The moments that matter
Tech careers have more coverage transitions than most: layoffs, the gap before a new job's benefits start, leaving to found a company, or switching to contract work. Each of these is a qualifying event. Losing job-based coverage opens a 60-day Special Enrollment Period to buy an individual plan, so you do not have to wait for Open Enrollment.
| Situation | Options to compare |
|---|---|
| Laid off | COBRA (same plan, full cost plus up to 2%); individual plan; a spouse's plan |
| Starting a new job soon | COBRA for the gap, or an individual plan that starts the 1st of next month |
| Founding a startup | Individual plans for founders; ICHRA or a small-group plan once you hire |
| Contracting (1099) | Individual plan plus the self-employed health insurance deduction |
How equity and severance affect 2027 subsidies
Premium tax credits for 2027 depend on your full-year household income (modified AGI), not your salary at the time you apply. The credit stops at 400% of the poverty level: $63,840 for one person or $132,000 for a family of four.
- RSUs are taxed as wages when they vest, so vests later in the year count.
- NSO exercises create ordinary income on the spread; ISO exercises generally do not for regular tax (watch AMT).
- Severance and stock sales count toward income in the year received.
- Founders and contractors use net self-employment income after business expenses.
COBRA or an individual plan?
COBRA keeps your exact plan and network, and any deductible you have already met carries over. That is valuable mid-year or mid-treatment. But you pay the employer's share as well: family COBRA often costs well over $2,000 a month.
A full-price individual benchmark Silver plan averages $795/month for a 45-year-old and $2,434/month for a family of four with 45-year-old parents in 2027 (national averages from KFF's $704 benchmark for age 40). If your income for the year will land under 400% FPL, for example after a layoff early in the year, a subsidized plan can cost far less than COBRA.
Remote work and networks
Individual plans are local: networks are built around your county, and many are EPOs with no out-of-network coverage except emergencies. If you work remotely while traveling or split time between states, check how the plan covers routine care away from home, or look at plans with national networks where they are offered.
Founders: from one person to a team
- Solo founder: buy an individual plan; if you have net self-employment income, deduct premiums.
- First hires: an ICHRA lets you set a fixed monthly allowance and lets each employee pick their own plan, which suits distributed teams.
- Growing team: a small-group plan becomes practical once you have enough enrolled employees in one area.
- HSA: for 2027 you can contribute up to $4,500 (self-only) or $9,000 (family) with an HSA-eligible plan.
Frequently Asked Questions
Sources: IRS Rev. Proc. 2026-26 (2027 premium tax credit table) and Rev. Proc. 2026-24 (2027 HSA limits); 2026 HHS poverty guidelines; KFF, 2027 average benchmark premiums. Premium figures are national averages for planning, not quotes. Tax rules depend on your situation; confirm with your tax advisor.