One founder is
a group of one.
We can cover it.
You do not need five employees to get real group health insurance, a benefits portal, and someone who answers the phone. Waugh Agency builds and runs coverage for startups with a single founder, self-employed owners, and employer groups with fewer than five people enrolled on medical.
Too small for a broker. Too complicated for a website.
At one to four enrolled lives, most agencies decline the case, or take it and never call again. The founder ends up on a marketplace plan chosen in a browser tab at 11pm, and nobody ever checks whether a group plan would have been cheaper, richer, or both.
We work this size on purpose. Modern benefits technology is what makes it possible — the same platform and compliance calendar a 200-life employer gets, sized for a company that does not have an HR department yet.
We test group eligibility first
A one-person company can often qualify for small-group coverage — and often cannot. It turns on entity type, payroll records, whether the owner draws W-2 wages, and each carrier's own participation rules. We confirm all of it before anything is submitted, so nothing gets rescinded after the fact.
Group and non-group, priced side by side
Small-group medical, the individual marketplace, an ICHRA, a spouse's plan, COBRA if you just left a job — each with a real number attached. You see all of them in writing, including the honest case for changing nothing.
Enrollment, and the portal switched on
We complete the carrier paperwork and stand up Employee Navigator for groups of two or more — at no cost to you, because the agency absorbs the subscription. Online enrollment, employee documents and payroll integration from day one, so hire number three does not become a spreadsheet problem.
Then we stay for the plan year
Adds and terms are unlimited. Claim disputes, ID cards, billing errors, a mid-year move, COBRA and state continuation notices — ours to handle. And a real renewal review every year, not a forwarded rate letter.
Three routes to coverage. One point of contact.
The right answer at this size is genuinely different from case to case. We price all three before recommending one.
Small-Group Coverage for 1–4 Lives
Real employer-sponsored medical, dental and vision — frequently available to a company with a single W-2 founder, and often the better economics when it is.
- Carrier eligibility & participation review
- Fully insured and level-funded quoting
- HSA, HRA and FSA pairing
- Small Business ACA Tax Credit screening
- State & federal SHOP small business market
- Group life & disability at small-group rates
Non-Group & Self-Employed Routes
When a group plan is not available or not the best number, the individual market is not a consolation prize — it just needs to be shopped properly.
- On- and off-exchange individual & family plans
- ICHRA and QSEHRA reimbursement arrangements
- COBRA alternatives & special enrollment windows
- 1099 contractors & owner-only entities
- Medicare-eligible owners & the bridge to 65
- Global & travel medical for remote founders
Administration & Compliance
The part that scales badly. Employee Navigator's built-in AI, automated compliance tracking and 600+ integrations are what let a small group get large-employer service.
- Employee Navigator at no cost (2+ employees)
- Onboarding, online enrollment & e-signature
- ERISA wrap & Section 125 documents
- COBRA & state continuation notices
- State leave programs & PFML exemptions
- 600+ carrier, payroll & TPA integrations
Why a group plan is worth testing first.
A self-employed person with a business entity often has two doors open, not one. The differences are structural, not marketing. Availability varies by state and by carrier — which is exactly why it is worth checking rather than assuming.
The question is never whether you are big enough for a group plan. It is whether anyone has actually checked.
If one of these is you, start with a conversation.
We work with companies before they look like companies. Most of these calls come in the month something changes.
The solo founder
You incorporated, you are on payroll, and you just left a job with coverage. A group plan of one is frequently available and frequently cheaper. Worth ten minutes to find out.
The first two or three hires
Benefits just became a recruiting problem. You need something you can put in an offer letter, and a system that will not fall apart at employee number six.
The consultant or practice owner
Independent for years, no employees, and tired of re-shopping the marketplace every November without knowing whether you are leaving money behind.
The group that shrank
You were eight, now you are three, and your carrier is asking questions about participation. There is usually a way to hold the plan — but not by ignoring the letter.
The owner turning 65
Staying on the company plan, moving to Medicare, or running both — with real deadlines and permanent penalties attached to getting the order wrong.
The distributed team
Two founders in Boston, one engineer in Brooklyn, a designer abroad. Multi-state and international coverage is routine work for us, not an exception.
Rooted in the Northeast. Licensed nationwide.
Our home ground runs from Boston, Andover and Worcester out through Western Massachusetts, the Cape and the North and South Shores, down through Connecticut, New York City and all five boroughs, Long Island, New Jersey and Philadelphia, plus New Hampshire and Maine. That is where we know the carriers, the networks and the hospital systems by name — which matters more at four lives than at four hundred, because you have fewer plans to choose between.
Beyond it we serve clients in all 50 states, directly where we are licensed and through trusted affiliates where local knowledge counts. A founder in Austin and an employee in Providence is a normal week.
Independent, and not owned by a carrier
There is no house plan we are expected to place. NAHU-accredited and AHIP-certified, recertified annually. More on our about page.
Tech-forward because it is the only way
AI-assisted plan building, automated eligibility and compliance tracking, and 600+ carrier and payroll integrations are what let a small agency give a four-life group large-employer service. Employee Navigator acquired Ease in 2023, and through 2026 we are moving every client onto the modern portal.
Run the tax credit before you decide
Employers under 25 full-time-equivalent employees with average wages below the threshold can claim a credit worth up to half of what they contribute, for two consecutive years. Our free Small Business ACA Tax Credit Calculator gives you the number in a minute.
Built to be grown out of
Everything we set up at four lives — the portal, the plan documents, the compliance calendar — is the same system we run for employers many times that size. Nothing gets rebuilt when you cross five.
Tell us how many people are on the plan.
Even if the answer is one. Submit the form and a licensed broker will be in touch within one business day — or call us and we will look at it together on the phone.