You left corporate. Your benefits didn't follow.

Your Health Coverage Is Now a $20,000+ Business Decision

When you went fractional, you lost more than a paycheck. Employer health coverage, HSA contributions, disability insurance — all gone. Covered by Keith helps fractional executives and independent consultants replace that safety net with private health plans that offer better doctor networks and better rates.

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$20,000–$30,000

Annual value of corporate benefits the average fractional exec lost

Source: Bureau of Labor Statistics

14%+

Proposed ACA premium increase for 2027

Source: KFF

58%

Average premium increase after enhanced subsidies expired

Source: KFF

What You Lost When You Went Fractional

The corporate benefits package was worth more than most people realize. Here's what walked out the door with your W-2.

Health Coverage

Employer paid ~$7,000–$15,000/year

401k Match

Typically 3–6% of salary

HSA/FSA Contributions

Often $1,000–$3,000/year

Disability Insurance

Short + long term coverage

Life Insurance

Often 1–2x salary, free

The Fractional Exec's Coverage Strategy

01

Audit What You Lost

Get a clear breakdown of the benefits package you left behind and what it costs to replace.

02

Build Your Private Coverage Portfolio

Private health plan + HSA + supplemental coverage — structured for your income and tax situation.

03

Optimize for Tax Efficiency

Self-employed health insurance deduction, HSA triple tax advantage, S-corp premium structuring.

Private Plans vs. ACA Marketplace

FeatureACA MarketplacePrivate Health Plans
Doctor NetworksLimited, narrow networksBroader, preferred provider networks
Monthly PremiumRising 14%+ in 2027Often lower with better coverage
HSA EligibilityOnly specific metal-tier plansMany HDHP options available
Tax EfficiencyLimited deduction optionsFull self-employed deduction + HSA
Wait TimesLonger for specialistsPriority access, shorter waits

The HSA Advantage for High Earners

An HSA is the only account with a triple tax advantage: contributions are tax-deductible, growth is tax-free, and withdrawals are tax-free for qualified medical expenses. After age 65, HSA funds work like a traditional IRA for non-medical expenses.

$4,400

2026 individual contribution limit

$8,350

2026 family contribution limit

$1,500–$2,500

Annual tax savings when maxed

For high-earning fractional execs, maxing an HSA can save $1,500–$2,500/year in taxes while building a stealth retirement account.

Don't Wait for Open Enrollment

The 2027 rate increases are coming. Find out if a private plan can save you money before November 1st.

Covered by Keith — Independent Health Insurance Broker

Personalized health coverage guidance for self-employed professionals, real estate agents, consultants, and 1099 earners.

Independent Licensed Health Insurance Broker

Keith Cheverie is an independent licensed health insurance producer/broker. Coverage availability, eligibility, benefits, provider networks, premiums, and out-of-pocket costs vary by state, carrier, plan, and applicant. Not all products are available in all states. This website is not affiliated with or endorsed by the U.S. government, Medicare, Medicaid, or the Health Insurance Marketplace.

Licensed in multiple states. License information is available upon request.

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