Health Insurance for Fractional CFOs, CMOs, COOs and CTOs

What changes when you go fractional

The pattern is familiar. You step out of a full-time CFO, CMO, COO or CTO seat, sign two or three part-time engagements, and bill each company through your own LLC or on a 1099. For insurance purposes you are now self-employed. None of those clients owes you coverage, and in most cases their group plans are written for employees, not outside contractors. Some fractional leaders also hold advisory board seats or take a small equity stake in a client, which makes the income picture even harder to pin down.

That leaves three realistic paths: COBRA from your former employer, a private medically underwritten plan, or a Marketplace plan. For a healthy household I usually start with the private plan, because its premium is set by age, ZIP code and health instead of income. You answer health questions to apply, approval depends on those answers and is not guaranteed, and benefits and pre-existing condition rules vary by plan. Private plans are not ACA Marketplace plans, so I lay all three options out together before you choose.

The COBRA decision

COBRA feels like the safe default because nothing visible changes: same doctors, same deductible, same card in your wallet. What changes is who pays. Federal COBRA applies to employers with 20 or more employees, lasts up to 18 months and can cost up to 102 percent of the full premium, meaning the portion your employer used to cover, your own portion and a small administrative fee. On a generous executive plan for a family, that monthly bill often surprises people.

Four questions settle most COBRA decisions:

1. How much of this year's deductible have you met? If most of it is behind you, riding COBRA to the end of the plan year can be reasonable.
2. Is anyone in active treatment? Switching plans in the middle of care has a real cost, and COBRA keeps things continuous.
3. How healthy is everyone on the plan? If the whole household is a good candidate for underwriting, a private plan deserves a quote next to COBRA's full price.
4. Does your separation agreement pay for COBRA? Some packages cover the premium for a set number of months, which changes the timing of any switch.

You also do not have to decide on your last day. You get a window to elect COBRA, and once it is elected and paid it reaches back to the day coverage ended. That lets you apply for a private plan with COBRA held in reserve, and elect it only if underwriting does not go your way. Our COBRA alternatives guide goes further into the trade-offs.

Many clients, one income projection

The Marketplace sizes its credit on household income for the full calendar year, so a fractional leader has to total every engagement before the year starts. That forecast breaks easily. One client extends your contract, another ends it early, a third shifts part of your retainer into equity. And the year you leave a full-time role already holds months of salary, maybe a final bonus and possibly severance, all of which count.

Here is how the 2027 Marketplace rules play out for portfolio income:

• Rates are up again. KFF's review of 2027 filings from 276 Marketplace insurers found a median proposed increase of 15 percent, on top of a steep rise for 2026.
• The credit has a hard edge. For 2027, help stops at 400 percent of the federal poverty level: $63,840 for one person, $86,560 for two, $109,280 for three and $132,000 for four. One dollar over and the credit is zero.
• Advance credit can come back as a bill. If you take an advance credit on a projection and the year closes above the line, you repay the whole advance on Form 8962. A single new client signed in the fall can be enough.
• Coverage built around one metro area. Many Marketplace plans are HMO or EPO designs with a local network and little or no coverage outside it except emergencies.
• A large exposure before the plan pays in full. The 2027 out-of-pocket maximum is $12,000 for one person and $24,000 for a family.
• A fixed enrollment season. On HealthCare.gov, open enrollment runs November 1, 2026 to January 15, 2027, with December 15 the deadline for a January 1 start. States that run their own exchange set their own dates. Outside that season you generally need a qualifying event.

For reference, the Bureau of Labor Statistics put the median annual wage for chief executives at $213,990 in May 2025 and listed 27 percent of chief executives as self-employed. A household earning anywhere near that median is past even the four-person line of $132,000.

Why underwriting suits a portfolio career

A fractional practice is built to flex. Clients come and go, rates rise as your reputation grows, and revenue rarely looks the same two quarters in a row. A plan priced on health rather than earnings fits that shape:

• Your premium ignores your invoices. Your client count is not part of how a private plan is priced.
• Start dates follow your schedule. If approved, coverage can begin on the first of a month you choose, whether that is the month COBRA ends or the month a new engagement starts.
• Networks that travel. Many private plans use national PPO networks, which helps when your clients sit in Texas, North Carolina and Georgia and you split time among them. Confirm how a specific plan handles care away from home, since networks vary.
• No year-end true-up. There is no premium tax credit involved, so nothing about the policy depends on what your return shows.

Your LLC, your S corporation and the premium

How your practice is organized decides how the premium is reported. The self-employed health insurance deduction is generally open to sole proprietors, partners and shareholders owning more than 2 percent of an S corporation. For those shareholders, the corporation usually pays or reimburses the premium and reports it as wages first. The deduction belongs to the business that establishes the plan, cannot exceed that business's net earnings, and is not available for any month you were eligible for a subsidized employer plan, including one through a spouse. The same rules apply whether you hold a private plan or a Marketplace plan. General information, not tax advice — confirm with your CPA based on your specific entity structure.

A spouse's plan is worth a look

If your spouse works for an employer that offers family coverage, price it before you buy anything. Joining a spouse's plan after you lose your own coverage is usually allowed under that plan's special enrollment rules, and it can be the simplest answer while your client list settles. Compare what the spouse's employer charges to add you with what a private plan or Marketplace plan would cost for you alone. I will put it next to the private and Marketplace numbers so you can see the whole picture.

A clean transition, step by step

1. Get the exact date your employer coverage ends, in writing, before your last day.
2. Read the COBRA notice when it arrives and note the election deadline.
3. Apply for a private plan with a requested start on the first of the month after coverage ends, so there is no gap if you are approved.
4. If underwriting declines you or a family member, either elect COBRA before its deadline or enroll on the Marketplace within the 60-day special enrollment period that losing job coverage opens.
5. Revisit the plan each year as your client mix and household change.

When the Marketplace is the better answer

The Marketplace is the right home for some fractional executives, and I will tell you if you are one of them. If you or a family member has a significant health condition, the Marketplace must accept you during open enrollment or a special enrollment period and cannot price you on health. It can also win in a first fractional year that will honestly finish under the line for your household size, because the credit may make the Marketplace the better value. Disability, accident and critical illness coverage are separate policies whose contents vary by plan, and I can review those separately if they matter to you.

Let's compare your options

Everything runs by phone or video, in English or Spanish, and I am licensed in 31 states, including Florida. Send your ZIP code, the ages on the plan, your COBRA quote if you have one and a short health summary, and I will build a side-by-side. You can get a quote or call (786) 218-2384. Other roles are covered under health insurance by occupation.