Windmill

Windmill

AI-native platform automating performance reviews

Overview

Windmill offers an AI-native performance management platform that automates performance reviews by collecting context from daily work across tools like Slack, GitHub, Jira, Asana, and Google Workspace via an AI agent named Windy. It uses conversations and peer feedback to generate self-reviews and structured manager drafts, and includes Smart 1:1s that auto-create coaching-focused meeting agendas. The system builds a continuous context graph from 1:1s, project work, and feedback to reduce review time and improve engagement. Its goal is to scale personalized management for organizations and expand through seed funding.

About Windmill

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

Industries

Data & Analytics

Enterprise Software

AI & Machine Learning

Company Size

11-50

Company Stage

Seed

Total Funding

$12M

Headquarters

New York City, New York

Founded

2018

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Simplify's Take

What believers are saying

  • On April 28, 2026, Windmill raised $12 million led by Inspired Capital.
  • Windmill said it surpassed 100 customers, including Kalshi, Rho, and Merge, after November 2025 launch.
  • Updated July 21, 2026, Windmill markets free access for ten users, easing trials.

What critics are saying

  • Lattice, Leapsome, Betterworks, and Culture Amp already own performance-management budgets.
  • HR buyers distrust workplace surveillance; Windmill’s Slack and GitHub ingestion amplifies privacy objections.
  • If reviews stay annual, incumbents bundle AI faster and compress Windmill’s category before 2028.

What makes Windmill unique

  • Windmill’s context graph ties reviews to Slack, GitHub, Jira, and Google Workspace evidence.
  • Windy automates self-reviews and manager drafts, cutting review cycles 90%.
  • Founded in 2023 by Yext veterans Max Shaw and Brian Distelburger, it knows enterprise workflows.

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Funding

Total Funding

$12M

Above

Industry Average

Funded Over

1 Rounds

Seed funding is usually the first official round after pre-seed, when a startup has a prototype or concept. It’s typically used to develop the product, test the market, and start building the team. Investors here are often angel investors or early-stage venture capitalists.
Seed Funding Comparison
Above Average

Industry standards

$3.3M
$2M
Netflix
$2.3M
Instacart
$3M
Robinhood
$12M
Windmill

Benefits

Health Insurance

Unlimited Paid Time Off

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

-3%

1 year growth

-3%

2 year growth

-3%
PR Newswire
Apr 28th, 2026
Windmill, the AI Company That Bets on Humans, Raises $12M

/PRNewswire/ -- While the AI industry is racing to replace people, Windmill is building the technology to make them irreplaceable....

Windmill
Apr 28th, 2026
Windmill, the AI company that bets on humans, raises $12M.

Windmill, the AI company that bets on humans, raises $12M. Inspired Capital leads the seed round for the company building the context graph for your people - an AI-native system built on a simple bet: the biggest workforce transformation in a generation is a people problem, and HR is the function best equipped to lead it. - April 28, 2026 NEW YORK - April 28, 2026 - While the AI industry is racing to replace people, Windmill is building the technology to make them irreplaceable. Windmill, the context graph for your people, today announced an $12M fundraise led by Inspired Capital, with participation from Primary Venture Partners, Founder Collective, and Oceans Ventures. The company has grown to over 100 customers including Kalshi, Rho, and Merge, since launching their performance reviews product in November 2025. "There's no question that AI tools will transform how we all work," said Max Shaw, CEO and co-founder at Windmill. "We're building the infrastructure to make sure that the people don't get left behind, by giving companies tools to support their people, not replace them" Why people matter more, not less in the age of AI. Every company in the world is being restructured around AI. Management layers are disappearing, roles are merging, and entire functions are being redefined by what AI can now do. As AI gives individuals leverage that used to require entire teams, the value of each person is going up. Every employee is doing more complex, creative, higher-judgment work. Companies are now tasked with managing capability, potential, and the uniquely human skills that AI makes more important by the day. "I've had upwards of 10,000 people come through companies I've run," said Brian Distelburger, co-founder at Windmill. "Talk to any executive and they'll talk about how important people are. When you drill down a few levels into what they're doing to make sure they have the right people, in the right roles, working on the right things, there's not much depth there." But most companies have no system for understanding any of it. The knowledge of who's doing what, who's growing, who's underutilized, who elevates the people around them - that lives in the heads of a handful of managers and nowhere else. It's lossy, biased, and impossible to act on at scale. You can't ask an AI agent to identify your highest-performing teams, surface bottlenecks, or help you staff the right people on a critical project, because the context doesn't exist. Companies have a system of record for every asset except the one that matters most. "Every headline right now is about AI replacing workers. We think that's the wrong bet. The best organizations of the next decade won't be the ones that eliminate the most headcount. They'll be the ones that use AI to build workforces that are continuously supported and developed. Doing so requires new infrastructure, and that's exactly what Windmill is building. Max, Brian, and Mark have the conviction and the depth to go after this problem the right way, and we're proud to be on the journey with them." - Alexa von Tobel, Managing Partner, Inspired Capital HR's moment. There's a function that understands org design, talent development, change management, and culture better than anyone else in the building. The AI transformation just handed HR the most strategic mandate in the company: lead the people side of the biggest workforce shift in a generation. As organizations get flatter and faster, the strategic adjustments companies used to make annually now need to happen more frequently. That means having the right people in the right roles, operating effectively in your specific environment, has never mattered more, and has never been harder to get right. What Windmill is building. Windmill started with one of the most broken processes in the workplace: performance reviews. It rebuilt the review process to match how modern companies actually work. The platform integrates with Slack, GitHub, Google Workspace, and 30+ other tools where work already happens, so reviews never start from a blank page and are completed 90% faster with 93% employee satisfaction. AI Performance reviews are just the first proof point. Underneath them is what Windmill calls the context graph - a continuously updated, cited understanding of the workforce: * People - who they are and how they connect * Evidence - what actually happened * Expectations - what good looks like * Perspectives - what people think Every insight traces back to a specific Slack thread, pull request, or piece of documentation. "At most companies, the most important context about work and people isn't captured in one place," said Shaw. "It's scattered across apps, notes, conversations, and in the minds of managers. That makes important decisions about people far too dependent on memory and intuition alone. And if you want agents anywhere near those decisions, you first need a systematic way to organize the underlying context. We're building that layer." The context graph is accessible through Windy, Windmill's AI agent, the Windmill web app, and full MCP and API support, making context about your people available wherever a company needs it. About Windmill. Windmill is the context graph for your people. A continuous, cited understanding of your workforce that enables HR to lead strategically, managers to see their teams clearly, and every person's work to speak for itself. It starts with performance reviews that write themselves. Free for up to 10 users. Learn more at gowindmill.com.

PR Newswire
Oct 8th, 2024
Windmill, The Leading Brand in Modern Air Care, Launches Sleek, High-Performance Air Purifier

/PRNewswire/ -- Windmill, the high-performance air care brand best known for modernizing the window air conditioner, today announces the launch of its latest...

AlleyWatch
Oct 8th, 2024
The AlleyWatch Startup Daily Funding Report: 10/8/2024

Tildei, a conversational marketing platform built specifically for social channels, has raised $6M in Seed funding led by Susa Ventures.

Happi
Oct 8th, 2024
Windmill Launches High-Performance Air Purifier, Raises $5 Million in Series A Financing

In tandem with the launch, Windmill has closed a $5M Series A funding round, backed by YETI CapitaI, Pentland Ventures, Dot Capital, SuperAngel Fund and other investors.

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