AI Indexes
Finance AI Index
September 2026 Edition, published September 17, 2026 · The permanent record of that edition, superseded since. The current standing is on the category page →
Index › Tax and compliance › Sales tax automation › Small business › September 2026 Edition

Sales tax automation for small business buyers

Asked as “sales tax compliance software”, and as “sales tax calculation and filing tool”, on behalf of a small B2B company. 55 first choices recorded across the direct, paraphrase, budget and scale prompts, twelve models each.
Standing · first-choice share
33%
Contested · TaxCloud 31%
33TaxJar31TaxCloud15Avalara AvaTax22others

33% 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 small B2B company. Ordered by share.
ProductFirst-choice shareNegative rateLabelsQuadrant
01TaxJar33%12%68endorsed leader
02TaxCloud31%5%59endorsed leader
03Avalara AvaTax15%58%57criticized challenger
04Anrok7%7%15accepted challenger
05Zoho Books5%0%13accepted challenger
06Zamp4%0%12accepted challenger
07Stripe Tax2%4%26accepted challenger
08Kintsugi2%18%11accepted challenger
Show the three products at 0%, ordered by negative rate
11Vertex0%69%32criticized challenger
10Numeral0%21%14accepted challenger
09Quaderno0%0%10accepted 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 ten head-to-head pages: the top five 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
Accepted challengerEndorsed leader
0%First-choice share → · lines at 30% share and 25% negative50%
Key
01TaxJar33%
02TaxCloud31%
03Avalara AvaTax15%
04Anrok7%
05Zoho Books5%
06Zamp4%
07Stripe Tax2%
08Kintsugi2%
09Quaderno0%
10Numeral0%
11Vertex0%

What they warned about

Four of twelve models held their first choice under the paraphrase. Claude Haiku 4.5, Perplexity Sonar, Mistral Small, DeepSeek V4 Flash, Llama 4 Maverick, 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.
Avalara AvaTax
58%
33 of 57 labels negative · 13 of 12 models · 5 hard negative
“Typically Not Recommended for Small Businesses: **Avalara & Vertex O Series:** Industry leaders but designed for mid-market to enterprise” Qwen 3.7 Flash, direct prompt
Vertex
69%
22 of 32 labels negative · 12 of 12 models · 7 hard negative
“Vertex is prohibitively expensive for most small to mid-sized businesses, and implementation complexity can result in lengthy rollout timelines” Claude Haiku 4.5, negative prompt
TaxJar
12%
8 of 68 labels negative · 7 of 12 models · 3 hard negative
“Avoid TaxJar if a large part of your revenue is tax-exempt resale; it is optimized for taxable e-commerce.” Muse Glimmer 30B, direct prompt
Sovos
62%
5 of 8 labels negative · 4 of 12 models · 3 hard negative
“Enterprise-Grade Giants (Vertex, Sovos, Thomson Reuters ONESOURCE) ... Why small businesses should avoid them” Gemini 3.5 Flash, negative prompt

What they cite

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

Sites the answers cite

79 of 84 answers in this category came back with a source list, from 14 of 12 models: citations where the model returns them, or the search results it consulted. 1036 links across 114 sites, every framing counted. Ranked by the number of answers carrying the site or page.

vendor site · TaxCloud65 answers · 137 citations · 14 models
vendor site · TaxJar50 answers · 68 citations · 14 models
vendor site · Commenda42 answers · 53 citations · 12 models
vendor site · Zamp37 answers · 59 citations · 12 models
vendor site · Avalara36 answers · 71 citations · 13 models
vendor site · G234 answers · 37 citations · 11 models
vendor site · Taxwire31 answers · 36 citations · 12 models
vendor site · G227 answers · 50 citations · 8 models
vendor site · Guideflow26 answers · 32 citations · 10 models
vendor site · Wolters Kluwer26 answers · 26 citations · 9 models
25 answers · 26 citations · 10 models
vendor site · Thomson Reuters20 answers · 29 citations · 10 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 sales tax compliance software”, “sales tax compliance software”, “sales tax tools”. 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
TaxJar taxjar.com33%1746,60063181,783$119552
TaxCloud taxcloud.com31%1031,00024229,957448
Avalara avalara.com
Avalara AvaTax 15%, Avalara Select 0%
15%19327,1007032,604,517 company$21,4701081
Anrok anrok.com7%663,6004312,295$1,852855
Zoho zoho.com
Zoho Books 5%
5%32627,1002681,216,894 company$51,031119
Zamp zamp.com4%322,90026224,260$5888
Stripe parent site
Stripe Tax 2%
2%79823,000102,741
Kintsugi trykintsugi.com2%2490,5003,21938,197$1,35963
Shopify shopify.com
Shopify Tax 2%
2%121,000,00038,0673,486,997 company$3,351110
Quaderno quaderno.io0%307202362,20306

Google's top ten for the three searches hold 15 sites; 5 of them are among the sites the models cited here (avalara.com, tax.thomsonreuters.com, taxcloud.com, taxjar.com, wolterskluwer.com). The first result for “best sales tax compliance software” is avalara.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.
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ModelDirect“What is the best sales tax compliance software for a small B2B company?”Paraphrase“Which sales tax calculation and filing tool would you recommend to a small business that sells to other businesses?”Comparative“What are the top sales tax tools for a small team and how do they differ?”Budget-constrained“What is the best sales tax compliance software for a small company with a tight budget?”Scale-constrained“We are a 30 person company evaluating a sales tax compliance software. What should we look at?”Negative“Which sales tax tools should a small business avoid or be cautious about?”
Claude Haiku 4.5Kintsugi
Five alternativesQuaderno, QuickBooks Sales Tax, Sphere, TaxCloud, TaxJar
ZampChanged
Six alternativesAnrok, Avalara AvaTax, TaxCloud, TaxJar, Thomson Reuters ONESOURCE, Vertex
no first choice
Six alternativesAnrok, Numeral, Quaderno, TaxCloud, TaxJar, Zamp
TaxCloud
Three alternativesQuaderno, QuickBooks Sales Tax, TaxJar
no first choiceagainst: Avalara AvaTax, Numeral, TaxJar, Vertex
GPT-5.4 miniAvalara AvaTax
One alternativeTaxJar
Avalara AvaTaxHeld
One alternativeTaxJar
TaxJar
Two alternativesStripe Tax, TaxCloud
against: Avalara AvaTax, Vertex
TaxJar
One alternativeTaxCloud
against: Avalara AvaTax
no first choicenothing named
Gemini 3.5 FlashAnrok
Six alternativesKintsugi, Prophit.ai, Stripe Tax, TaxCloud, TaxValet, Taxwire
against: Avalara AvaTax
AnrokHeld
Three alternativesAvalara AvaTax, Stripe Tax, TaxCloud
Stripe Tax
Five alternativesAnrok, Lemon Squeezy, Numeral, Paddle, TaxCloud
Shopify Tax
Five alternativesKintsugi, Numeral, Stripe Tax, TaxCloud, Zamp
against: Avalara AvaTax, Vertex
Anrok
Seven alternativesLemon Squeezy, Paddle, Stripe Tax, TaxCloud, TaxJar, TaxValet, Zamp
against: Avalara AvaTax, Sovos, TaxCloud, TaxJar, Thomson Reuters ONESOURCE, Vertex
Perplexity SonarTaxJar
Two alternativesTaxCloud, Zamp
against: Avalara AvaTax
TaxCloudChanged
Two alternativesAvalara AvaTax, CCH SureTax
TaxJar
Five alternativesAvalara AvaTax, DAVO, TaxCloud, Zamp, Zoho Books
TaxJar
Two alternativesTaxCloud, Zoho Books
no first choicenothing named
Grok 4.1 FastTaxJar
Two alternativesStripe Tax, TaxCloud
against: Avalara AvaTax, Vertex
TaxJarHeld
One alternativeAvalara AvaTax
against: Vertex
TaxJar
Two alternativesStripe Tax, TaxCloud
against: Avalara AvaTax
TaxCloud
Two alternativesStripe Tax, TaxJar
against: Avalara AvaTax, Sovos, Vertex
no first choiceagainst: Avalara AvaTax, Sovos, TaxJar, Vertex
Mistral SmallZoho Books
Two alternativesNumeral, TaxJar
against: Vertex
Avalara AvaTax, TaxJarChanged
One alternativeStripe Tax
TaxCloud, TaxJar
Three alternativesAnrok, Stripe Tax, Zoho Books
against: Sovos
TaxCloud, TaxJar
One alternativeAvalara Select
no first choiceagainst: Avalara AvaTax, TaxCloud
DeepSeek V4 FlashAvalara AvaTax
One alternativeTaxJar
against: CCH SureTax, Vertex
ZampChanged
One alternativeTaxCloud
against: Avalara AvaTax, TaxJar
TaxJar
Three alternativesQuickBooks Online, TaxCloud, Zoho Books
against: Avalara AvaTax
TaxCloud
One alternativeTaxJar
against: Avalara AvaTax
TaxJar
Two alternativesAvalara AvaTax, Quaderno
against: Vertex
against: Avalara AvaTax, Kintsugi, Numeral, Sovos, Vertex
Llama 4 MaverickTaxJar
Two alternativesStripe Tax, TaxCloud
Avalara AvaTaxChangedno first choiceTaxCloudno first choicenothing named
Qwen 3.7 FlashTaxJar
One alternativeTaxCloud
against: Avalara AvaTax, Vertex
TaxJarHeld
Three alternativesAvalara AvaTax, Stream, TaxCloud
TaxCloud, TaxJar
One alternativeStripe Tax
against: Avalara AvaTax
TaxCloud, Zoho Books
Two alternativesAvalara Select, TaxJar
no first choice
Two alternativesSimba Tax, TaxJar
against: Avalara AvaTax
against: Avalara AvaTax, Spreadsheets, Thomson Reuters ONESOURCE, Vertex
Kimi K2TaxCloud, TaxJar
Two alternativesAnrok, Zoho Books
against: Avalara AvaTax, Vertex
TaxCloudChanged
One alternativeTaxJar
against: Avalara AvaTax, Thomson Reuters ONESOURCE, Vertex
TaxCloud, TaxJar
One alternativeQuaderno
against: Avalara AvaTax, Vertex
TaxJar
Two alternativesTaxCloud, Zoho Books
against: Avalara AvaTax
TaxCloud
Three alternativesAvalara AvaTax, Stripe Tax, TaxJar
against: Avalara AvaTax, TaxCloud, TaxJar
GLM 4.7 FlashXStripe Tax, TaxJar
Two alternativesQuaderno, TaxCloud
against: Avalara AvaTax
Avalara AvaTaxChanged
One alternativeTaxJar
TaxJar
Three alternativesCCH SureTax, Quaderno, Stripe Tax
against: Avalara AvaTax, Taxwire, Vertex
TaxCloud
Five alternativesNumeral, QuickBooks Sales Tax, Stripe Tax, TaxJar, Xero Tax
no first choiceagainst: Anrok, Avalara AvaTax, Vertex
MiniMax M2.5TaxJar, Zoho Booksagainst: Avalara AvaTaxTaxJarChanged
Three alternativesAnrok, TaxCloud, Zoho Books
TaxCloud, TaxJar
One alternativeAvalara AvaTax
against: Vertex
TaxCloud
Three alternativesKintsugi, Numeral, TaxJar
no first choicenothing named
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. 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-4-5-202510012026-10-01 08:45yes98 s
Direct recommendationGPT-5.4 minigpt-5.4-mini-2026-03-172026-10-01 08:16yes46 s
Direct recommendationGemini 3.5 Flashgemini-3.5-flash2026-10-01 07:38yes2122 s
Direct recommendationPerplexity Sonarsonar2026-10-01 08:28yes204 s
Direct recommendationGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-10-01 09:43yes1910 s
Direct recommendationMistral Smallmistral/mistral-small via mistral2026-10-01 11:06yes137 s
Direct recommendationDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-10-01 08:23yes2225 s
Direct recommendationLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-10-01 08:22yes52 s
Direct recommendationQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-10-01 10:29yes851 s
Direct recommendationKimi K2moonshotai/kimi-k2 via novita2026-10-01 08:03yes1327 s
Direct recommendationGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-10-01 11:25yes1945 s
Direct recommendationMiniMax M2.5minimax/minimax-m2.5 via minimax2026-10-01 08:38yes924 s
ParaphraseClaude Haiku 4.5claude-haiku-4-5-202510012026-10-01 08:50yes97 s
ParaphraseGPT-5.4 minigpt-5.4-mini-2026-03-172026-10-01 09:57yes25 s
ParaphraseGemini 3.5 Flashgemini-3.5-flash2026-10-01 08:51yes1622 s
ParaphrasePerplexity Sonarsonar2026-10-01 09:05yes194 s
ParaphraseGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-10-01 11:15yes229 s
ParaphraseMistral Smallmistral/mistral-small via mistral2026-10-01 08:49yes523 s
ParaphraseDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-10-01 10:09yes2227 s
ParaphraseLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-10-01 09:18yes52 s
ParaphraseQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-10-01 08:08no029 s
ParaphraseKimi K2moonshotai/kimi-k2 via novita2026-10-01 09:59yes1826 s
ParaphraseGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-10-01 10:44yes19213 s
ParaphraseMiniMax M2.5minimax/minimax-m2.5 via minimax2026-10-01 11:25yes1242 s
ComparativeClaude Haiku 4.5claude-haiku-4-5-202510012026-10-01 07:44yes98 s
ComparativeGPT-5.4 minigpt-5.4-mini-2026-03-172026-10-01 09:06yes48 s
ComparativeGemini 3.5 Flashgemini-3.5-flash2026-10-01 08:29yes1527 s
ComparativePerplexity Sonarsonar2026-10-01 07:37yes184 s
ComparativeGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-10-01 10:40yes219 s
ComparativeMistral Smallmistral/mistral-small via mistral2026-10-01 10:59yes99 s
ComparativeDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-10-01 11:11yes2144 s
ComparativeLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-10-01 11:18yes82 s
ComparativeQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-10-01 07:58yes831 s
ComparativeKimi K2moonshotai/kimi-k2 via novita2026-10-01 08:19yes1625 s
ComparativeGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-10-01 09:49yes2429 s
ComparativeMiniMax M2.5minimax/minimax-m2.5 via minimax2026-10-01 11:17yes1219 s
Budget constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-10-01 09:25yes96 s
Budget constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-10-01 09:23yes34 s
Budget constrainedGemini 3.5 Flashgemini-3.5-flash2026-10-01 08:25yes2226 s
Budget constrainedPerplexity Sonarsonar2026-10-01 11:03yes203 s
Budget constrainedGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-10-01 08:37yes219 s
Budget constrainedMistral Smallmistral/mistral-small via mistral2026-10-01 07:55yes95 s
Budget constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-10-01 08:09yes2138 s
Budget constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-10-01 10:32yes52 s
Budget constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-10-01 08:22yes1019 s
Budget constrainedKimi K2moonshotai/kimi-k2 via novita2026-10-01 08:39yes1520 s
Budget constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-10-01 10:13yes1423 s
Budget constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-10-01 10:03yes1325 s
Scale constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-10-01 08:32no06 s
Scale constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-10-01 09:33no07 s
Scale constrainedGemini 3.5 Flashgemini-3.5-flash2026-10-01 08:22yes1024 s
Scale constrainedPerplexity Sonarsonar2026-10-01 08:31yes205 s
Scale constrainedGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-10-01 09:11yes148 s
Scale constrainedMistral Smallmistral/mistral-small via mistral2026-10-01 10:36no06 s
Scale constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-10-01 09:33yes1532 s
Scale constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-10-01 09:28yes52 s
Scale constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-10-01 11:27no027 s
Scale constrainedKimi K2moonshotai/kimi-k2 via novita2026-10-01 08:10yes919 s
Scale constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-10-01 08:40yes1114 s
Scale constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-10-01 10:30yes515 s
Negative framingClaude Haiku 4.5claude-haiku-4-5-202510012026-10-01 09:46yes188 s
Negative framingGPT-5.4 minigpt-5.4-mini-2026-03-172026-10-01 09:15yes45 s
Negative framingGemini 3.5 Flashgemini-3.5-flash2026-10-01 10:24yes1323 s
Negative framingPerplexity Sonarsonar2026-10-01 11:21yes164 s
Negative framingGrok 4.1 Fastspacexai/grok-4.1-fast-non-reasoning via vertex2026-10-01 09:37yes218 s
Negative framingMistral Smallmistral/mistral-small via mistral2026-10-01 08:39yes146 s
Negative framingDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-10-01 09:17yes2438 s
Negative framingLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-10-01 08:59yes53 s
Negative framingQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-10-01 08:17yes1157 s
Negative framingKimi K2moonshotai/kimi-k2 via novita2026-10-01 09:17yes2431 s
Negative framingGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-10-01 07:43yes2023 s
Negative framingMiniMax M2.5minimax/minimax-m2.5 via minimax2026-10-01 08:21yes1932 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 Avalara AvaTax
Avalara (AvaTax + CertCapture) read as Avalara AvaTax
Avalara (AvaTax + Exemption Certificate Management) read as Avalara AvaTax
Avalara (AvaTax) read as Avalara AvaTax
Avalara (Avalara Select / AvaTax) read as Avalara AvaTax
Avalara (Avatax) read as Avalara AvaTax
Avalara (especially AvaTax) read as Avalara AvaTax
Avalara (now part of Sage) read as Avalara AvaTax
ONESOURCE read as Thomson Reuters ONESOURCE
Shopify read as Shopify Tax
Stripe read as Stripe Tax
Unresolved, counted raw
ACTSOLV
EXEMPTAX
Simba Tax
Stream (formerly Taxify)
Discontinued, still offered
No shut-down product was recommended here.
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