Chili Piper

Chili Piper

Automates meeting scheduling for revenue teams

Overview

Chili Piper provides Meeting Lifecycle Automation for revenue teams, focusing on speeding up how inbound meetings are scheduled and managed. The platform offers instant booking, booking links, and calendar integrations so leads can book meetings quickly and routes them to the right sales rep. It works by integrating with calendars and CRMs, using booking links or embedded scheduling flows, automatically selecting the first available times, and coordinating the right rep and meeting details through the pipeline. This differentiates Chili Piper from competitors by its emphasis on end-to-end meeting workflows and seamless CRM/calendar connectivity, designed to cut scheduling time and improve conversion. The company’s goal is to help sales and marketing teams convert more inbound inquiries into booked meetings and, ultimately, close more deals by saving time spent on scheduling.

About Chili Piper

Simplify's Rating
Why Chili Piper is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Enterprise Software

Company Size

201-500

Company Stage

Series B

Total Funding

$54.4M

Headquarters

New York City, New York

Founded

2016

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Simplify's Take

What believers are saying

  • August 2026 enterprise edition signals upmarket expansion beyond core SMB scheduling.
  • G2 partnership and UNBOUND dinners in September 2026 keep Chili Piper visible to buyers.
  • 2026 platform pricing bundles routing, chat, and scheduling into larger ACV contracts.

What critics are saying

  • Calendly launched Callie and Notetaker on August 19 2026, attacking Chili Piper's core workflow.
  • No funding since April 2021 leaves Chili Piper exposed if enterprise conversion stalls.
  • If Calendly and HubSpot commoditize routing, Chili Piper becomes a feature, not a company.

What makes Chili Piper unique

  • Chili Piper's 2026 MCP server exposes live routing and booking to Claude and Codex.
  • Its booking flow routes Salesforce objects instantly, including custom Leads, Contacts, Opportunities, Cases.
  • Chili Piper still targets revenue teams, not generic scheduling, with form-to-meeting workflows.

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Funding

Total Funding

$54.4M

Meets

Industry Average

Funded Over

4 Rounds

Notable Investors:
Series B funding is typically for startups that have proven their business model and need more funding to expand rapidly—often by entering new markets or adding more products. Investors are usually venture capital firms that specialize in later-stage investments.
Series B Funding Comparison
Meet Average

Industry standards

$35M
$33M
Chili Piper
$45M
Linktree
$65M
Substack
$100M
ClickUp

Benefits

Unlimited Paid Time Off

Health Insurance

Dental Insurance

Vision Insurance

Professional Development Budget

Stock Options

Company Social Events

Remote Work Options

Growth & Insights and Company News

Headcount

6 month growth

↓ -1%

1 year growth

↓ -1%

2 year growth

↓ -1%
Exclaimer
Dec 6th, 2024
Simplify meeting bookings with new Chili Piper integration

It's with this in mind that Exclaimer Group is excited to announce its new integration with the leading demand conversion platform, Chili Piper.

PR Newswire
Jun 20th, 2024
Chili Piper spices up its brand & continues its partnership with Veza Digital with a bold brand refresh

Chili Piper spices up its brand & continues its partnership with Veza Digital with a bold brand refresh.

Salesroom
Dec 20th, 2022
Alina Vandenberghe is the Co-founder of Chili Piper

In 2021, Chili Piper received a $33 million dollar investment led by Tiger Ventures at close to a $1 billion dollar valuation.

Rally UXR
Sep 12th, 2022
Chili Piper, Inc. hires Taylor Jennings as Senior UX Researcher

Before Taylor Jennings joined Chili Piper as a Senior UX Researcher and their first research hire, the product team was handling research.

GlobeNewswire
Aug 24th, 2022
Chili Piper Acquires Kosmotime To Build The Next Generation Of Smart Calendars

NEW YORK, Aug. 24, 2022 (GLOBE NEWSWIRE) -- Chili Piper , the leading qualifying, routing & scheduling platform for revenue teams, has acquired KosmoTime , a smart calendar solution helping its users better manage their time

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