# Square Payroll vs Trolley: which do AI models recommend for contractor payments, September 2026

Finance AI Recommendation Index, September 2026 Edition, Contractor payments. Zero of twelve models named Square Payroll first on the direct prompt; zero named Trolley. Page: https://finance-ai-index.com/spend/contractor-payments/square-payroll-vs-trolley/

| | First-choice share | Rank | Negative rate | Labels | Models naming it |
|---|---|---|---|---|---|
| Square Payroll | 14% | #2 of 14 | 0% | 12 | 9 of 12 |
| Trolley | 7% | #5 of 14 | 0% | 12 | 10 of 12 |

## The direct prompt, model by model

- Claude Haiku 4.5: neither named (first choices: Worksuite) (alternatives: Deel, Tipalti)
- GPT-5.4 mini: neither named (first choices: Deel) (alternatives: Gusto, Tipalti)
- Gemini 3.5 Flash: neither named (first choices: Rippling) (alternatives: Deel, Remote, Tipalti, Wingspan)
- Perplexity Sonar: neither named (first choices: Deel) (alternatives: Remote, Tipalti)
- Grok 4.1 Fast: neither named (first choices: Rippling) (alternatives: BILL, Deel, Gusto, Routable)
- Mistral Small: neither named (first choices: Routable) (alternatives: Deel, Tipalti, Wingspan)
- DeepSeek V4 Flash: neither named (first choices: Tipalti) (alternatives: BILL, Deel, Routable, Wingspan, Worksuite)
- Llama 4 Maverick: neither named (first choices: Routable) (alternatives: BILL, Wingspan)
- Qwen 3.7 Flash: neither named (first choices: Tipalti) (alternatives: Deel, Routable)
- Kimi K2: neither named (first choices: BILL, Gusto) (alternatives: Routable, Tipalti, Wingspan)
- GLM 4.7 FlashX: neither named (first choices: Deel, Remote) (alternatives: Gusto, Oyster / Rippling Global, Routable)
- MiniMax M2.5: neither named (first choices: Deel) (alternatives: Gusto, Tipalti)

## What the models said about Square Payroll

- "I'd recommend starting with Patriot Software or Square Payroll since they have the lowest ongoing costs" (Claude Haiku 4.5, budget prompt, first choice)
- "Square Payroll's contractor-only plan stands out as the best option for a company with a limited budget." (Grok 4.1 Fast, budget prompt, first choice)
- "Based on your requirement for a limited budget, the best platform is Square Payroll." (GLM 4.7 FlashX, budget prompt, first choice)

## What the models said about Trolley

- "Trolley is a recommended freelancer payout software for mid-sized B2B companies" (Llama 4 Maverick, paraphrase prompt, first choice)
- "I'd recommend Trolley as the best overall starting point" (Perplexity Sonar, paraphrase prompt, first choice)
- "Trolley is highly recommended for freelancer payouts" (Mistral Small, paraphrase prompt, first choice)

Share is the count of first choices across the direct, paraphrase, budget and scale prompts over all twelve models, for a mid-market B2B company; rank is within the category. Comparisons are drawn for the top eight products in each category. Published under CC BY 4.0; the output is the models' output, and nothing here is a recommendation by the index.