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You quit the job, got the LLC, built the client roster — and then open enrollment showed up and nobody was there to walk you through it. No employer already vetted a handful of plans and highlighted the best options during a benefits meeting. No HR inbox to ask “wait, what’s a deductible again?” It’s just you, a login to a state or federal marketplace, and a wall of plan names that all sound the same.
This is one of the real costs of going solo that doesn’t show up on a spreadsheet: the time and stress of shopping for health insurance alone. You’re comparing premiums, deductibles, networks, and subsidy eligibility while also trying to run a business, and one wrong click during open enrollment can lock you into a plan that doesn’t cover your doctor or your medication.
The tools below won’t replace a conversation with a licensed agent when your situation is complicated, but they do the same job a benefits broker used to do at a bigger company: narrow hundreds of plans down to a handful worth comparing, based on your income, household, and health needs. Most are free to you because they earn a commission from insurers when you enroll — the same way a traditional broker gets paid, just without the office visit.
The best AI health insurance and benefits tools for solopreneurs
These five tools cover the two main paths solopreneurs actually take: shopping the ACA marketplace with help, or building something closer to small-group coverage when you work with contractors. One is a supplement, not a substitute, for either.
Stride Health
Stride Health is a free plan-shopping platform built for independent workers — it started out serving gig and delivery drivers and has expanded into a general marketplace tool for freelancers and solopreneurs. Its standout feature is a recommendation engine that scans marketplace plans in your area and ranks them based on your income, medications, and preferred doctors, rather than just showing you every option sorted by price. Stride is an official Healthcare.gov enrollment partner, so you’re seeing the same ACA plans and pricing you’d find on the government site, just with guided comparison layered on top. It’s free to use, since Stride is paid by insurers when you enroll through the platform.
HealthSherpa
HealthSherpa is one of the largest ACA enrollment platforms in the country and functions as a direct, faster front end to the federal marketplace. Its plan-matching tool asks about your household, income, and any doctors or prescriptions you want to keep, then filters the marketplace catalog down to plans that fit — a process HealthSherpa says takes a few minutes instead of the longer slog through Healthcare.gov directly. It also has licensed agents on standby if you want a person to double-check the recommendation. HealthSherpa is free for consumers; like Stride, it earns its revenue from insurance carriers when you enroll.
Catch
Catch is a benefits platform built specifically for freelancers and the self-employed, covering health insurance, retirement contributions, and tax withholding in one dashboard — useful if you want your coverage shopping and your quarterly tax planning to live in the same place. On the health side, Catch is also an official Healthcare.gov partner: you enter your household and income details and it automatically applies available premium tax credits to the plans it shows you, so the price you see reflects any subsidy you likely qualify for. Joining Catch is free, and free licensed-agent support is included if you want help finalizing a plan.
Gravie
Gravie takes a different approach: instead of shopping the individual ACA marketplace, it builds level-funded health plans and ICHRA (Individual Coverage Health Reimbursement Arrangement) programs — the small-business-style setup that lets an employer hand workers a fixed budget to buy their own coverage. This matters for solopreneurs who’ve grown into hiring a contractor or two, or who operate as a C-corp, since ICHRA can let you reimburse health premiums tax-free through your business. One important caveat: sole proprietors and S-corp owners who own more than 2% of the company typically don’t qualify as “employees” for ICHRA purposes, so check your business structure against current IRS rules — or talk to Gravie directly — before assuming this path works for you. Gravie doesn’t publish flat consumer pricing, since costs depend on the plan design your business sets up.
GoodRx
GoodRx isn’t health insurance and won’t replace a plan — it’s a free prescription discount tool worth stacking on top of whatever coverage you land on. You search your medication, and GoodRx shows negotiated cash prices at nearby pharmacies, sometimes cheaper than your insurance copay, especially for common generics. It’s free to use with no signup required for the basic coupons, and GoodRx makes money from a referral fee paid by the pharmacy benefit manager, not from you. Keep it in your back pocket even after you’ve chosen a plan through one of the tools above.
Which one should you choose?
If you’re shopping the ACA marketplace as an individual, start with Stride Health, HealthSherpa, or Catch — try two of them, since matching algorithms and available agent support differ slightly, and cross-checking gives you a sanity check on the recommendation. If you’re past pure solopreneur status and working regularly with contractors or run a C-corp, Gravie’s ICHRA route is worth a serious look as a small-group-style alternative. And no matter which plan you land on, run your prescriptions through GoodRx before you assume your insurance copay is the best price available.
Health insurance is only one piece of the financial infrastructure a solopreneur has to build without an HR department; the other pieces — estimated taxes, bookkeeping, and eventually payroll if you bring on help — deserve the same kind of tooling. We’ve covered AI-powered finance and tax tools for the quarterly-payment side of things, and if you ever cross the line into hiring, our roundup of AI payroll tools covers what changes once you’re the one issuing paychecks.
If you’d rather have this kind of comparison land in your inbox before you need it, our newsletter, The Solo Stack, rounds up tools like these for solopreneurs a couple of times a month.
Frequently asked questions
Can I deduct health insurance premiums as a self-employed person?
In many cases, yes — the self-employed health insurance deduction lets eligible business owners deduct premiums paid for themselves and their families, which lowers your taxable income even if you don’t itemize. Eligibility involves factors like whether you have net profit from your business and whether you’re eligible for an employer-subsidized plan through a spouse, so confirm your specific situation with a tax professional or current IRS guidance rather than assuming it applies automatically.
When is ACA open enrollment?
Open enrollment for ACA marketplace plans typically runs in the fall through mid-January for coverage starting the following year, but exact dates and any special enrollment windows can shift, and some states running their own exchanges set different deadlines. Check healthcare.gov or your state’s marketplace site directly for the current enrollment window before you plan around a specific date.
Do these tools cost anything?
Stride Health, HealthSherpa, and Catch are all free for consumers to use for ACA plan shopping — they’re paid by insurance carriers when you enroll, similar to how a traditional insurance broker earns a commission. GoodRx is free with no membership required for basic discount coupons. Gravie’s pricing depends on the plan or ICHRA structure your business sets up, so you’d need to request details directly.
Are there alternatives to ACA marketplace plans?
Yes. Options solopreneurs sometimes use alongside or instead of ACA marketplace plans include short-term or supplemental health plans (which typically don’t cover pre-existing conditions and aren’t ACA-compliant), health sharing ministries (not insurance, and coverage isn’t guaranteed the way an insurance contract works), COBRA continuation from a former job for a limited time, coverage through a spouse’s employer plan, and ICHRA-style arrangements if your business structure qualifies. Each comes with real tradeoffs, so weigh them carefully rather than picking based on price alone.
Is this personalized insurance advice?
No. We’re not licensed insurance agents or brokers, and nothing in this article is personalized insurance, tax, or legal advice — it’s a starting point for researching tools that can help you shop more efficiently. Health insurance decisions depend on your income, health needs, family situation, and state, so verify plan details, subsidy eligibility, and enrollment rules directly with healthcare.gov, your state marketplace, or a licensed agent before you enroll.