Finance AI Index
Index › Spend and procurement › 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
Deel
Contested
27% of first choices, contested.
ShowinginAll 41 categories →

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.
Small businessGusto59%Clear leaderStanding →Mid-marketDeel27%ContestedThis pageEnterpriseTipalti24%ContestedStanding →

01The 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
14Payoneer0%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 vendor page.
Head to head
Deel vs Square PayrollDeel vs TipaltiSquare Payroll vs Tipalti

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%
14Payoneer0%

02What 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 4.1 Fast, 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
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
100%
6 of 6 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

03What they cite

Citations exist only for the models that return a source list: twelve of the twelve in this edition, and all six flagship models on the expanded tier.

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. 6 of those lists are Google grounding redirects that name no site and are left out of the counts. 909 links across 245 sites, every framing counted. Ranked by the number of answers carrying the site or page.

worksuite.com
vendor site · Worksuite37 answers · 39 citations · 10 models
remote.com
vendor site · Remote37 answers · 38 citations · 10 models
contractor-of-record.com
33 answers · 33 citations · 9 models
wingspan.app
vendor site · Wingspan29 answers · 32 citations · 10 models
learn.g2.com
26 answers · 28 citations · 10 models
deel.com
vendor site · Deel21 answers · 34 citations · 9 models
guideflow.com
vendor site · Guideflow21 answers · 21 citations · 9 models
papayaglobal.com
vendor site · Papaya Global17 answers · 21 citations · 7 models
gusto.com
vendor site · Gusto16 answers · 20 citations · 8 models
g2.com
15 answers · 25 citations · 8 models
routable.com
vendor site · Routable15 answers · 24 citations · 9 models
wise.com
15 answers · 15 citations · 6 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.

remote.com/blog/payroll/best-contractor-payment-tools
35 answers · 10 models
worksuite.com/resources/insights/best-contractor-payment-software
35 answers · 10 models
contractor-of-record.com/software/contractor-payouts
33 answers · 9 models
wingspan.app/articles/best-contractor-payroll-services
29 answers · 10 models
learn.g2.com/best-contractor-payment-software
26 answers · 10 models
guideflow.com/blog/contractor-payment-software
18 answers · 9 models
routable.com/resources/best-1099-automation-platforms-high-volume-businesses
13 answers · 8 models
riseworks.io/blog/best-payroll-providers-for-automated-contractor-payments-…
12 answers · 7 models
costbench.com/best/best-contractor-payment-platforms
10 answers · 6 models
deel.com/blog/best-contractor-management-software-for-global-payments
10 answers · 7 models

04How 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.
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, Payoneer, Wise Business
GPT-5.4 miniDeel
Two alternativesGusto, Tipalti
DeelHeld
Four alternativesGusto, Rippling, Tipalti, Trolley
Deel
Four alternativesGusto, Payoneer, Remote, Wise Business
against: RipplingSquare Payroll
One alternativeGusto
against: BILL, Deel, Tipaltino first choiceagainst: G-P, Wave Payroll, WorkMarket, Worksome
Gemini 3.5 FlashRippling
Four alternativesDeel, Remote, Tipalti, Wingspan
against: Gusto, QuickBooksDeel, TipaltiChanged
Two alternativesWingspan, Worksuite
against: Wise BusinessDeel
Seven alternativesGusto, Oyster, Remote, Rippling, Tipalti, Wingspan, Worksuite
against: Wise BusinessMelio
Four alternativesGusto, Square Payroll, Tax1099, WageFiling
no first choice
Ten alternativesBILL, Deel, Lano, Oyster, Remote, Rippling, Routable, Tipalti, Wingspan, Worksuite
against: PayPal, Venmoagainst: BILL, PayPal, Payoneer, Rippling, Stripe, 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 BusinessSurePayroll
Two alternativesBILL, QuickBooks Payroll / Contractor Payments
no first choiceagainst: Venmo
Grok 4.1 FastRippling
Four alternativesBILL, Deel, Gusto, Routable
DeelChanged
Six alternativesGusto, Payoneer, Remote, Rippling, Trolley, Wise Business
against: Papaya GlobalDeel, Remote
Eight alternativesGusto, Multiplier, Papaya Global, Payoneer, Rippling, Tipalti, Wise Business, Worksuite
Square Payroll
Three alternativesGusto, Patriot Software, QuickBooks Contractor Payments
against: Avalara, Track1099Gusto, 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 BusinessRelay, Rise Works
Two alternativesQuickBooks Contractor Payments, Wingspan
no first choiceagainst: PayPal, Traditional Bank Wires
DeepSeek V4 FlashTipalti
Five alternativesBILL, Deel, Routable, Wingspan, Worksuite
against: Gusto, QuickBooks, Wise BusinessDeelChanged
Five alternativesGusto, Papaya Global, Remote, Trolley, Wise Business
Deel
Six alternativesPapaya Global, Payoneer, 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
Llama 4 MaverickRoutable
Two alternativesBILL, Wingspan
TrolleyChangedPapaya Global
Nine alternatives4dev.com, Deel, Gusto, Hyperwallet, Payoneer, Stripe, Tipalti, Wise Business, Worksuite
no first choice
One alternativeWingspan
no first choiceagainst: Venmo
Qwen 3.7 FlashTipalti
Two alternativesDeel, Routable
against: Gusto, QuickBooks Contractor PaymentsDeelChanged
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, MoneyGram, PayPal, 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, Paychexno first choiceagainst: Cash App, Fiverr Enterprise, PayPal, Payoneer, Upwork, Venmo, Zelle
GLM 4.7 FlashXDeel, Remote
Three alternativesGusto, Oyster / Rippling Global, Routable
Papaya GlobalChanged
Three alternativesDeel, Gusto, Trolley
Deel, Remote, Worksuite
Eleven alternativesFiverr Enterprise, Gusto, Multiplier, Papaya Global, Payoneer, Procore Pay, Rippling, Stripe, Tipalti, Veem, Wise Business
Square Payroll
Two alternativesTrack1099, Wave Payroll
against: Gustono 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
Bold is the first choiceAlternatives are counted; the count opens them.What the answer argued against

05The record

One row per call: the version string exactly as returned, whether the model searched, sources cited, and latency. Full answer text is in the free responses file. Download the record
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 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 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 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 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 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 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 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 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 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 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 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 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.

Category-scoped readings
Avalara 1099 read as Avalara
Bill.com read as BILL
Patriot read as Patriot Software
Rise read as Rise Works
Square read as Square Payroll
Wave read as Wave Payroll
Unresolved, counted raw
1099Online
Appen (formerly CrowdGen)
BuildSafe
Checkr
Coinbase
Gusto Ramp
HomePay
Keka
Lano
Optionz
Oyster / Rippling Global
Pluckwalk Technologies
QuickBooks Payroll / Contractor Payments
Rapid Express Check Cashing
RemotePass
Uniswap
Workana
Workful
Workstream
Discontinued, still offered
No shut-down product was recommended here.

Also in spend and procurement

The other categories of this function, with the leader in each.
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