# Contractor payments for small business buyers: what AI models recommend, September 2026

Finance AI Recommendation Index, September 2026 Edition. Asked as "contractor payments and 1099 platform" and as "freelancer payout software", six framings each, to twelve models with search on, on behalf of a small B2B company. Page: https://finance-ai-index.com/spend/contractor-payments/smb/

**Standing:** Gusto leads with 59% of first choices; verdict clear leader. 46 first choices across the direct, paraphrase, budget and scale prompts.

## First-choice share

| # | Product | Share | Negative rate | Labels |
|---|---|---|---|---|
| 1 | Gusto | 59% | 2% | 55 |
| 2 | Square Payroll | 11% | 19% | 16 |
| 3 | Wingspan | 4% | 0% | 12 |
| 4 | BILL | 4% | 17% | 12 |
| 5 | Wise Business | 2% | 9% | 23 |
| 6 | Deel | 0% | 9% | 45 |
| 7 | Remote | 0% | 5% | 21 |
| 8 | Rippling | 0% | 18% | 17 |
| 9 | Melio | 0% | 15% | 13 |
| 10 | Tipalti | 0% | 23% | 13 |
| 11 | PayPal | 0% | 90% | 10 |

## Each model's first choice on the direct prompt

- Claude Haiku 4.5: Gusto; alternatives QuickBooks, SurePayroll
- GPT-5.4 mini: Gusto; alternatives BILL, Deel, QuickBooks Contractor Payments, QuickBooks Payroll
- Gemini 3.5 Flash: Gusto; alternatives Deel, Melio, Square Payroll, Wingspan
- Perplexity Sonar: Gusto; alternatives ADP RUN, Deel, QuickBooks Contractor Payments, QuickBooks Payroll
- Grok 4.1 Fast: Gusto; alternatives BILL, Deel, QuickBooks Online, Rippling
- Mistral Small: Gusto, Wingspan; alternatives Deel, QuickBooks Contractor Payments, Tipalti
- DeepSeek V4 Flash: Gusto; alternatives Deel, QuickBooks Contractor Payments
- Llama 4 Maverick: no first choice
- Qwen 3.7 Flash: Gusto; alternatives Deel, Rippling, Wingspan
- Kimi K2: Gusto; alternatives BILL, Deel, Melio
- GLM 4.7 FlashX: Routable; alternatives Deel, Gusto, Tipalti
- MiniMax M2.5: Gusto; alternatives Deel, Remote, Wingspan, Worksuite

## Sources the answers cite

67 of 72 answers came back with a source list, from 12 of 12 models. Sites named in the most answers:

- worksuite.com: 40 answers, 43 citations
- learn.g2.com: 34 answers, 35 citations
- remote.com: 31 answers, 32 citations
- contractor-of-record.com: 30 answers, 30 citations
- wingspan.app: 29 answers, 33 citations
- gusto.com: 28 answers, 46 citations
- relayfi.com: 18 answers, 18 citations
- wise.com: 16 answers, 23 citations

Pages named in the most answers:

- https://worksuite.com/resources/insights/best-contractor-payment-software (40 answers)
- https://learn.g2.com/best-contractor-payment-software (34 answers)
- https://remote.com/blog/payroll/best-contractor-payment-tools (30 answers)
- https://contractor-of-record.com/software/contractor-payouts (29 answers)
- https://wingspan.app/articles/best-contractor-payroll-services (23 answers)
- https://relayfi.com/blog/best-1099-software-small-businesses-guide (18 answers)
- https://guideflow.com/blog/contractor-payment-software (16 answers)
- https://riseworks.io/blog/best-payroll-providers-for-automated-contractor-payments-and-1099s (15 answers)
- https://gusto.com/resources/guides/best-contractor-payroll-software (14 answers)
- https://bolto.com/blog/best-1099-software-for-small-business (12 answers)

## Warned against

- PayPal: 9 of 10 labels negative. "Small businesses should be cautious about PayPal, traditional bank wires, and any platform that does not explicitly address compliance" (Mistral Small, negative prompt)
- Venmo: 7 of 7 labels negative. "Consumer payment apps like PayPal and Venmo may seem convenient for small jobs, but they are often not ideal for growing businesses." (Claude Haiku 4.5, negative prompt)
- Cash App: 5 of 5 labels negative. "Peer-to-Peer (P2P) Consumer Apps (e.g., Venmo, Cash App, Zelle, Personal PayPal) ... Why to avoid them" (Gemini 3.5 Flash, negative prompt)
- Stripe: 4 of 5 labels negative. "Frequent reports of holding funds in "reserves" for 6+ months, account freezes, and delays in payouts" (Grok 4.1 Fast, negative prompt)

## Record

- Method: https://finance-ai-index.com/methodology/
- Raw judge labels and full responses: https://finance-ai-index.com/data/
- License: CC BY 4.0. Cite as Finance AI Recommendation Index, September 2026 Edition, finance-ai-index.com.