Finance AI Index
September 2026 Edition · The permanent record of this edition. The unqualified address always carries the latest edition.
Index › Spend and procurement › Contractor payments › Small business › September 2026 Edition

Contractor payments for small business buyers

Asked as “contractor payments and 1099 platform”, and as “freelancer payout software”, on behalf of a small B2B company. 46 first choices recorded across the direct, paraphrase, budget and scale prompts, twelve models each.
Standing
Gusto
Clear leader
59% of first choices, clear leader.
ShowinginAll 41 categories in the September 2026 Edition →

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 leaderThis pageMid-marketDeel27%ContestedStanding →EnterpriseTipalti24%ContestedStanding →

01The standing

Share is the count of first choices across the direct, paraphrase, budget and scale prompts, over all twelve models, for a small B2B company. Ordered by share.
ProductFirst-choice shareNegative rateLabelsQuadrant
01Gusto59%2%55endorsed leader
02Square Payroll11%19%16accepted challenger
03Wingspan4%0%12accepted challenger
04BILL4%17%12accepted challenger
05Wise Business2%9%23accepted challenger
Show the six products at 0%, ordered by negative rate
11PayPal0%90%10criticized challenger
10Tipalti0%23%13accepted challenger
08Rippling0%18%17accepted challenger
09Melio0%15%13accepted challenger
06Deel0%9%45accepted challenger
07Remote0%5%21accepted 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

One product takes 59% of first choices here, so the chart would put ten markers in one corner and one at the far edge. The two measurements it plots are columns in the standing above: share, and the negative label rate. One product carries a negative rate above 25% in this category. Jump to the standing

02What they warned about

Three of twelve models held their first choice under the paraphrase. Claude Haiku 4.5, Gemini 3.5 Flash, Perplexity Sonar, Mistral Small, Llama 4 Maverick, Qwen 3.7 Flash, Kimi K2, GLM 4.7 FlashX and MiniMax M2.5 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.
PayPal
90%
9 of 10 labels negative · 7 of 12 models · 7 hard negative
“Small businesses should be cautious about PayPal, traditional bank wires, and any platform that does not explicitly address compliance” Mistral Small, negative prompt
Venmo
100%
7 of 7 labels negative · 7 of 12 models · 6 hard negative
“Consumer payment apps like PayPal and Venmo may seem convenient for small jobs, but they are often not ideal for growing businesses.” Claude Haiku 4.5, negative prompt
Cash App
100%
5 of 5 labels negative · 5 of 12 models · 4 hard negative
“Peer-to-Peer (P2P) Consumer Apps (e.g., Venmo, Cash App, Zelle, Personal PayPal) ... Why to avoid them” Gemini 3.5 Flash, negative prompt
Stripe
80%
4 of 5 labels negative · 4 of 12 models · 3 hard negative
“Frequent reports of holding funds in "reserves" for 6+ months, account freezes, and delays in payouts” Grok 4.1 Fast, negative 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. 880 links across 230 sites, every framing counted. Ranked by the number of answers carrying the site or page.

worksuite.com
vendor site · Worksuite40 answers · 43 citations · 10 models
learn.g2.com
34 answers · 35 citations · 10 models
remote.com
vendor site · Remote31 answers · 32 citations · 10 models
contractor-of-record.com
30 answers · 30 citations · 9 models
wingspan.app
vendor site · Wingspan29 answers · 33 citations · 10 models
gusto.com
vendor site · Gusto28 answers · 46 citations · 9 models
relayfi.com
18 answers · 18 citations · 7 models
wise.com
16 answers · 23 citations · 6 models
guideflow.com
vendor site · Guideflow16 answers · 16 citations · 9 models
g2.com
15 answers · 21 citations · 8 models
deel.com
vendor site · Deel15 answers · 20 citations · 9 models
riseworks.io
vendor site · Rise Works15 answers · 15 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.

worksuite.com/resources/insights/best-contractor-payment-software
40 answers · 10 models
learn.g2.com/best-contractor-payment-software
34 answers · 10 models
remote.com/blog/payroll/best-contractor-payment-tools
30 answers · 10 models
contractor-of-record.com/software/contractor-payouts
29 answers · 9 models
wingspan.app/articles/best-contractor-payroll-services
23 answers · 9 models
relayfi.com/blog/best-1099-software-small-businesses-guide
18 answers · 7 models
guideflow.com/blog/contractor-payment-software
16 answers · 9 models
riseworks.io/blog/best-payroll-providers-for-automated-contractor-payments-…
15 answers · 9 models
gusto.com/resources/guides/best-contractor-payroll-software
14 answers · 7 models
bolto.com/blog/best-1099-software-for-small-business
12 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 small B2B company?”Paraphrase“Which freelancer payout software would you recommend to a small business that sells to other businesses?”Comparative“What are the top contractor payment platforms for a small team and how do they differ?”Budget-constrained“What is the best contractor payments and 1099 platform for a small company with a tight budget?”Scale-constrained“We are a 30 person company evaluating a contractor payments and 1099 platform. What should we look at?”Negative“Which contractor payment platforms should a small business avoid or be cautious about?”
Claude Haiku 4.5Gusto
Two alternativesQuickBooks, SurePayroll
no first choiceChangedGusto
Three alternativesDeel, Remote, Square Payroll
against: Wise BusinessTax1099
Four alternativesFound, IRS IRIS Portal, QuickBooks Payroll, SurePayroll
no first choiceagainst: PayPal, Venmo
GPT-5.4 miniGusto
Five alternativesBILL, Deel, QuickBooks Contractor Payments, QuickBooks Payroll, Tipalti
GustoHeld
Two alternativesDeel, Tipalti
Gusto
Six alternativesADP RUN, Deel, Justworks, Payoneer Workforce Management, Remote, Rippling
Gusto, Square Payroll
One alternativeFound
no first choicenothing named
Gemini 3.5 FlashGusto
Four alternativesDeel, Melio, Square Payroll, Wingspan
WingspanChanged
Three alternativesDeel, Gusto, Worksuite
against: Wise BusinessGusto, Remote
Two alternativesDeel, Wise Business
against: RipplingFound, QuickBooks Contractor Payments
Three alternativesGusto, Melio, Square Payroll
Gusto
Five alternativesDeel, Remote, Rippling, Wingspan, Worksuite
against: Cash App, Fiverr Enterprise, PayPal, Payoneer, Stripe, Upwork, Venmo, Zelle
Perplexity SonarGusto
Four alternativesADP RUN, Deel, QuickBooks Contractor Payments, QuickBooks Payroll
TrolleyChanged
Three alternativesBILL, Melio, TalentDesk
Gusto
Five alternativesDeel, Melio, Remote, Square Payroll, Wise Business
Gusto, QuickBooks Contractor Payments / Payrollagainst: SurePayrollno first choiceagainst: Venmo
Grok 4.1 FastGusto
Four alternativesBILL, Deel, QuickBooks Online, Rippling
against: BoomTax, Tax1099GustoHeld
One alternativeDeel
Gusto, Wise Business
Three alternativesDeel, Remote, Rippling
Square Payroll
Two alternativesGusto, QuickBooks Contractor Payments
against: Wave PayrollGusto
Three alternativesQuickBooks Payroll, Routable, Trolley
against: BILL, PayPal, Stripe
Mistral SmallGusto, Wingspan
Three alternativesDeel, QuickBooks Contractor Payments, Tipalti
GustoChanged
One alternativeTrolley
Gusto, Square Payroll
Three alternativesDeel, Oyster, Remote
against: Papaya GlobalGusto
Two alternativesADP RUN, Wingspan
no first choiceagainst: PayPal, Traditional Bank Wires
DeepSeek V4 FlashGusto
Two alternativesDeel, QuickBooks Contractor Payments
against: ADP, Paychex, Routable, Tipalti, TrolleyGustoHeld
Two alternativesPayoneer, Wise Business
against: Deel, Papaya Global, PayPal, TipaltiGusto
Five alternativesDeel, Oyster, Remote, Rippling, Wise Business
Square Payroll
Three alternativesGusto, QuickBooks Contractor Payments, Wingspan
ADP RUN, Gusto
One alternativeRippling
against: Deel, Remoteagainst: Airwallex, BILL, Cash App, Jobber, Melio, PayPal, Plowz & Mowz, Square Payroll, Stripe, Venmo, Zelle
Llama 4 Maverickno first choiceGustoChanged
Two alternativesTrevorium, Trolley
Wise Business
Four alternativesDeel, Gusto, Oyster, Remote
no first choiceno first choiceagainst: Cash App, Papaya Global, Square Payroll, Venmo
Qwen 3.7 FlashGusto
Three alternativesDeel, Rippling, Wingspan
BILL, GustoChanged
Two alternativesDeel, Remote
Deel, Gusto
Two alternativesRippling, Wise Business
Square Payroll, Tax1099
Four alternativesGusto, QuickBooks Payments, Track1099, Wise Business
no first choice
Four alternativesDeel, Gusto, Rippling, Thryv
against: Cash App, PayPal, Square Payroll, Stripe, Venmo, Zelle
Kimi K2Gusto
Three alternativesBILL, Deel, Melio
Gusto, Wise BusinessChanged
Two alternativesDeel, Melio
Gusto, Melio
Five alternativesBILL, Deel, Remote, Wingspan, Wise Business
Square Payroll
Two alternativesGusto, QuickBooks Contractor Payments
against: Wave PayrollGusto
Three alternativesDeel, OnPay, Worksuite
against: Deel, Fiverr Enterprise, Freelancer.com, Gusto, PayPal, Payoneer, Upwork, Wave Payroll
GLM 4.7 FlashXRoutable
Three alternativesDeel, Gusto, Tipalti
GustoChanged
Four alternativesDeel, Rippling, Trolley, Wise Business
Deel, Remote
Three alternativesGusto, Rippling, Wise Business
against: Papaya Global, TipaltiGusto
Two alternativesQuickBooks Online, Wave Payroll
no first choiceagainst: Houzz Pro, Melio, Native Teams, Plentific, Rippling
MiniMax M2.5Gusto
Four alternativesDeel, Remote, Wingspan, Worksuite
BILL, GustoChanged
Two alternativesTrolley, Wise Business
Remote
Four alternativesDeel, Gusto, Payoneer, Wise Business
Wave Payroll
Two alternativesGusto, Square Payroll
no first choiceagainst: Cash App, Deel, Payoneer, Rippling, Venmo
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 18:55yes910 s
Direct recommendationGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 19:22yes16 s
Direct recommendationGemini 3.5 Flashgemini-3.5-flash2026-09-17 18:48yes2129 s
Direct recommendationPerplexity Sonarsonar2026-09-17 18:42yes206 s
Direct recommendationGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 20:32yes3717 s
Direct recommendationMistral Smallmistral/mistral-small via mistral2026-09-17 21:04yes517 s
Direct recommendationDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 19:30yes1918 s
Direct recommendationLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 20:47yes53 s
Direct recommendationQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 20:21yes1020 s
Direct recommendationKimi K2moonshotai/kimi-k2 via novita2026-09-17 18:17yes1329 s
Direct recommendationGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 20:53yes1970 s
Direct recommendationMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 19:48yes822 s
ParaphraseClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 19:19no04 s
ParaphraseGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 20:57yes36 s
ParaphraseGemini 3.5 Flashgemini-3.5-flash2026-09-17 18:20yes2025 s
ParaphrasePerplexity Sonarsonar2026-09-17 20:02yes205 s
ParaphraseGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 19:25yes3114 s
ParaphraseMistral Smallmistral/mistral-small via mistral2026-09-17 20:22yes522 s
ParaphraseDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 18:04yes2529 s
ParaphraseLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 20:15yes53 s
ParaphraseQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 21:06yes1440 s
ParaphraseKimi K2moonshotai/kimi-k2 via novita2026-09-17 18:51yes1723 s
ParaphraseGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 18:43yes2330 s
ParaphraseMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 20:01yes1336 s
ComparativeClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 20:12yes99 s
ComparativeGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 19:45yes410 s
ComparativeGemini 3.5 Flashgemini-3.5-flash2026-09-17 18:57yes1825 s
ComparativePerplexity Sonarsonar2026-09-17 19:51yes208 s
ComparativeGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 20:50yes2016 s
ComparativeMistral Smallmistral/mistral-small via mistral2026-09-17 19:44yes56 s
ComparativeDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 18:01yes1924 s
ComparativeLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 20:59yes53 s
ComparativeQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 19:12yes1928 s
ComparativeKimi K2moonshotai/kimi-k2 via novita2026-09-17 19:40yes1344 s
ComparativeGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 18:37yes1389 s
ComparativeMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 19:04yes515 s
Budget constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 19:04yes97 s
Budget constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 19:58yes36 s
Budget constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-17 18:33yes1725 s
Budget constrainedPerplexity Sonarsonar2026-09-17 19:16yes206 s
Budget constrainedGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 21:03yes3819 s
Budget constrainedMistral Smallmistral/mistral-small via mistral2026-09-17 21:08yes53 s
Budget constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 19:33yes1827 s
Budget constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 20:01yes53 s
Budget constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 20:30yes1022 s
Budget constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-17 18:04yes2038 s
Budget constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 18:33yes2498 s
Budget constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 17:58yes1020 s
Scale constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 18:13no06 s
Scale constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 17:57yes57 s
Scale constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-17 21:21yes1251 s
Scale constrainedPerplexity Sonarsonar2026-09-17 20:49yes209 s
Scale constrainedGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 19:24yes1411 s
Scale constrainedMistral Smallmistral/mistral-small via mistral2026-09-17 20:31no07 s
Scale constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 20:01yes915 s
Scale constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 17:57yes53 s
Scale constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 19:02no029 s
Scale constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-17 20:07yes1427 s
Scale constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 18:15yes1244 s
Scale constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 20:17no010 s
Negative framingClaude Haiku 4.5claude-haiku-4-5-202510012026-09-17 19:54yes2713 s
Negative framingGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-17 18:35yes46 s
Negative framingGemini 3.5 Flashgemini-3.5-flash2026-09-17 21:54yes1150 s
Negative framingPerplexity Sonarsonar2026-09-17 18:51yes209 s
Negative framingGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-09-17 18:56yes3716 s
Negative framingMistral Smallmistral/mistral-small via mistral2026-09-17 18:33yes56 s
Negative framingDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-17 17:54yes2028 s
Negative framingLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-17 18:41yes55 s
Negative framingQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-17 20:29yes1542 s
Negative framingKimi K2moonshotai/kimi-k2 via novita2026-09-17 18:05yes2545 s
Negative framingGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-17 20:01yes22112 s
Negative framingMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-17 19:07yes2541 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
BILL.com read as BILL
Bill.com read as BILL
Bill.com (BILL) read as BILL
Patriot read as Patriot Software
QuickBooks Online Payments read as QuickBooks Payments
Square read as Square Payroll
Wave read as Wave Payroll
Unresolved, counted raw
ADP-backed payroll engine + 1099 workflows (custom)
Freelancer.com
Houzz Pro
Justworks
PayFit
Payoneer Workforce Management (Skuad)
Plowz & Mowz
Plutio
QuickBooks Contractor Payments / Payroll
Shortlist
TFY
Thryv
Toptal
Trevorium
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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