Know what you’re paying for.
Know what your crew is getting.

A review of what your business can carry and what is available to a team your size. Three options come back, each with the reason it made the list.

Three options, with the reasoning Straight about cost and limits Still there at renewal
12
$50

$50 is a common way in. Move it toward $100 if the business can carry more.

75%

Your guess, not ours.

What it costs the business

$450 a month

What your team can pick from

  • Telehealth + mental health
  • Accident
  • Critical illness
  • Hospital indemnity
  • Short-term disability
  • Life insurance

Estimate only. Not a quote, not an offer of coverage, not tax advice. What you would actually pay depends on who enrols and what is available to your group.

What you actually end up with.

You know what you are paying for and why, HR can explain the options, and your team knows somebody spent money on them on purpose.

A strategy you can afford

The financial commitment is decided first, not discovered at the end.

Benefits people actually use

Coverage chosen by the person who has to use it, explained in their words.

Participation that reflects reality

Coverage through a spouse gets documented instead of reading as a no.

Renewals stop ambushing you

Next year starts from a strategy, not a letter.

Choices you can explain

Three real options you can defend to your business partner, with the reasoning attached.

Somebody who says no

If the honest answer this year is not yet, you hear that.

The employer puts in $50
Life insuranceAmount and terms depend on the carrier quoted
Short-term disabilityIncome protection when they cannot work quoted
2 items chosen$46.00
Employer contribution−$46.00
Their part

Rates: Vector Employer Solutions, approximate bi-weekly averages shown as monthly equivalents. An illustration, not a quote.

How the money works

Sometimes the answer is a set amount per person, per month.

For a business that has never offered anything, the simplest way in is a fixed employer contribution — say $50 to $100 per employee per month — put toward a menu each person picks from. It works for the employee whose medical already comes through a spouse: something through their own employer instead of nothing.

$50 a month does not buy comprehensive major medical, and nothing here implies it does. Whether a contribution model fits your business is an answer from the review, not from this page.

Your team is carrying more risk than you think.

Figures about the market you are operating in, not predictions about your business. Nobody has studied your shop.

Half

could not cover a $1,000 bill

50% of small-business employees say they could not pay $1,000 in out-of-pocket costs. Across companies of every size it is 44%, so people at small businesses are the more exposed group.

Aflac WorkForces Report, 2025 · small-business employees · Aflac sells these products · source
90% vs 34%

want it; get it

90% of employees say the need for supplemental coverage is growing. Only 34% of employers offer any.

Aflac, 2025 · all company sizes · supplemental here means dental, life and vision · source

Context on the hiring market, not a claim about benefits. About 4 in every 100 accommodation and food services workers quit each month in 2025, and 82% of small-business owners who were trying to hire that August reported few or no qualified applicants. Sources.

Photograph
to come

Who you would be working with

A working partner, not a sales-first quote guy.

Matt Ragudo’s own line, and the job description. A licensed insurance professional: over a decade in financial planning at wealth-management firms, then a health insurance agency with 60 licensed agents, then claims advocacy, standing between patients and insurers when a bill made no sense. Hawaii originally, three years in Fukuoka on the JET Programme, Texas since 2021.

10+ years

financial planning

60 agents

the agency he ran

Claims side

a previous role

Aloha, y’all

Hawaii, Japan, now Texas

Frequently asked questions

The things owners actually ask on the first call.

Photograph
to come

It depends what you end up with. Group medical is one of the things in scope. But where the answer is a modest employer contribution toward supplemental benefits, that is not major medical: $50 a month does not buy major medical, and nobody here will tell you it does.

You can ask to see more. But wading through an overwhelming number of plans is how these decisions stall for five years. Three options, weighed against what the company can afford and what you want employees to receive — and the reasoning is the deliverable.

Both are in scope: group medical consulting, supplemental health, medical expense reimbursement plans and wellness-integrated programmes. None is right by default, so they get evaluated together rather than claimed on a website. Your CPA belongs in that conversation.

Yes. Those employees can still receive something through their own employer rather than nothing, and documenting a spouse waiver makes the enrolment picture reflect what is actually happening. What a carrier makes of that depends on the carrier and your group.

It may be worse on paper than it is in life. Getting eligibility and waivers right starts with finding out who is actually covered elsewhere and documenting it. What that means for your group is what the review is for.

Worth asking rather than assuming. The review establishes what is genuinely available to a group your size, starting with an accurate eligibility and waiver picture, because a headline enrolment number often understates what is going on.

Start with what is already in place: what is worth preserving, what needs improving, and getting you ready for the first renewal under your ownership.

Worth checking, and that is a standing part of the job. What suits nine people in one location rarely suits thirty across two, so the strategy gets reassessed as headcount and needs change.

Renewal is the point of having an adviser rather than a signup: what you can plan for, which decisions are genuinely in your control, and how the strategy should respond.

Whoever handles HR gets the options explained so they can help select plans that suit your people, and the programme is explained to employees directly. The test is whether they can explain it afterwards with nobody else in the room.

Sometimes they could, and you will be told when that is the honest answer. For some products the access, pricing or underwriting through a group differs from what an individual faces — but only where that is true of the specific policy, so you get shown where the advantage sits and where there is not one.

You set the eligibility rules, within what each carrier and benefit allows. Full-time only, after 60 days, whatever fits how you staff — written down so it stays consistent.

Ask your CPA. Tax treatment depends on how the arrangement is structured and on your business, and this page is not going to decide it. Nobody here is your accountant.

That is a reason to look at it rather than skip it. The roster moves person by person, not as one all-or-nothing decision, and waiver documentation matters more when people come and go, not less.

Then that is the answer you get, including when an option is plainly unfavourable. Not this year, and here is what to sort out first, beats being sold something that does not fit.

Nothing. Thirty minutes, and you leave with a clearer view of what your business could carry and what that would put in front of your team.

Where every number on this page comes from

Each figure below was checked against the original report, not a summary of it. Where a survey measures something narrower than ’businesses with 5 to 49 people’, that is said plainly. None of these studies show cause and effect, and none of them is a claim about what this service would do for your business.

  1. 50% of small-business employees could not cover $1,000 in out-of-pocket costs (44% across all company sizes). Aflac, 2025–2026 WorkForces Report, small-business fact sheet. Kantar; 2,000 U.S. employees at companies with three or more employees, April–May 2025. Aflac defines small business as fewer than 100 employees and sells supplemental insurance. aflac.com
  2. 90% of employees say the need for supplemental insurance is increasing; 34% of employers offer it. All company sizes. Aflac defines supplemental insurance here as dental, life and vision. Aflac, 2025–2026 WorkForces Report. aflac.com
  3. 4.2% of accommodation and food services workers quit every month in 2025; 2.6% in retail. Monthly rates, not annual. U.S. Bureau of Labor Statistics, Job Openings and Labor Turnover Survey, 2025 annual figures. bls.gov
  4. 82% of hiring small-business owners got few or no qualified applicants; 35% had an unfilled opening. The base is owners who were trying to hire, not all owners. NFIB, Small Business Economic Trends, August 2026. 476 usable responses. nfib.com

Deliberately not used here: replacement-cost-per-employee dollar figures, whose commonly cited versions rest on research from 2006 to 2012; and employer-opinion surveys about whether benefits improve retention, which measure opinion rather than measured turnover.

Thirty minutes. No slides. No pressure.

Bring your headcount and a number you could live with. You get a straight answer on whether this fits your shop or it doesn’t.

Book the 30-minute call