+52%

est. 2Y upside i

DevOps & InfraSeries A

Open-source platform to turn scripts into internal apps & workflows

Rank

#1624

Sector

Developer Tools

Est. Liquidity

~5Y

Data Quality

Data: Low

Windmill is a high-risk, high-optionality Series A bet where the upside is real but very hard to size: the company raised only $5M in its October 2024 Series A (total $15M raised) with no disclosed revenue, growth rate, or valuation, and faces intense competition from Retool, Temporal, and cloud providers.

Last updated: May 13, 2026

Bull (12%)+300%

Windmill captures significant enterprise developer-tools spend, scaling to $30-50M ARR by 2028 and attracting a Series C at $300-500M valuation — a 10-15x markup on the estimated ~$30M Series A post-money. The open-source community flywheel accelerates enterprise conversion and the unified script-to-workflow-to-UI platform wins large engineering orgs away from fragmented Retool + Airflow stacks.

Base (53%)+80%

Windmill achieves steady but moderate growth to $8-15M ARR, raises a Series B at roughly $80-120M post-money (~3-4x the estimated $30M Series A valuation), but equity remains illiquid for 5+ years. Dilution from 2 additional funding rounds and $15M of senior liquidation preferences meaningfully compress common-stock returns.

Bear (35%)-75%

Entrenched competitors — Retool, Temporal, Airflow, and cloud-native script runners — squeeze growth, revenue stalls below $3-5M ARR, and Windmill sells in a distressed acqui-hire or shuts down. With $15M in liquidation preferences senior to common stock, employee equity likely returns near zero in any sub-$20M outcome.

Est. time to liquidity~5.0 years

Preference Stack Risk

high

Funding Intensity

43%

With $15M in total liquidation preferences and an estimated post-money Series A valuation of $25-40M, preferred shareholders absorb approximately 38-60% of any exit proceeds before common stock participates.

Dilution Risk

high

A 27-person Series A company will almost certainly require 2-3 additional equity rounds before a liquidity event, each likely diluting existing shareholders by 18-25% per round.

Secondary Liquidity

none

No secondary market activity has been reported; at 27 employees and early stage, tender offers or structured secondaries are extremely unlikely in the near term.

Engineering — 3 roles

View all 3 open roles at Windmill →

Last updated: March 10, 2026

Questions to Ask at the Interview

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

  • 1

    “What is current ARR and net revenue retention, and what does the conversion funnel from open-source self-hosted users to paid cloud or enterprise contracts look like today?”

  • 2

    “How does Windmill plan to defend against Retool's expanding workflow features and Temporal's growing internal-tools ecosystem — what is the durable, defensible moat in three years?”

  • 3

    “What is the fully diluted share count and the most recent 409A strike price for new option grants, and has the board discussed any secondary liquidity or tender-offer program?”

Community

Valuation Sentiment

Our model estimates +52% 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.