What Claude (Anthropic) with web search answered for payroll software (freelancers) on 2026-10-05

Claude (Anthropic) with web search claude-opus-5 asked 2026-10-05

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. Patriot mentioned
   Patriot Software - ~$37/mo + $5 per worker paid.
2. Gusto mentioned
   Gusto - $49/mo + $6/person.
3. Wave mentioned
   Wave Payroll - Best if you're mainly paying contractors, not yourself, and you already use Wave for invoicing/bookkeeping.
4. Square mentioned
   Square Payroll - ~$35/mo + $6/person, and it has a contractor-only plan at per-person pricing with no monthly base - the cheapest way to formalize 1099 payments.
5. Lettuce mentioned
   Lettuce - Niche but genuinely interesting: it's a bundled bookkeeping + payroll + S-corp setup service aimed specifically at businesses-of-one.
6. Deel mentioned
   Deel - Only if you're subcontracting work to people in other countries.
7. Wise mentioned
   For plain cross-border transfers with no compliance layer, Wise is far cheaper (often under 1%).

Sources the engine cited

The answer, as recorded

## First, the honest answer: most freelancers don't need payroll software If you're a sole proprietor or single-member LLC, **you can't put yourself on payroll.** You pay yourself with owner's draws - transfer money from the business account to your personal account. Nothing is withheld, no W-2, no filings. You handle taxes through quarterly estimated payments. Payroll software would just be a monthly fee for a job that doesn't exist. ([SurePayroll](https://www.surepayroll.com/resources/article/how-to-pay-yourself-in-an-llc), [NerdWallet](https://www.nerdwallet.com/business/learn/how-to-pay-yourself-as-an-llc)) You actually need payroll in three cases: you've elected **S-corp** taxation (now you must pay yourself a reasonable W-2 salary), you've **hired someone**, or you're **paying subcontractors** and want 1099s handled. Here's who I'd use, in order: **1. Patriot Software** - ~$37/mo + $5 per worker paid. My default pick for a solo S-corp owner. Full-service (files your federal/state payroll taxes), and critically, it only charges per worker *actually paid* that month - good if you run payroll quarterly rather than biweekly. Cheapest real full-service option. ([pricing comparison](https://www.patriotsoftware.com/payroll/compare/patriot-software-vs-gusto/)) **2. Gusto** - $49/mo + $6/person. More expensive, but the best-built product of the group: clean interface, automatic filings, handles multi-state, and it'll sell you health insurance and a solo 401(k) if you want them. Worth the extra ~$13/mo if you'd rather never think about it. ([Gusto](https://gusto.com/resources/guides/best-payroll-software-one-employee)) **3. Wave Payroll** - Best if you're mainly paying *contractors*, not yourself, and you already use Wave for invoicing/bookkeeping. Direct deposit plus W-2 and 1099 generation, and the bookkeeping side is free. ([Wave](https://www.waveapps.com/payroll)) **4. Square Payroll** - ~$35/mo + $6/person, and it has a **contractor-only plan at per-person pricing with no monthly base** - the cheapest way to formalize 1099 payments. Obvious choice if you already take payments through Square. ([comparison](https://www.beltstack.com/payroll/compare/square-payroll-vs-gusto)) **5. Lettuce** - Niche but genuinely interesting: it's a bundled bookkeeping + payroll + S-corp setup service aimed specifically at businesses-of-one. Costs more than the above, but it does the S-corp election and the reasonable-salary math for you. Consider it if you're *thinking about* S-corp and don't want to hire a CPA separately. ([Lettuce](https://lettuce.co/resources/best-payroll-software-for-solopreneurs-more-take-home-pay)) **6. Deel** - Only if you're subcontracting work to people in other countries. Handles contracts, W-8BENs, local compliance, and payments in 150+ countries. For plain cross-border transfers with no compliance layer, **Wise** is far cheaper (often under 1%). ([Deel](https://www.deel.com/blog/best-global-payment-tools-for-contractors/), [Wise/Deel breakdown](https://www.kemecon.com/blog/paying-freelancers-abroad-in-2026-a-practical-breakdown-of-wise-payoneer-and-deel)) **My recommendation:** if you're a regular freelancer, skip all of this - use a bookkeeping tool and pay quarterly estimates. If you're netting enough that S-corp makes sense (very roughly $80k+ of profit, worth a conversation with a CPA), go **Patriot** for cost or **Gusto** for polish. Sources: - https://www.surepayroll.com/resources/article/how-to-pay-yourself-in-an-llc - https://www.nerdwallet.com/business/learn/how-to-pay-yourself-as-an-llc - https://www.patriotsoftware.com/payroll/compare/patriot-software-vs-gusto/ - https://gusto.com/resources/guides/best-payroll-software-one-employee - https://www.waveapps.com/payroll - https://www.beltstack.com/payroll/compare/square-payroll-vs-gusto - https://lettuce.co/resources/best-payroll-software-for-solopreneurs-more-take-home-pay - https://www.deel.com/blog/best-global-payment-tools-for-contractors/ - https://www.kemecon.com/blog/paying-freelancers-abroad-in-2026-a-practical-breakdown-of-wise-payoneer-and-deel

Near this answer

The same question, recorded on other dates: 2026-10-03, 2026-10-01, 2026-09-26, 2026-09-24, 2026-09-22, 2026-09-20, 2026-09-16, 2026-09-14, 2026-09-12, 2026-09-10, 2026-09-07.

payroll software, asked for other audiences: small businesses (asked 2026-10-05), nonprofits (asked 2026-10-05).

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

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