What Claude (Anthropic) with web search answered for payroll software (freelancers) on 2026-09-24

Claude (Anthropic) with web search claude-opus-5 asked 2026-09-24

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. S-corp mentioned
   This only becomes a real need once you've elected S-corp status and owe yourself a reasonable W-2 salary.
2. Gusto mentioned
   Gusto - the default pick.
3. OnPay mentioned
   OnPay - flat ~$40/mo + $6/person with no feature tiers, so a one-person S-corp gets the same product a 50-person company does.
4. Collective mentioned
   Collective - not software, a service: payroll + bookkeeping + S-corp tax filing bundled for a few hundred a month, built specifically for solo freelancers who've made the S-corp election.
5. Square mentioned
   Square Payroll - cheapest credible option (~$35/mo + $6), makes sense if you already take payments through Square.
6. Gusto Contractor mentioned
   Gusto Contractor Only - $6/contractor/month with the base fee currently waived in a promo.
7. Gusto Contractor Only mentioned
   Gusto Contractor Only - $6/contractor/month with the base fee currently waived in a promo.
8. Deel mentioned
   Deel - the one to use for international freelancers.
9. Wise compared
   Wise Business batch payments - if you're paying overseas freelancers who handle their own compliance, this is dramatically cheaper than Deel for the actual money movement.
10. Wise Business compared
    Wise Business batch payments - if you're paying overseas freelancers who handle their own compliance, this is dramatically cheaper than Deel for the actual money movement.
11. Wave mentioned
    Wave - free/near-free and fine if you're paying one or two people occasionally and don't need automated filings.
12. Airwallex mentioned
    - Airwallex - 10 Best Payroll Software Providers for Small Businesses in 2026 (https://www.airwallex.com/en-us/blog/best-payroll-software)

Sources the engine cited

The answer, as recorded

Short version up front: "payroll software" means two different things for freelancers, and the right answer depends on which one you are. ## If you're the freelancer paying yourself If you're a sole proprietor or default single-member LLC, **you don't need payroll software at all** - you take an owner's draw, and payroll would just be an expense with no tax benefit. This only becomes a real need once you've elected S-corp status and owe yourself a reasonable W-2 salary. 1. **Gusto** - the default pick. Its Simple plan (~$49/mo + $6/person) runs an owner-only payroll on autopilot, files your 941s/940/W-2, and handles multi-state if you move. Best UI in the category and it also pays contractors from the same account. 2. **OnPay** - flat ~$40/mo + $6/person with no feature tiers, so a one-person S-corp gets the same product a 50-person company does. Cheaper than Gusto at scale-of-one and the support is genuinely good. 3. **Collective** - not software, a service: payroll + bookkeeping + S-corp tax filing bundled for a few hundred a month, built specifically for solo freelancers who've made the S-corp election. Worth it if you'd rather not think about reasonable-salary math at all. 4. **QuickBooks Payroll** - only because your books are probably already there. Don't switch to it; use it if you're already on QBO. 5. **Square Payroll** - cheapest credible option (~$35/mo + $6), makes sense if you already take payments through Square. ## If you're hiring freelancers and need to pay them 1. **Gusto Contractor Only** - $6/contractor/month with the base fee currently waived in a promo. Collects W-9s at onboarding and auto-e-files 1099-NECs for anyone over $600. 2. **Square Payroll contractor-only** - $0 base + ~$6/contractor, same 1099 automation, less HR cruft. The price winner for US-only contractors. 3. **Deel** - the one to use for international freelancers. Localized contracts and tax-form collection across 150+ countries; that compliance layer is the whole reason to pay its premium (~$49/contractor). 4. **Wise Business batch payments** - if you're paying overseas freelancers who handle their own compliance, this is dramatically cheaper than Deel for the actual money movement. 5. **Wave** - free/near-free and fine if you're paying one or two people occasionally and don't need automated filings. One caveat: contractor-plan pricing in this space changes constantly and several of these numbers are promotional, so confirm on the provider's own pricing page before committing. Sources: - [Gusto - Best Contractor Payroll Services and Software](https://gusto.com/resources/guides/best-contractor-payroll-software) - [Gusto - Pricing](https://gusto.com/product/pricing) - [People Managing People - 10 Best Payroll Software for Contractors in 2026](https://peoplemanagingpeople.com/tools/best-payroll-software-for-contractors/) - [Wise - 11 Best Contractor Payroll Software for US Employers in 2026](https://wise.com/us/blog/batchtransfer-contractor-payroll-software) - [Collective - S Corp Reasonable Salary: A Guide To Paying Yourself](https://www.collective.com/blog/money-management/freelancers-guide-to-paying-yourself-a-salary-from-an-s-corporation) - [Gusto - How To Pay Yourself as a Single-Member LLC](https://gusto.com/resources/articles/payroll/pay-myself-owner-single-member-llc) - [Airwallex - 10 Best Payroll Software Providers for Small Businesses in 2026](https://www.airwallex.com/en-us/blog/best-payroll-software)

Markdown edition · the question page, with every recording · Answer Watch · AEO Watch

Answer Watch records what one AI answer engine said on one date, nothing more. Each page names the engine and the model, carries the date the question was asked, and lists the brands that appeared in the answer in the order the engine gave them, with the sources it cited. It is a measurement, not a ranking, not a recommendation and not a claim about the world. Brands that did not appear in an answer are not named on any public page. Coverage: Claude (Anthropic) with web search. Other engines not included.