-62%

est. 2Y upside i

Sales & MarketingSeries B

Chili Piper is a suite of automated scheduling tools that helps sales teams automatically schedule appointments with leads.

Rank

#2635

Sector

B2B SaaS / Revenue Operations

Est. Liquidity

~3Y

Data Quality

Data: Medium

Chili Piper is capital efficient ($43M ARR on $58M raised) with a unique unified routing+scheduling+chat product. 20% growth is moderate but defensible niche.

Last updated: March 21, 2026

Bull (25%)+100%

Chat AI drives NRR >130%. $80M+ ARR. Acquired at 10-12x.

Base (50%)+35%

$55-65M ARR. Niche leader. Acquired at 8-10x (~$440-650M). Flat to modest.

Bear (25%)-35%

Salesforce builds native; Calendly wins enterprise. Growth stalls.

Est. time to liquidity~3.0 years

Preference Stack Risk

low

Funding Intensity

9%

$58M raised on $625M = 9.3% intensity. Very clean.

Dilution Risk

low

Capital efficient; no dilutive pressure.

Secondary Liquidity

none

No secondary.

General & Administrative — 1 role

Partnerships — 1 role

Research & Development — 1 role

View all 8 open roles at Chili Piper →

Last updated: March 10, 2026

Questions to Ask at the Interview

Strategic questions based on Chili Piper's data — designed to show you've done your homework.

  • 1

    “Chat AI adoption and NRR impact?”

  • 2

    “Salesforce native competition risk?”

  • 3

    “M&A or IPO path?”

Community

Valuation Sentiment

Our model estimates -62% upside. What do you think?

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Disclaimer: This analysis is AI-generated and does not constitute financial or career advice. Always conduct your own due diligence.