Windmill Secures $12 Million to Fix How Companies Track People

Windmill, building the context graph for your people, led by Brian Distelburger, Mark Tanner, Max Shaw, and the team, has announced a $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 its performance reviews product in November 2025.

“There’s no question that AI tools will transform how work gets done,” said Max Shaw, CEO and co-founder at Windmill. “The focus is on building infrastructure that ensures people are not left behind, equipping companies with tools that support their workforce rather than replace it.”

Why People Matter More, Not Less, in the Age of AI

AI is reshaping companies, reducing layers and redefining roles. As individuals gain leverage once held by teams, their value rises, with work shifting toward higher-judgment and creative tasks.

“I’ve had upwards of 10,000 people come through companies I’ve run,” said Brian Distelburger. “Leaders talk about people being critical, but systems to manage talent effectively are often shallow.”

Most organizations lack a clear system to understand performance, growth, and impact at scale. As a result, the most important asset, people, remains difficult to measure, manage, and optimize.

“Every headline today focuses on AI replacing workers, but that framing misses the point. The most successful organizations of the next decade will not be those that cut the most headcount, but those that use AI to continuously support and develop their workforce. Achieving this requires new infrastructure, precisely what Windmill is building. Max, Brian, and Mark bring the conviction and depth needed to approach this challenge the right way, and strong confidence underpins this journey alongside them.”

— Alexa von Tobel, Managing Partner, Inspired Capital

HR’s Moment

A function already exists that understands org design, talent development, change management, and culture better than any other: HR. The AI shift has elevated its role into a strategic mandate: leading the people side of a generational workforce transformation.

As organizations become flatter and faster, adjustments once made annually must now happen continuously. Getting the right people into the right roles has become both more critical and more complex.

Legacy tools like annual surveys and spreadsheets are no longer sufficient. Real-time visibility into workforce dynamics is now essential to lead effectively.

What Windmill Is Building

Windmill began by rethinking performance reviews, one of the most broken workplace processes, aligning them with how modern teams operate. By integrating with tools like Slack, GitHub, and Google Workspace, reviews are grounded in real work, completed faster, and with significantly higher satisfaction.

These AI-powered reviews are only the starting point. Beneath them sits the “context graph”, a continuously updated, evidence-backed model of the workforce, capturing people, actions, expectations, and perspectives in one place.

Each insight is tied to real activity, replacing fragmented, memory-driven decisions with structured, traceable context. This layer is accessible through Windy (the AI agent), the web app, and APIs, making workforce intelligence available wherever decisions are made.