September 2026 Edition, published · The permanent record of that edition, superseded since. The current standing is on the category page →
Index › GTM › Sales › Scheduling › Enterprise · September 2026 Edition

Meeting scheduling for enterprise buyers

Asked as “meeting scheduling tool for sales teams”, and as “appointment scheduling software”, on behalf of an enterprise B2B company. 46 first choices recorded across the direct, paraphrase, budget and scale prompts, twelve models each.
Standing · first-choice share
52%
Clear leader
52Calendly20Chili Piper11Microsoft Bookings17others

52% of first choices, clear leader.

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 an enterprise B2B company. Ordered by share.
ProductFirst-choice shareNegative rateLabelsQuadrant
01Calendly52%17%59endorsed leader
02Chili Piper20%21%47accepted challenger
03Microsoft Bookings11%8%26accepted challenger
04Cal.com7%3%32accepted challenger
05HubSpot Meetings4%25%24criticized challenger
06RevenueHero2%8%12accepted challenger
Show the one product at 0%, ordered by negative rate
07Doodle0%67%12criticized 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.
Head to headHead-to-head pages are published for mid-market buyers, so these open on mid-market figures, not enterprise.
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
Accepted challengerEndorsed leader
0%First-choice share → · lines at 30% share and 25% negative70%
Key
01Calendly52%
02Chili Piper20%
03Microsoft Bookings11%
04Cal.com7%
05HubSpot Meetings4%
06RevenueHero2%
07Doodle0%

What they warned about

Three of twelve models held their first choice under the paraphrase. Claude Haiku 4.5, GPT-5.4 mini, Gemini 3.5 Flash, Perplexity Sonar, Grok 4.20, Mistral Small, DeepSeek V4 Flash, Llama 4 Maverick 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.
Chili Piper
21%
10 of 47 labels negative · 10 of 12 models · 5 hard negative
“transitioned to a model that charges a high base platform fee ($15k+/year) plus additional fees... makes financial forecasting difficult” Qwen 3.7 Flash, budget prompt
Doodle
67%
8 of 12 labels negative · 7 of 12 models · 4 hard negative
“"Consumer-First" Polling Tools (e.g., Doodle) ... Why to avoid: These platforms frequently lack Business Associate Agreements (BAAs)” Qwen 3.7 Flash, negative prompt
Calendly
17%
10 of 59 labels negative · 7 of 12 models · 3 hard negative
“What to avoid: Individual, free, or basic paid plans of popular schedulers (e.g., standard Calendly, Doodle...)” Gemini 3.5 Flash, negative prompt
HubSpot Meetings
25%
6 of 24 labels negative · 6 of 12 models
“including standard tiers of Calendly, HubSpot Meetings, and Microsoft Bookings) run background tracking scripts” Gemini 3.5 Flash, negative prompt

What they cite

Four of the twelve models returned a source list in this edition: four return the pages they cited.

Sites the answers cite

22 of 72 answers in this category came back with a source list, from 4 of 12 models: citations where the model returns them, or the search results it consulted. 304 links across 132 sites, every framing counted. Ranked by the number of answers carrying the site or page. The other 8 models searched through a gateway that returned no source list on this edition.

vendor site · Cal.com11 answers · 17 citations · 3 models
vendor site · RevenueHero10 answers · 12 citations · 3 models
vendor site · LeadAngel10 answers · 10 citations · 3 models
vendor site · Calendly9 answers · 16 citations · 3 models
vendor site · Guideflow8 answers · 11 citations · 2 models
vendor site · HubSpot7 answers · 13 citations · 4 models
vendor site · Albato6 answers · 6 citations · 2 models
5 answers · 6 citations · 2 models
vendor site · Cleverly5 answers · 5 citations · 2 models
vendor site · Lunacal5 answers · 5 citations · 2 models
5 answers · 5 citations · 2 models
vendor site · Zapier5 answers · 5 citations · 2 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 meeting scheduling tool for sales teams”, “meeting scheduling tool for sales teams”. 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
Calendly calendly.com52%201368,0002,824292,858$345
Chili Piper chilipiper.com20%2756,6001306,997$29541
Microsoft parent site
Microsoft Bookings 11%, Microsoft Teams 0%
11%952,240,000403,136
Cal.com cal.com7%1332,900100439,94337
HubSpot parent site
HubSpot Meetings 4%, HubSpot Sales Hub 2%
7%687368,0009,776
RevenueHero revenuehero.io2%10472011,1875
Salesforce parent site
Salesforce Sales Cloud 2%, Salesforce Scheduler 0%
2%318550,00060,632
LeadAngel leadangel.com0%1139003690
Google parent site
Google Calendar Appointment Scheduling 0%
0%3612,100138
Reclaim.ai reclaim.ai0%45,4006143,6290

Google's top ten for the two searches hold 17 sites; 5 of them are among the sites the models cited here (blog.hubspot.com, cal.com, cleverly.co, peoplemanagingpeople.com, youcanbook.me). The first result for “best meeting scheduling tool for sales teams” is peoplemanagingpeople.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 meeting scheduling tool for sales teams for an enterprise B2B company?”Paraphrase“Which appointment scheduling software would you recommend to a large B2B company with thousands of employees?”Comparative“What are the top enterprise-grade meeting scheduling tools and how do they differ?”Budget-constrained“What is the best meeting scheduling tool for sales teams for a large company that needs predictable total cost across thousands of users?”Scale-constrained“We are a 5,000 person company with SSO, SOC 2 and procurement review requirements evaluating a meeting scheduling tool for sales teams. What should we look at?”Negative“Which meeting scheduling tools should a large enterprise avoid or be cautious about?”
Claude Haiku 4.5no first choiceCalendlyChanged
Two alternativesCal.com, LeadAngel
Cal.com
Two alternativesCalendly, Chili Piper
Calendly
One alternativeHubSpot Meetings
against: Chili Piper
Calendly
Two alternativesChili Piper, HubSpot Meetings
against: Calendly
GPT-5.4 miniChili Piper
Two alternativesCalendly, Salesloft Meetings
Microsoft BookingsChanged
Two alternativesCalendly, Google Calendar Appointment Scheduling
Chili Piper
Three alternativesDoodle, HubSpot Meetings, Microsoft Bookings
Calendlyagainst: Chili Piper, HubSpot Meetingsno first choiceagainst: Microsoft Bookings
Gemini 3.5 FlashChili Piper, RevenueHero
Three alternativesCal.com, Default, NC Squared
against: Calendly
Calendly, Chili PiperChanged
Two alternativesCal.com, LeanData
Calendly
Five alternativesCal.com, Chili Piper, Google Calendar Appointment Scheduling, Microsoft Bookings, OnceHub
Cal.com, Microsoft Bookings
Two alternativesHubSpot Meetings, Salesforce Scheduler
against: Calendly, Chili Piper
Chili Piper
Three alternativesCal.com, Calendly, LeanData
against: Acuity Scheduling, Calendly, Doodle, HubSpot Meetings, Microsoft Bookings, SimplyBook
Perplexity SonarChili Piper
Four alternativesCal.com, HubSpot Meetings, LeanData BookIt, RevenueHero
CalendlyChanged
Three alternativesChili Piper, LeadAngel, RevenueHero
no first choice
Seven alternativesCal.com, Calendly, Chili Piper, HubSpot Meetings, LeadAngel, Microsoft Bookings, Skedda
HubSpot Meetings
One alternativeChili Piper
no first choiceagainst: Apple Calendar, Chili Piper, Dibsido, Google Calendar Appointment Scheduling, Officely, Outlook
Grok 4.20Chili Piper
One alternativeCalendly
Microsoft BookingsChanged
Two alternativesCalendly, Chili Piper
no first choiceagainst: DoodleCalendly
One alternativeMicrosoft Bookings
against: Chili Piper, HubSpot Meetings, OnceHub
Calendly
Three alternativesCal.com, Chili Piper, OnceHub
against: Acuity Scheduling, SavvyCal
against: Calendly, Doodle, When2meet
Mistral SmallChili Piper
Three alternativesCalendly, HubSpot Meetings, RevenueHero
Microsoft BookingsChanged
Four alternativesCal.com, Engageware Scheduler for Salesforce, LeadAngel, Salesforce Scheduler
Microsoft Teams, Zoom Scheduler, Zoom Webinars
Three alternativesCalendly, Fellow, Monday.com
Calendly
Three alternativesChili Piper, Microsoft Bookings, RevenueHero
no first choiceagainst: Calendly, Doodle, Microsoft Teams scheduling features, WhenAvailable, Zoom Webinars
DeepSeek V4 FlashChili Piper
Four alternativesCalendly, Outreach, Salesloft, ZoomInfo GTM Workspace
Cal.comChanged
Two alternativesChili Piper, OnceHub
against: Calendly
Cal.com, Calendly
Four alternativesChili Piper, Microsoft Bookings, Motion, Reclaim.ai
against: Clockwise
Calendly
One alternativeMicrosoft Bookings
against: Cal.com, Chili Piper, HubSpot Sales Hub, RevenueHero
Calendly
Two alternativesCal.com, Chili Piper
against: HubSpot Meetings
against: Acuity Scheduling, Calendly, Doodle, When2meet
Llama 4 MaverickCalendly
Two alternativesHubSpot Meetings, ZoomInfo GTM Workspace
HubSpot MeetingsChanged
Two alternativesLunacal, Qualified
Cal.com
Two alternativesChili Piper, LeadAngel
HubSpot Sales Hub
Two alternativesCalendly, Chili Piper
no first choicenothing named
Qwen 3.7 FlashCalendly
Two alternativesChili Piper, RevenueHero
CalendlyHeld
Two alternativesChili Piper, Clockwise
Calendly
Four alternativesFellow, Microsoft Bookings, SavvyCal, meetergo
Calendly
Two alternativesHubSpot Sales Hub, Microsoft Dynamics 365 Scheduler / Bookings
against: Chili Piper, OnceHub
no first choiceagainst: Calendly, Doodle
Kimi K2Calendly
Four alternativesChili Piper, HubSpot Meetings, RevenueHero, ZoomInfo GTM Workspace
CalendlyHeld
Three alternativesChili Piper, Microsoft Bookings, Salesforce Scheduler
Calendly
Five alternativesCal.com, Chili Piper, HubSpot Meetings, Microsoft Bookings, Reclaim.ai
against: Clockwise
Calendly
Two alternativesMicrosoft Bookings, RevenueHero
against: Chili Piper
Calendly
Three alternativesCal.com, Chili Piper, Microsoft Bookings
against: SavvyCal
against: Avoma, Basic/Free Calendly, Doodle, Fathom, Fireflies.ai, Google, Grain, HubSpot Meetings, MeetGeek, Microsoft, Otter.ai, Read AI, Sembly, Zoom Webinars
GLM 4.7 FlashXCalendly
Three alternatives11x, Cal.com, Chili Piper
CalendlyHeld
Two alternativesCal.com, Chili Piper
Calendly
Four alternativesCal.com, Chili Piper, Doodle, Microsoft Bookings
Calendly
One alternativeMicrosoft Bookings
against: Chili Piper
no first choiceagainst: Deskbird, Dibsido, Envoy Workplace, MeetingRoomApp, OfficeRnD, OfficeSpace, Officely, Robin, SuperSaaS, Tactic, WorkInSync, YAROOMS
MiniMax M2.5Calendly, Chili Piper
Three alternativesCirrus Insight, HubSpot Meetings, RevenueHero
Calendly, Salesforce Sales CloudChanged
Four alternativesHubSpot Sales Hub, Rippling, UKG Ready, Zoom Workplace
Calendly, Google Calendar Appointment Scheduling, Microsoft Outlook Calendar
Three alternativesMotion, Reclaim.ai, Sunsama
Microsoft Bookings
Three alternativesCal.com, Calendly, Lark
against: Chili Piper, HubSpot Meetings
Cal.com
Two alternativesCalendly, HubSpot Meetings
against: Calendly, Doodle, Zoom Free Tier
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-4-5-202510012026-09-15 04:08no04 s
Direct recommendationGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-15 02:45yes34 s
Direct recommendationGemini 3.5 Flashgemini-3.5-flash2026-09-14 23:44yes1624 s
Direct recommendationPerplexity Sonarsonar2026-09-15 00:38yes206 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)2026-09-15 01:56yes010 s
Direct recommendationMistral Smallmistral/mistral-small via mistral2026-09-14 23:07yes08 s
Direct recommendationDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-09-15 04:49yes034 s
Direct recommendationLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-15 04:26yes03 s
Direct recommendationQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-15 03:42yes047 s
Direct recommendationKimi K2moonshotai/kimi-k2 via novita2026-09-15 02:19yes068 s
Direct recommendationGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-15 02:39yes062 s
Direct recommendationMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-14 23:52yes017 s
ParaphraseClaude Haiku 4.5claude-haiku-4-5-202510012026-09-14 23:43yes1515 s
ParaphraseGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-15 03:02yes35 s
ParaphraseGemini 3.5 Flashgemini-3.5-flash2026-09-15 03:01yes1119 s
ParaphrasePerplexity Sonarsonar2026-09-15 02:06yes206 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)2026-09-14 23:44yes08 s
ParaphraseMistral Smallmistral/mistral-small via mistral2026-09-15 00:09yes08 s
ParaphraseDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-09-15 02:24yes066 s
ParaphraseLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-15 04:19yes02 s
ParaphraseQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-15 03:23yes049 s
ParaphraseKimi K2moonshotai/kimi-k2 via novita2026-09-15 03:38yes031 s
ParaphraseGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-15 01:17yes0113 s
ParaphraseMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-15 03:31yes041 s
ComparativeClaude Haiku 4.5claude-haiku-4-5-202510012026-09-15 04:55yes1111 s
ComparativeGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-14 23:52yes36 s
ComparativeGemini 3.5 Flashgemini-3.5-flash2026-09-15 00:01yes2025 s
ComparativePerplexity Sonarsonar2026-09-15 03:20yes208 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)2026-09-15 03:19yes09 s
ComparativeMistral Smallmistral/mistral-small via mistral2026-09-15 02:43yes06 s
ComparativeDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-15 02:47yes021 s
ComparativeLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-15 03:22yes02 s
ComparativeQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-15 02:49yes030 s
ComparativeKimi K2moonshotai/kimi-k2 via novita2026-09-14 23:22yes033 s
ComparativeGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-15 01:53yes035 s
ComparativeMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-14 23:09yes013 s
Budget constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-15 04:58yes179 s
Budget constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-15 03:51yes44 s
Budget constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-14 23:11yes2725 s
Budget constrainedPerplexity Sonarsonar2026-09-14 23:30yes196 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)2026-09-15 00:24yes09 s
Budget constrainedMistral Smallmistral/mistral-small via mistral2026-09-15 02:29yes08 s
Budget constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-09-15 01:34yes051 s
Budget constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-15 03:50yes02 s
Budget constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-15 03:47yes045 s
Budget constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-15 02:08yes044 s
Budget constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-15 03:59yes087 s
Budget constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-15 00:36yes091 s
Scale constrainedClaude Haiku 4.5claude-haiku-4-5-202510012026-09-15 01:15yes1616 s
Scale constrainedGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-14 23:21yes414 s
Scale constrainedGemini 3.5 Flashgemini-3.5-flash2026-09-14 23:21no016 s
Scale constrainedPerplexity Sonarsonar2026-09-14 22:55yes209 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)2026-09-15 02:32yes010 s
Scale constrainedMistral Smallmistral/mistral-small via mistral2026-09-15 00:36no05 s
Scale constrainedDeepSeek V4 Flashdeepseek/deepseek-v4-flash via fireworks2026-09-14 23:00yes021 s
Scale constrainedLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-15 01:55yes03 s
Scale constrainedQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-14 23:24no033 s
Scale constrainedKimi K2moonshotai/kimi-k2 via novita2026-09-14 23:30yes053 s
Scale constrainedGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-14 23:17yes069 s
Scale constrainedMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-15 02:26yes018 s
Negative framingClaude Haiku 4.5claude-haiku-4-5-202510012026-09-15 03:44yes149 s
Negative framingGPT-5.4 minigpt-5.4-mini-2026-03-172026-09-15 04:19yes310 s
Negative framingGemini 3.5 Flashgemini-3.5-flash2026-09-14 23:00yes1823 s
Negative framingPerplexity Sonarsonar2026-09-14 23:05yes207 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)2026-09-15 03:45yes08 s
Negative framingMistral Smallmistral/mistral-small via mistral2026-09-14 23:01yes07 s
Negative framingDeepSeek V4 Flashdeepseek/deepseek-v4-flash via deepinfra2026-09-15 01:22yes078 s
Negative framingLlama 4 Maverickmeta/llama-4-maverick via bedrock2026-09-15 02:41yes02 s
Negative framingQwen 3.7 Flashalibaba/qwen3.7-flash via alibaba2026-09-15 02:57yes080 s
Negative framingKimi K2moonshotai/kimi-k2 via novita2026-09-15 04:19yes077 s
Negative framingGLM 4.7 FlashXzai/glm-4.7-flashx via zai2026-09-15 03:03yes044 s
Negative framingMiniMax M2.5minimax/minimax-m2.5 via minimax2026-09-15 02:54yes013 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
Acuity read as Acuity Scheduling
Google Calendar read as Google Calendar Appointment Scheduling
Google Calendar (Google Workspace) read as Google Calendar Appointment Scheduling
Google Calendar Appointment Schedules read as Google Calendar Appointment Scheduling
Google Calendar Appointment Slots read as Google Calendar Appointment Scheduling
Google Calendar native scheduling read as Google Calendar Appointment Scheduling
Google Workspace Calendar read as Google Calendar Appointment Scheduling
Hubspot Meeting read as HubSpot Meetings
Unresolved, counted raw
Accruent EMS
Apple Calendar
Basic/Free Calendly
Calenso
Deputy
Deskbird
Engageware Scheduler for Salesforce
Google
MeetingRoomApp
Microsoft
Microsoft Dynamics 365 Scheduler / Bookings
Microsoft Teams scheduling features
Nextcloud Calendar
OfficeRnD
OfficeSpace
Salesloft Meetings
SimplyBook
Sunsama
Tactic
UKG Ready
WorkInSync
YAROOMS
Zoom Free Tier
Zoom Workplace
Discontinued, still offered
No shut-down product was recommended here.
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