What Claude (Anthropic) with web search answered for payroll software (freelancers) on 2026-09-07

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-07

Coverage: Claude (Anthropic) with web search. Other engines not included.

The question asked, verbatim: best payroll software for freelancers

Brands named, in the order the engine gave

1. Collective compared
   (selfemployed.com (https://www.selfemployed.com/payroll-options-for-self-employed-business-owners/), Collective (https://www.collective.com/blog/money-management/payroll-solutions-for-solopreneurs-a-comparison-guide))
2. Square mentioned
   Square Payroll - the cheapest real option: $0 base, $6 per contractor per month for contractor-only businesses.
3. Gusto mentioned
   (Gusto's Square pricing guide (https://gusto.com/resources/guides/switch-payroll-providers/square-pricing))
4. Deel mentioned
   Deel - only if your subcontractors are overseas.
5. Airwallex mentioned
   (Airwallex (https://www.airwallex.com/en-us/blog/best-payroll-software))
6. Patriot mentioned
   Patriot Software - the budget pick: Full Service at ~$37/mo + $5/employee, Basic at ~$17 + $4 if you're willing to file the taxes yourself.
7. OnPay mentioned
   OnPay - $49 base + $6 per worker, and it only charges the $6 in months you actually paid that person.
8. Wave recommended
   Wave Payroll gets recommended for freelancers a lot, and it's cheap if you're already using Wave's free accounting - but it only offers full tax filing in a subset of states;
9. ADP mentioned
   (Research.com (https://research.com/software/reviews/wave-payroll)) ADP and Paychex will both sell you a one-person plan and both are solid enterprise products, but pricing is quote-based and the support model isn't aimed at you.
10. Paychex mentioned
    (Research.com (https://research.com/software/reviews/wave-payroll)) ADP and Paychex will both sell you a one-person plan and both are solid enterprise products, but pricing is quote-based and the support model isn't aimed at you.

Sources the engine cited

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The answer, as recorded

## First, the honest caveat If you're a sole proprietor or single-member LLC, **you probably don't need payroll software at all.** You pay yourself with an owner's draw - just move money from the business account to your personal one - and cover taxes with quarterly estimateds. Payroll actually becomes necessary in two cases: you've elected **S-corp** taxation (the IRS then requires you to pay yourself a "reasonable salary" through real payroll), or you're **paying subcontractors** and want the 1099s handled for you. ([selfemployed.com](https://www.selfemployed.com/payroll-options-for-self-employed-business-owners/), [Collective](https://www.collective.com/blog/money-management/payroll-solutions-for-solopreneurs-a-comparison-guide)) Here's what I'd actually pick, for each case. ## If you're paying subcontractors (1099s) **1. Square Payroll** - the cheapest real option: $0 base, $6 per contractor per month for contractor-only businesses. No monthly subscription at all in months you don't pay anyone. If cost is the deciding factor and you just need 1099-NECs filed, this is the answer. ([Gusto's Square pricing guide](https://gusto.com/resources/guides/switch-payroll-providers/square-pricing)) **2. Gusto (Contractor Only plan)** - $35/mo + $6/contractor, though the base fee is currently waived on a promo. Costs more than Square but the onboarding, W-9 collection, and year-end filing are noticeably smoother, and you can grow into real employee payroll without switching tools. ([gustopricing.com](https://gustopricing.com/contractor-plan), [Gusto pricing](https://gusto.com/product/pricing)) **3. Deel** - only if your subcontractors are overseas. It localizes contracts and collects the right tax forms across 150+ countries, which is the part that actually goes wrong with international freelancers. Overkill and overpriced for a domestic-only setup. ([Airwallex](https://www.airwallex.com/en-us/blog/best-payroll-software)) ## If you've S-corp'd yourself and need to run your own salary **1. Gusto** - my default recommendation. It's built with owner-employees and S-corp compliance in mind, files federal/state/local automatically, and handles the W-2 you'll issue yourself. Simple plan runs about $49/mo + $6/person. ([Gusto pricing](https://gusto.com/product/pricing)) **2. Patriot Software** - the budget pick: Full Service at ~$37/mo + $5/employee, Basic at ~$17 + $4 if you're willing to file the taxes yourself. Less polished than Gusto, but for one predictable salary paid twice a month, polish doesn't buy you much. ([eLearning Industry](https://elearningindustry.com/patriot-payroll-pricing), [cheapestpayrollservice.com](https://cheapestpayrollservice.com/cheapest-patriot-plan)) **3. OnPay** - $49 base + $6 per worker, and it only charges the $6 in months you actually paid that person. Genuinely good S-corp documentation and support; a fair alternative if Gusto's interface doesn't click for you. ([OnPay](https://onpay.com/payroll/software/industries/s-corp-payroll/)) **4. Collective** - not software, a service: bookkeeping, payroll, and S-corp tax filing bundled for solopreneurs. Costs several times the others, but if "reasonable salary" and quarterly filings are the thing you keep procrastinating on, paying someone to own it is a legitimate call. ([Collective](https://www.collective.com/blog/money-management/payroll-solutions-for-solopreneurs-a-comparison-guide)) ## Ones I'd skip **Wave Payroll** gets recommended for freelancers a lot, and it's cheap if you're already using Wave's free accounting - but it only offers full tax filing in a subset of states; everywhere else you file yourself while still paying a base fee. Check your state before committing. ([Research.com](https://research.com/software/reviews/wave-payroll)) **ADP** and **Paychex** will both sell you a one-person plan and both are solid enterprise products, but pricing is quote-based and the support model isn't aimed at you. ([ADP](https://www.adp.com/what-we-offer/payroll/payroll-for-one-employee.aspx)) **Short version:** paying subs → Square Payroll. S-corp salary → Gusto, or Patriot if you're cost-sensitive. Plain sole prop → don't buy payroll software; open a separate business checking account and set aside 25-30% for quarterlies. Sources: - [selfemployed.com - payroll options for self-employed](https://www.selfemployed.com/payroll-options-for-self-employed-business-owners/) - [Collective - payroll solutions for solopreneurs](https://www.collective.com/blog/money-management/payroll-solutions-for-solopreneurs-a-comparison-guide) - [Gusto - Square Payroll pricing 2026](https://gusto.com/resources/guides/switch-payroll-providers/square-pricing) - [Gusto - pricing](https://gusto.com/product/pricing) - [GustoPricing.com - Contractor Only plan](https://gustopricing.com/contractor-plan) - [Airwallex - best payroll software](https://www.airwallex.com/en-us/blog/best-payroll-software) - [eLearning Industry - Patriot pricing](https://elearningindustry.com/patriot-payroll-pricing) - [cheapestpayrollservice.com - cheapest Patriot plan](https://cheapestpayrollservice.com/cheapest-patriot-plan) - [OnPay - S-corp payroll](https://onpay.com/payroll/software/industries/s-corp-payroll/) - [Research.com - Wave Payroll review](https://research.com/software/reviews/wave-payroll) - [ADP - payroll for one employee](https://www.adp.com/what-we-offer/payroll/payroll-for-one-employee.aspx) One note on the pricing above: figures come from third-party roundups and move around (sources disagreed on Wave in particular, and Gusto's waived base fee is promotional). Confirm current numbers on each vendor's own pricing page before you sign up.

Near this answer

The same question, recorded on other dates: 2026-10-23, 2026-10-21, 2026-10-18, 2026-10-15, 2026-10-13, 2026-10-10, 2026-10-08, 2026-10-06, 2026-10-05, 2026-10-03, 2026-10-01, 2026-09-26.

payroll software, asked for other audiences: small businesses (asked 2026-10-23), nonprofits (asked 2026-10-21).

Other categories with a recorded answer: accounting software, accounts payable automation, audit management software, bookkeeping services.

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