# Contractor payments: what AI models recommend, September 2026

Gane 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 mid-market B2B company. Page: https://www.gane.ai/index/finance/spend/contractor-payments/2026-09

This is the permanent record of the September 2026 Edition, published September 17, 2026 and superseded since. The current standing: https://www.gane.ai/index/finance/spend/contractor-payments/index.md

**Standing:** Deel leads with 27% of first choices; verdict contested. 44 first choices across the direct, paraphrase, budget and scale prompts.

## First-choice share

| Rank | Product | Share | Negative rate | Labels |
|---|---|---|---|---|
| 1 | [Deel](https://www.gane.ai/index/finance/vendors/deel/index.md) | 27% | 4% | 49 |
| 2 | [Square Payroll](https://www.gane.ai/index/finance/vendors/square-payroll/index.md) | 14% | 0% | 12 |
| 3 | [Tipalti](https://www.gane.ai/index/finance/vendors/tipalti/index.md) | 7% | 4% | 24 |
| 4 | [Rippling](https://www.gane.ai/index/finance/vendors/rippling/index.md) | 7% | 11% | 27 |
| 5 | [Trolley](https://www.gane.ai/index/finance/vendors/trolley/index.md) | 7% | 0% | 12 |
| 6 | [Remote](https://www.gane.ai/index/finance/vendors/remote/index.md) | 5% | 0% | 28 |
| 7 | [Gusto](https://www.gane.ai/index/finance/vendors/gusto/index.md) | 5% | 11% | 37 |
| 8 | [Routable](https://www.gane.ai/index/finance/vendors/routable/index.md) | 5% | 0% | 11 |
| 10 | [Papaya Global](https://www.gane.ai/index/finance/vendors/papaya-global/index.md) | 2% | 5% | 19 |
| 11 | [Worksuite](https://www.gane.ai/index/finance/vendors/worksuite/index.md) | 2% | 0% | 17 |
| 12 | [BILL](https://www.gane.ai/index/finance/vendors/bill/index.md) | 2% | 20% | 15 |
| 19 | [Wingspan](https://www.gane.ai/index/finance/vendors/wingspan/index.md) | 0% | 0% | 17 |

Rank is by share of first choices among all 77 products named; products with the same share are tied, and the order among them carries no meaning. The table lists those with at least 10 labels.

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

- Claude Haiku 4.5: Worksuite; alternatives Deel, Tipalti
- GPT-5.4 mini: Deel; alternatives Gusto, Tipalti
- Gemini 3.5 Flash: Rippling; alternatives Deel, Remote, Tipalti, Wingspan
- Perplexity Sonar: Deel; alternatives Remote, Tipalti
- Grok 4.20: Rippling; alternatives BILL, Deel, Gusto, Routable
- Mistral Small: Routable; alternatives Deel, Tipalti, Wingspan
- DeepSeek V4 Flash: Tipalti; alternatives BILL, Deel, Routable, Wingspan
- Llama 4 Maverick: Routable; alternatives BILL, Wingspan
- Qwen 3.7 Flash: Tipalti; alternatives Deel, Routable
- Kimi K2: BILL, Gusto; alternatives Routable, Tipalti, Wingspan
- GLM 4.7 FlashX: Deel, Remote; alternatives Gusto, Oyster, Routable
- MiniMax M2.5: Deel; alternatives Gusto, Tipalti

## 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: 42 answers, 47 citations
- remote.com: 39 answers, 40 citations
- wingspan.app: 33 answers, 40 citations
- contractor-of-record.com: 33 answers, 33 citations
- learn.g2.com: 28 answers, 31 citations
- deel.com: 23 answers, 37 citations
- guideflow.com: 23 answers, 24 citations
- papayaglobal.com: 20 answers, 24 citations

Pages named in the most answers:

- https://worksuite.com/resources/insights/best-contractor-payment-software (40 answers)
- https://remote.com/blog/payroll/best-contractor-payment-tools (37 answers)
- https://wingspan.app/articles/best-contractor-payroll-services (33 answers)
- https://contractor-of-record.com/software/contractor-payouts (33 answers)
- https://learn.g2.com/best-contractor-payment-software (28 answers)
- https://guideflow.com/blog/contractor-payment-software (20 answers)
- https://riseworks.io/blog/best-payroll-providers-for-automated-contractor-payments-and-1099s (13 answers)
- https://routable.com/resources/best-1099-automation-platforms-high-volume-businesses (13 answers)
- https://deel.com/blog/best-contractor-management-software-for-global-payments (12 answers)
- https://papayaglobal.com/blog/10-best-contractor-payment-software (11 answers)

## Warned against

- Venmo: 7 of 7 labels negative. "recommended to avoid using consumer payment apps like Venmo for contractor payments due to compliance risks and high fees" (Llama 4 Maverick, negative prompt)
- Payoneer Workforce Management: 5 of 15 labels negative. "Payoneer has a controversial reputation in the contractor community due to rigid compliance systems and weak customer service" (Gemini 3.5 Flash, negative prompt)
- PayPal MassPay: 6 of 7 labels negative. "avoid ... Consumer Peer-to-Peer & Payment Gateways (e.g., PayPal, Stripe, Venmo) ... these platforms are highly prone to payment disruptions" (Gemini 3.5 Flash, negative prompt)
- Wise Business: 7 of 23 labels negative. "Wise and pure payment tools handle transfers but don't do 1099 filing" (DeepSeek V4 Flash, direct prompt)

## Record

- Method: https://www.gane.ai/index/finance/methodology
- License: CC BY 4.0. Cite as Gane Index, September 2026 Edition, www.gane.ai/index/finance.