Finance AI Index
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Contractor payments · September 2026 Edition

Square Payroll vs Trolley

Zero of twelve models named Square Payroll first on the direct prompt; zero named Trolley. Square Payroll was named by nine of the twelve models and Trolley by ten and both carry 12 labels, so the shares below are directly comparable.

Square Payroll

accepted challenger

Named in one category this edition.

Trolley

accepted challenger

Named in one category this edition.

First-choice share14%7%Of first choices across the direct, paraphrase, budget and scale prompts, 0 to 100.
Negative rate0%0%Negative labels as a share of the product's labels, 0 to 100.
Rank in category#2#5A position in a field of 14; printed, not drawn.
Labels1212Equal, which is what makes the shares comparable.
The two percentage rows are drawn on one 0 to 100 track, Square Payroll reading right to left. Rank and label count are printed, not drawn.Deel was named alongside these two in ten of the twelve direct answers. Deel vs Square Payroll · Deel vs Trolley · Square Payroll vs Tipalti

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; every quote names the model and the prompt it came from. Both figures come from the contractor payments page.

By framing

How many of the twelve models made each the first choice, per way of asking, and how many argued against it.
Square PayrollFirst choices, of twelve modelsTrolley
Direct00
Paraphrase03
Comparative00
Budget-constrained60
Scale-constrained00
Negative00
Bars are first choices, 0 to 12 each sideModels that argued againstA model can name both, so the two sides of a row do not sum to twelve.

Every model, every framing

The seventy-two answers behind the chart above, one cell each: where Square Payroll and Trolley stood in it.
ModelDirectParaphraseComparativeBudget-constrainedScale-constrainedNegative
Claude Haiku 4.5
GPT-5.4 mini
Gemini 3.5 Flash
Perplexity Sonar
Grok 4.1 Fast
Mistral Small
DeepSeek V4 Flash
Llama 4 Maverick
Qwen 3.7 Flash
Kimi K2
GLM 4.7 FlashX
MiniMax M2.5
Square Payroll Trolley first choice named as an alternative argued againstblank: not namedEach cell is one answer, Square Payroll on the left and Trolley on the right.

The direct prompt

The plain question, one answer per model, grouped by where Square Payroll and Trolley stood in it.

Neither was named

12 of 12 modelsThe answer made no first choice from these two in this category.
Claude Haiku 4.5Worksuite alternatives: Deel, Tipalti
GPT-5.4 miniDeel alternatives: Gusto, Tipalti
Gemini 3.5 FlashRippling alternatives: Deel, Remote, Tipalti, Wingspan
Perplexity SonarDeel alternatives: Remote, Tipalti
Grok 4.1 FastRippling alternatives: BILL, Deel, Gusto, Routable
Mistral SmallRoutable alternatives: Deel, Tipalti, Wingspan
DeepSeek V4 FlashTipalti alternatives: BILL, Deel, Routable, Wingspan, Worksuite
Llama 4 MaverickRoutable alternatives: BILL, Wingspan
Qwen 3.7 FlashTipalti alternatives: Deel, Routable
Kimi K2BILL, Gusto alternatives: Routable, Tipalti, Wingspan
GLM 4.7 FlashXDeel, Remote alternatives: Gusto, Oyster / Rippling Global, Routable
MiniMax M2.5Deel alternatives: Gusto, Tipalti

Bold names in an answer are the products the judge labeled a first choice; a model naming several gives each of them that label. The full answer text for every row is in the record.

By buyer segment

The same question asked on behalf of a different buyer. Each standing is computed within its segment and they are never added together. The figures above are the mid-market standing, which is the one the category orders by.
Small business
Square Payroll leads by nine points.
Square Payroll11%#2 of 11
Trolley2%#– of 11
The full small business standing →
Mid-marketThe figures above
Square Payroll leads by seven points.
Square Payroll14%#2 of 14
Trolley7%#5 of 14
The full mid-market standing →
Enterprise
The order flips: Trolley leads at enterprise.
Trolley2%#– of 11
Square Payroll0%#– of 11
The full enterprise standing →

What the models said about Square Payroll

Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Three of four in this category shown.

“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

Every negative label with a quote, up to three, then the highest-weighted positives, up to three. Three of four in this category shown.

“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
Also compared
Deel vs Square PayrollDeel vs TrolleySquare Payroll vs TipaltiSquare Payroll vs RipplingSquare Payroll vs RemoteSquare Payroll vs GustoSquare Payroll vs RoutableTipalti vs TrolleyRippling vs TrolleyTrolley vs RemoteTrolley vs GustoTrolley vs RoutableAll twenty-eight head-to-head pages and the full contractor payments standing

Comparisons are drawn for the top eight products in each category, each against each. The output is the models' output; nothing here is a recommendation by the index.