HR AI Index

Index › Vendors › Chili Piper · September 2026 Edition

2 categories · Named, not ranked

Chili Piper

15Judge labels

1First choices

1Negative labels

8 of 12Models named it

2Categories

September 2026 Edition. Every number here is derived from the raw labels under vendor table vv2026-09.1, every buyer segment counted.

Standing

4 labels, too few to rank

A product needs 10 labels in a category before a share or quadrant is stated. Chili Piper was named 4 times in Workforce scheduling and 1 other category, where Deputy led with 26%. The labels and the evidence are below, counted exactly.

By buyer segmentRead the same way at every buyer size.

Small business29 of 85

under the label threshold

Mid-market30 of 94

under the label threshold

Enterprise14 of 117

under the label threshold

In workforce scheduling · each standing computed within its segment · bars are 0 to 100 · the accent bar is the product's own best reading

Standing by category

Every category where a model named Chili Piper for a mid-market B2B company. Share is first choices across the direct, paraphrase, budget and scale prompts; rank is within every product named in that category.

Category	Function	Share	Rank	Negative rate	Labels	Quadrant
Workforce scheduling	Core HR and payroll	0%	30 of 94	0%	3	under 10 labels · led by Deputy at 26%
Interview scheduling	Talent acquisition	0%	42 of 72	0%	1	under 10 labels · led by Calendly at 21%

Movement

This is the first edition on this tier, so no move can be computed for Chili Piper yet. From the next edition this section shows, per buyer segment, whether its share moved by more than the measured noise floor.

By model

How each model treated Chili Piper across every prompt where it was named for a mid-market B2B company. Twelve models, six prompts per category.

Model	Alternative	Mention	Labels
Claude Haiku 4.5	0	1	1
GPT-5.4 mini	0	0	0
Gemini 3.5 Flash	1	0	1
Perplexity Sonar	0	0	0
Grok 4.1 Fast	0	0	0
Mistral Small	0	0	0
DeepSeek V4 Flash	0	1	1
Llama 4 Maverick	0	1	1
Qwen 3.7 Flash	0	0	0
Kimi K2	0	0	0
GLM 4.7 FlashX	0	0	0
MiniMax M2.5	0	0	0

By framing

Which of the six questions produced the naming. By model says how often; this says asked what. The first-choice count on the right carries the marks of the models that produced it.

FramingLabels by classFirst choices

Direct4 labels1

Paraphrase1 labelNone

Comparative8 labelsNone

Budget-constrained0 labelsNone

Scale-constrained1 labelNone

Negative1 labelNone

First choiceAlternativeMentionNegative15 labels in all, every segment counted; 1 of the 1 first choices count toward share, since the comparative and negative framings do not. The bar is one segment per label class, to scale within the framing.

What the models said for it

Verbatim evidence the judge attached to positive labels.

“Chili Piper is the industry standard for routing meetings” Gemini 3.5 Flash · Workforce scheduling · direct prompt · alternative

And against it

Verbatim evidence attached to negative labels. A warning on a product with few labels is a warning; on a product with many, it is one voice among them.

No model argued against it.

Named alongside

The products named in the same answers as Chili Piper, over the 15 answers that named it. Took the first choice instead counts the answers where the other product was the first choice and Chili Piper was named but was not.

ProductSame answerTook the first choice insteadHead to head

Calendly14 of 153Not in the top three

Cal.com7 of 150Not in the top three

Acuity Scheduling5 of 150Not in the top three

Resource Guru4 of 151Not in the top three

Shiftboard4 of 151Not in the top three

Microsoft Bookings4 of 150Not in the top three

Deputy3 of 151Not in the top three

GoodTime3 of 151Not in the top three

UKG Pro3 of 151Not in the top three

ActiveBatch3 of 150Not in the top three

A head-to-head page exists where both products are in a category's top three. The other rows are the same fact without a page behind them, so they link to the product instead.

What carried it into the answer

The sites and pages cited by the answers that named Chili Piper. A fact about retrieval, not a lever on the model.

Citations exist only for the models that return a source list, four of the twelve in this edition, so these counts come from 9 of the 15 answers that named Chili Piper and are not a share of its labels.

Domains cited

gitnux.org6

cal.com5

leadangel.com5

youcanbook.me4

aimultiple.com3

calendly.com3

efficient.app3

learn.g2.com3

schedly.io3

sourceforge.net3

Thirty-eight of the thirty-eight domain citations in answers naming Chili Piper came from somebody else's page.

Pages cited

gitnux.org/best/enterprise-appointment-scheduling-software5

leadangel.com/blog/operations/enterprise-scheduling-software5

cal.com/blog/enterprise-scheduling-software4

gitnux.org/best/enterprise-scheduling-software4

aimultiple.com/enterprise-job-scheduler-software3

calendly.com/blog/calendly-vs-chili-piper3

schedly.io/top-7-scheduling-tools-compared-20263

waitwellsoftware.com/resources/articles/best-appointment-scheduling-software3

Pages are listed as the models cited them.

Is this your product?

Claim this page

Claiming is free and changes nothing in the data. A claimed page shows a verified contact who is told when each edition publishes and when Chili Piper's standing changes by more than the noise floor; the right to propose corrections to the vendor table, meaning names the judge wrote that should or should not read as Chili Piper, applied by version and listed in the change log; and a one-line description supplied by the vendor and marked as such.

It does not get any change to labels, shares or verdicts, any preview, or any say over which quotes appear. A verification link goes to your work email; an address at chilipiper.com is approved on the spot, any other address is reviewed by hand.

Your name and company appear on the claimed page, or the company alone if you ask below. A title and a LinkedIn address appear there too if you give them, and are left off if you do not. Your email address is never published.