September 2026 Edition, published · The permanent record of that edition, superseded since. The current standing is on the category page →
Index › Finance › Spend and procurement › Contractor payments · September 2026 Edition

Contractor payments

Asked as “contractor payments and 1099 platform”, and as “freelancer payout software”, on behalf of a mid-market B2B company. 44 first choices recorded across the direct, paraphrase, budget and scale prompts, twelve models each.
Standing · first-choice share
27%
Contested · Square Payroll 14%
27Deel14Square Payroll07Rippling52others

27% of first choices, contested.

By buyer segment

The same question asked on behalf of a different buyer. Each standing is computed within its segment; they sit side by side and are never added together.

The standing

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. Ordered by share.
ProductFirst-choice shareNegative rateLabelsQuadrant
01Deel27%4%49accepted challenger
02Square Payroll14%0%12accepted challenger
03Tipalti7%4%24accepted challenger
04Rippling7%11%27accepted challenger
05Trolley7%0%12accepted challenger
06Remote5%0%28accepted challenger
07Gusto5%11%37accepted challenger
08Routable5%0%11accepted challenger
09Papaya Global2%5%19accepted challenger
10Worksuite2%0%17accepted challenger
11BILL2%20%15accepted challenger
Show the three products at 0%, ordered by negative rate
14Payoneer Workforce Management0%33%15criticized challenger
13Wise Business0%30%23criticized challenger
12Wingspan0%0%17accepted challenger
Bars are the share of first choices, 0 to 100Every product with at least 10 labels here. Every product name links to its product page.
All twenty-eight head-to-head pages: the top eight products, each against each

Recommended versus criticized

Every product with at least 10 labels here, on both axes. The 30% line names a quadrant, not the verdict above: that one needs more than 40%.

Criticized challengerCriticized default
Negative label rate →
01
02
03
04
05
06
07
08
09
10
11
12
13
14
Accepted challengerEndorsed leader
0%First-choice share → · lines at 30% share and 25% negative40%
Key
01Deel27%
02Square Payroll14%
03Tipalti7%
04Rippling7%
05Trolley7%
06Remote5%
07Gusto5%
08Routable5%
09Papaya Global2%
10Worksuite2%
11BILL2%
12Wingspan0%
13Wise Business0%
14Payoneer Workforce Management0%

What they warned about

Two of twelve models held their first choice under the paraphrase. Claude Haiku 4.5, Gemini 3.5 Flash, Perplexity Sonar, Grok 4.20, Mistral Small, DeepSeek V4 Flash, Llama 4 Maverick, Qwen 3.7 Flash, Kimi K2 and GLM 4.7 FlashX changed. A high negative share on a product with few labels is a warning. A low share on a product with many labels is salience, not sentiment.
Venmo
100%
7 of 7 labels negative · 6 of 12 models · 7 hard 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
33%
5 of 15 labels negative · 5 of 12 models · 4 hard 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
86%
6 of 7 labels negative · 5 of 12 models · 3 hard 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
30%
7 of 23 labels negative · 5 of 12 models · 1 hard negative
“Wise and pure payment tools handle transfers but don't do 1099 filing” DeepSeek V4 Flash, direct prompt

What they cite

Twelve of the twelve models returned a source list in this edition: four return the pages they cited and eight the search results they consulted.

Sites the answers cite

67 of 72 answers in this category came back with a source list, from 12 of 12 models: citations where the model returns them, or the search results it consulted. 1012 links across 262 sites, every framing counted. Ranked by the number of answers carrying the site or page.

vendor site · Worksuite42 answers · 47 citations · 11 models
vendor site · Remote39 answers · 40 citations · 11 models
vendor site · Wingspan33 answers · 40 citations · 11 models
33 answers · 33 citations · 9 models
vendor site · G228 answers · 31 citations · 11 models
vendor site · Deel23 answers · 37 citations · 10 models
vendor site · Guideflow23 answers · 24 citations · 10 models
vendor site · Papaya Global20 answers · 24 citations · 8 models
vendor site · G218 answers · 28 citations · 9 models
vendor site · Gusto18 answers · 23 citations · 9 models
17 answers · 17 citations · 7 models
vendor site · Routable15 answers · 24 citations · 9 models

Pages the answers cite

The ten pages named in the most answers, by full address. A page here is one the models returned with a recommendation, not one the index endorses.

Search against answers

Each company's standing in the answers beside its site's footprint in Google search, one row a site: the products the models named on it with their shares, and the share they add up to; monthly searches on Google, and DataForSEO's estimate of AI search demand (modeled from search signals, directional, not a count of queries to any assistant), for the most-searched of the company's and its products' names (the name is in each row's hover text); estimated monthly organic visits to the site; and its best position in Google's top ten for “best contractor payments and 1099 platform”, “contractor payment platforms”, “contractor payments and 1099 platform”. US estimates from DataForSEO and Google's Ads Transparency Center. A small company's site, or a mid-sized company's site for its flagship, is marked company; a product on a large parent's site (Google, Microsoft) has no site figures. A column with no figures for this category is left out, and an empty cell means none were seen, not none exist. Two measurements side by side: neither is read as the cause of the other.
Company and productsShareOwn site citedName searches, GoogleAI search demand, est.Organic visitsPaid search a month, est.Google ads, last 30 daysBest Google position
Deel deel.com27%17240,5001,210307,175$330,608118
Square squareup.com
Square Payroll 14%
14%531,000,000497,5263,658,565 company$9993
Tipalti tipalti.com7%49018,100381213,652$83,3631203
Rippling rippling.com7%90301,00017,886712,399$42,013115
Trolley trolley.com7%1849,50027,83220,61030
Remote remote.com5%85110,000426,655766,598$15,85888
Gusto gusto.com5%129673,00010,5601,629,483118
Routable routable.com5%221,3001145,890$1,10872
QuickBooks parent site
QuickBooks Contractor Payments 5%
5%501,000,00054,681
Papaya Global papayaglobal.com2%491,60050189,744$8,30911

Google's top ten for the three searches hold 22 sites; 3 of them are among the sites the models cited here (routable.com, wise.com, worksuite.com). The first result for “best contractor payments and 1099 platform” is wise.com.

How they answered

Six framings of the same buying question, each sent to every model in a fresh session with search on. One row per model, so a row shows whether it held its answer under rewording, what it named when cost was the constraint, and what it argued against. Computed from the raw judge labels.
ShowHide
ModelDirect“What is the best contractor payments and 1099 platform for a mid-market B2B company?”Paraphrase“Which freelancer payout software would you recommend to a mid-sized B2B company?”Comparative“What are the top contractor payment platforms and how do they differ?”Budget-constrained“What is the best contractor payments and 1099 platform for a company with a limited budget?”Scale-constrained“We are a 500 person company evaluating a contractor payments and 1099 platform. What should we look at?”Negative“Which contractor payment platforms should I avoid or be cautious about?”
Claude Haiku 4.5Worksuite
Two alternativesDeel, Tipalti
no first choiceChangedDeel
Two alternativesRemote, Worksuite
Patriot Software, Square Payroll
Three alternativesOnPay, QuickBooks Online, WageFiling
no first choiceagainst: Cash App, PayPal MassPay, Payoneer Workforce Management, Wise Business
GPT-5.4 miniDeel
Two alternativesGusto, Tipalti
DeelHeld
Four alternativesGusto, Rippling, Tipalti, Trolley
Deel
Four alternativesGusto, Payoneer Workforce Management, Remote, Wise Business
against: Rippling
Square Payroll
One alternativeGusto
against: BILL, Deel, Tipalti
no first choiceagainst: G-P, Wave Payroll, WorkMarket, Worksome
Gemini 3.5 FlashRippling
Four alternativesDeel, Remote, Tipalti, Wingspan
against: Gusto, QuickBooks Contractor Payments
Deel, TipaltiChanged
Two alternativesWingspan, Worksuite
against: Wise Business
Deel
Seven alternativesGusto, Oyster, Remote, Rippling, Tipalti, Wingspan, Worksuite
against: Wise Business
Melio
Four alternativesGusto, Square Payroll, Tax1099, WageFiling
no first choice
Ten alternativesBILL, Deel, Lano, Oyster, Remote, Rippling, Routable, Tipalti, Wingspan, Worksuite
against: PayPal MassPay, Venmo
against: BILL, PayPal MassPay, Payoneer Workforce Management, Rippling, Stripe Connect, Venmo, Wise Business
Perplexity SonarDeel
Two alternativesRemote, Tipalti
TrolleyChanged
Three alternativesFiverr Enterprise, Hyperwallet, Papaya Global
Deel, Worksuite
Four alternativesGCPay, Gusto, Procore Pay, Tipalti
against: QuickBooks Payments, Wise Business
SurePayroll
Two alternativesBILL, QuickBooks Payroll
no first choiceagainst: Venmo
Grok 4.20Rippling
Four alternativesBILL, Deel, Gusto, Routable
DeelChanged
Six alternativesGusto, Payoneer Workforce Management, Remote, Rippling, Trolley, Wise Business
against: Papaya Global
Deel, Remote
Eight alternativesGusto, Multiplier, Papaya Global, Payoneer Workforce Management, Rippling, Tipalti, Wise Business, Worksuite
Square Payroll
Three alternativesGusto, Patriot Software, QuickBooks Contractor Payments
against: Track1099
Gusto, Rippling
Three alternativesDeel, OnPay, Remote
against: Ontop, RemotePass, WorkMarket
Mistral SmallRoutable
Three alternativesDeel, Tipalti, Wingspan
TrolleyChanged
One alternativeFiverr Enterprise
Worksuite
Six alternativesDeel, Gusto, Papaya Global, Procore Pay, Remote, Tipalti
against: Wise Business
Relay, Rise Works
Two alternativesQuickBooks Contractor Payments, Wingspan
no first choiceagainst: PayPal MassPay, Traditional Bank Wires
DeepSeek V4 FlashTipalti
Five alternativesBILL, Deel, Routable, Wingspan, Worksuite
against: Gusto, QuickBooks Contractor Payments, Wise Business
DeelChanged
Five alternativesGusto, Papaya Global, Remote, Trolley, Wise Business
Deel
Six alternativesPapaya Global, Payoneer Workforce Management, Remote, Rippling, Tipalti, Wise Business
QuickBooks Contractor Payments
Two alternativesGusto, Square Payroll
no first choice
Seven alternativesDeel, Multiplier, Remote, Rippling, Tipalti, WorkMarket, Workday
against: BILL, Deel, Hyperwallet, Ontop, Payoneer Workforce Management
Llama 4 MaverickRoutable
Two alternativesBILL, Wingspan
TrolleyChangedPapaya Global
Nine alternatives4dev.com, Deel, Gusto, Hyperwallet, Payoneer Workforce Management, Stripe Connect, Tipalti, Wise Business, Worksuite
no first choice
One alternativeWingspan
no first choiceagainst: Venmo
Qwen 3.7 FlashTipalti
Two alternativesDeel, Routable
against: Gusto, QuickBooks Contractor Payments
DeelChanged
Three alternativesPapaya Global, Rippling, Trolley
no first choice
Four alternativesBILL, Deel, Gusto, Rippling
Square Payroll
Two alternativesPatriot Software, SurePayroll
no first choice
Nine alternativesBILL, Deel, Gusto Ramp, Keka, Oyster, Remote, Rippling, Square Payroll, Workstream
against: Cash App, Coinbase Business, MoneyGram, PayPal MassPay, Rapid Express Check Cashing, Uniswap, Venmo, Western Union, Zelle
Kimi K2BILL, Gusto
Three alternativesRoutable, Tipalti, Wingspan
DeelChanged
Four alternativesGusto, Papaya Global, Trolley, Wise Business
Deel
Six alternativesGusto, Remote, Rippling, Tipalti, Wise Business, Worksuite
QuickBooks Contractor Payments, Square Payroll
Two alternativesGusto, Papaya Global
against: ADP, Paychex
no first choiceagainst: Cash App, Fiverr Enterprise, PayPal MassPay, Payoneer Workforce Management, Upwork, Venmo, Zelle
GLM 4.7 FlashXDeel, Remote
Three alternativesGusto, Oyster, Routable
Papaya GlobalChanged
Three alternativesDeel, Gusto, Trolley
Deel, Remote, Worksuite
Eleven alternativesFiverr Enterprise, Gusto, Multiplier, Papaya Global, Payoneer Workforce Management, Procore Pay, Rippling, Stripe Connect, Tipalti, Veem, Wise Business
Square Payroll
Two alternativesTrack1099, Wave Payroll
against: Gusto
no first choiceagainst: QuickBooks Payroll, Tax1099against: Appen, Cash App, Pluckwalk Technologies, Rippling, Venmo, Zelle
MiniMax M2.5Deel
Two alternativesGusto, Tipalti
DeelHeld
Three alternativesPapaya Global, Rippling, Trolley
Deel
Seven alternativesGusto, Multiplier, Papaya Global, Remote, Rippling, Tipalti, Wise Business
Found
Two alternativesQuickBooks Contractor Payments, Square Payroll
Deel, Remote
Two alternativesRoutable, Worksome
against: Payoneer Workforce Management
Bold is the first choiceAlternatives are counted; the count opens them.What the answer argued against

The record

One row per call: the version string exactly as returned, whether the model searched, sources cited, and latency.
Seventy-two rows: every prompt, every model, every answer.
PromptModelVersion stringTime (UTC)SearchedSourcesLatency
Direct recommendationClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 18:16yes1610 s
Direct recommendationGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 18:29yes55 s
Direct recommendationGemini 3.5 Flashgemini-3.5-flash2026-09-17 18:49yes1529 s
Direct recommendationPerplexity Sonarsonar2026-09-17 18:38yes206 s
Direct recommendationGrok 4.20spacexai/grok-4.1-fast-non-reasoning via vertex (asked for grok-4.20-non-reasoning; the API answered as this version)2026-09-17 17:56yes3720 s
Direct recommendationMistral Smallmistral/mistral-small via mistral2026-09-17 19:11yes55 s
Direct recommendationDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 19:26yes1725 s
Direct recommendationLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 18:49yes53 s
Direct recommendationQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 20:17yes1339 s
Direct recommendationKimi K2moonshotai/kimi-k2 via novita2026-09-17 18:10yes1422 s
Direct recommendationGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 19:16yes1559 s
Direct recommendationMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 20:13yes547 s
ParaphraseClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 19:26no04 s
ParaphraseGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 19:16yes46 s
ParaphraseGemini 3.5 Flashgemini-3.5-flash2026-09-17 19:56yes1721 s
ParaphrasePerplexity Sonarsonar2026-09-17 19:44yes205 s
ParaphraseGrok 4.20spacexai/grok-4.1-fast-non-reasoning via vertex (asked for grok-4.20-non-reasoning; the API answered as this version)2026-09-17 18:46yes2915 s
ParaphraseMistral Smallmistral/mistral-small via mistral2026-09-17 19:19yes54 s
ParaphraseDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 19:08yes2929 s
ParaphraseLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 17:54yes53 s
ParaphraseQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 21:06yes1551 s
ParaphraseKimi K2moonshotai/kimi-k2 via novita2026-09-17 20:18yes1429 s
ParaphraseGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 19:49yes2867 s
ParaphraseMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 20:10yes1829 s
ComparativeClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 20:04yes98 s
ComparativeGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 18:13yes57 s
ComparativeGemini 3.5 Flashgemini-3.5-flash2026-09-17 18:01yes1420 s
ComparativePerplexity Sonarsonar2026-09-17 19:05yes2012 s
ComparativeGrok 4.20spacexai/grok-4.1-fast-non-reasoning via vertex (asked for grok-4.20-non-reasoning; the API answered as this version)2026-09-17 20:47yes1814 s
ComparativeMistral Smallmistral/mistral-small via mistral2026-09-17 18:39yes59 s
ComparativeDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-09-17 19:32yes1950 s
ComparativeLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 18:17yes53 s
ComparativeQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 20:47no029 s
ComparativeKimi K2moonshotai/kimi-k2 via novita2026-09-17 20:05yes826 s
ComparativeGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 20:39yes13125 s
ComparativeMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 20:38yes1028 s
Budget constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 20:10yes1610 s
Budget constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 20:44yes45 s
Budget constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-17 19:19yes2329 s
Budget constrainedPerplexity Sonarsonar2026-09-17 19:21yes204 s
Budget constrainedGrok 4.20spacexai/grok-4.1-fast-non-reasoning via vertex (asked for grok-4.20-non-reasoning; the API answered as this version)2026-09-17 18:23yes3817 s
Budget constrainedMistral Smallmistral/mistral-small via mistral2026-09-17 19:59yes88 s
Budget constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 20:34yes1916 s
Budget constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 19:30yes53 s
Budget constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 19:00yes2495 s
Budget constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-17 19:17yes919 s
Budget constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 19:41yes2564 s
Budget constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 21:01yes1236 s
Scale constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 21:09no07 s
Scale constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 21:05yes28 s
Scale constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-17 19:29yes1528 s
Scale constrainedPerplexity Sonarsonar2026-09-17 19:26yes1720 s
Scale constrainedGrok 4.20spacexai/grok-4.1-fast-non-reasoning via vertex (asked for grok-4.20-non-reasoning; the API answered as this version)2026-09-17 19:38yes1411 s
Scale constrainedMistral Smallmistral/mistral-small via mistral2026-09-17 21:01no07 s
Scale constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 21:03yes2023 s
Scale constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 21:07yes54 s
Scale constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 18:24no029 s
Scale constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-17 19:38yes1229 s
Scale constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 20:21yes1436 s
Scale constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 18:19yes920 s
Negative framingClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 20:12yes199 s
Negative framingGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 20:59yes26 s
Negative framingGemini 3.5 Flashgemini-3.5-flash2026-09-17 19:46yes1923 s
Negative framingPerplexity Sonarsonar2026-09-17 19:46yes207 s
Negative framingGrok 4.20spacexai/grok-4.1-fast-non-reasoning via vertex (asked for grok-4.20-non-reasoning; the API answered as this version)2026-09-17 20:05yes4216 s
Negative framingMistral Smallmistral/mistral-small via mistral2026-09-17 20:58yes56 s
Negative framingDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 20:27yes3022 s
Negative framingLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 18:29yes53 s
Negative framingQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 19:53yes1028 s
Negative framingKimi K2moonshotai/kimi-k2 via novita2026-09-17 19:47yes3039 s
Negative framingGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 21:00yes2799 s
Negative framingMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 19:58yes1521 s

Normalization in this category

Every judgment call made between the raw labels and the numbers above, listed so it is visible and reversible.

ShowHide
Category-scoped readings
Avalara read as Track1099
Avalara 1099 read as Track1099
Bill.com read as BILL
Patriot read as Patriot Software
PayPal read as PayPal MassPay
PayPal "Friends & Family." read as PayPal MassPay
Payoneer read as Payoneer Workforce Management
QuickBooks read as QuickBooks Contractor Payments
Rise read as Rise Works
Square read as Square Payroll
Stripe read as Stripe Connect
Wave read as Wave Payroll
Unresolved, counted raw
Appen (formerly CrowdGen)
BuildSafe
Checkr
Gusto Ramp
HomePay
Keka
Lano
Optionz
Pluckwalk Technologies
Rapid Express Check Cashing
RemotePass
Uniswap
Workana
Workstream
Discontinued, still offered
No shut-down product was recommended here.
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