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Contractor payments · October 2026 Edition

Square Payroll vs Wingspan

Zero of fourteen models named Square Payroll first on the direct prompt; zero named Wingspan. Square Payroll was named by nine of the fourteen models and Wingspan by nine and Square Payroll carries 11 labels and Wingspan 15, so the shares are not directly comparable.

Square Payroll

accepted challenger

Named in one category this edition.

Wingspan

accepted challenger

Named in one category this edition.

First-choice share8%6%Of first choices across the direct, paraphrase, budget and scale prompts, 0 to 100.

Negative rate9%0%Negative labels as a share of the product's labels, 0 to 100.

Rank in category#5#6A position in a field of 13; printed, not drawn.

Labels1115A count; the two differ.

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.Tipalti was named alongside these two in twelve of the fourteen direct answers. Tipalti vs Square Payroll · Tipalti vs Wingspan · Deel vs Square Payroll

Share is the count of first choices across the direct, paraphrase, budget and scale prompts over all fourteen 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 fourteen models made each the first choice, per way of asking, and how many argued against it.

Square PayrollFirst choices, of fourteen modelsWingspan

Direct00

Paraphrase03

Comparative00

Budget-constrained40

Scale-constrained00

Negative001 against Square Payroll

Bars are first choices, 0 to 14 each sideModels that argued againstA model can name both, so the two sides of a row do not sum to fourteen.

Every model, every framing

The eighty-four answers behind the chart above, one cell each: where Square Payroll and Wingspan stood in it.

Model	Direct	Paraphrase	Comparative	Budget-constrained	Scale-constrained	Negative
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
GPT-6 Luna
Muse Glimmer 30B

Square Payroll

Wingspan

first choice

named as an alternative

argued againstblank: not namedEach cell is one answer, Square Payroll on the left and Wingspan on the right.

The direct prompt

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

Neither was the first choice, one was named

3 of 14 modelsThe answer put something else first and named one of the two as an alternative.

Claude Haiku 4.5Tipalti alternatives: Gusto, Remote, Wingspan, Worksuite

Gemini 3.5 FlashWorksuite alternatives: Deel, Rippling, Tipalti, Wingspan

Muse Glimmer 30BTipalti alternatives: Deel, Gusto, Trolley, Wingspan

Neither was named

11 of 14 modelsThe answer made no first choice from these two in this category.

GPT-5.4 miniTipalti alternatives: BILL, Deel, Rippling

Perplexity SonarDeel alternatives: BILL, Tipalti

Grok 4.1 FastRippling alternatives: Deel, Gusto

Mistral SmallDeel, Tipalti alternatives: BILL

DeepSeek V4 FlashTipalti alternatives: BILL, Rippling

Llama 4 MaverickGusto alternatives: Deel, Tipalti

Qwen 3.7 FlashRippling, Tipalti alternatives: BILL, Deel, Gusto

Kimi K2Tipalti alternatives: BILL, Gusto, Rippling, Routable

GLM 4.7 FlashXDeel alternatives: 1099Online, Gusto, Remote, Rippling, Tipalti

MiniMax M2.5Deel, Papaya Global alternatives: BILL, Remote, Rippling

GPT-6 LunaBILL 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 ten points.

Square Payroll#2 of 13

Wingspan#11 of 13

The full small business standing →

Mid-marketThe figures above

Square Payroll leads by two points.

Square Payroll#5 of 13

Wingspan#6 of 13

The full mid-market standing →

Enterprise

The order flips: Wingspan leads at enterprise.

Wingspan#5 of 13

Square Payroll#– of 13

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. Four of five in this category shown.

“Platforms to use with caution: Stripe, Square, PayPal Business.” Gemini 3.5 Flash · negative prompt · soft negative

“Square Payroll's Contractor-Only plan stands out as the best option for a company on a limited budget” Grok 4.1 Fast · budget prompt · first choice

“Square Payroll is my budget pick if you want payments and 1099-NEC filing in one place” GPT-6 Luna · budget prompt · first choice

“Square Payroll if you only care about paying contractors as cheaply as possible” Perplexity Sonar · budget prompt · first choice

What the models said about Wingspan

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

“or Wingspan if your focus is specifically on contractor management with strong ERP integrations. Both offer the scalability mid-sized companies need” MiniMax M2.5 · paraphrase prompt · first choice

“Wingspan is the most purpose-built fit” Muse Glimmer 30B · paraphrase prompt · first choice

“Top Pick: Wingspan” Kimi K2 · paraphrase prompt · first choice

Also compared

Tipalti vs Square Payroll Tipalti vs Wingspan Deel vs Square Payroll Deel vs Wingspan Rippling vs Square Payroll Rippling vs Wingspan Gusto vs Square Payroll Gusto vs Wingspan Square Payroll vs QuickBooks Contractor Payments Square Payroll vs Remote Wingspan vs QuickBooks Contractor Payments Wingspan vs Remote All 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.