrollment are the busiest times of year.

Can I work remotely?

Yes. You can work remotely from anywhere in Virginia and serve clients by phone, video or in person. New agents get a Virginia resident license, which requires a Virginia home address.

What's the difference between being licensed and being appointed?

Your state license, from the Virginia Bureau of Insurance, lets you sell health insurance. An appointment is a separate step: each insurance company has to appoint you before you can sell its plans. Medicare plans also need yearly certification. We help you through the appointments once you're licensed.

What's the difference between a captive and an independent agency?

A captive agent represents one insurance company and sells only its products. An independent agency like HBG works with multiple insurance companies, so we can compare options and recommend what fits each client.

What happens after I submit the form?

We'll review your information and reach out to set up a short, no-pressure conversation about your goals and whether this work is a good fit. Sending the form doesn't commit you to anything.

Start a conversation

Ready to take the next step? Let's talk.

Licensed or just curious, this is where it starts. Tell us a little about yourself and we'll reach out to set up a friendly, no-pressure conversation.

Prefer to call?(757) 690-0255
Holloway Benefits GroupPO Box 31, Hayes, VA 23072
  1. Send a quick noteJust a few questions. No resume needed.
  2. Have a conversationWe'll get to know you, answer your questions and talk through how things work, including pay and contract terms.
  3. Map your next stepsNew to insurance? We'll point you along the licensing path. Already licensed? We'll talk about getting you set up.
Your next chapter could start with one conversation. We'd like to hear your story.

Let's get to know you

Fields marked optional can be skipped.

Are you currently licensed?
License types held (optional)
Looking for (optional)
Years of insurance experience

No resume needed now. We'll ask later if it's helpful.

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