Max Shaw and Brian Distelburger on Reinventing People Management with Windmill

Windmill bets AI makes people management the real bottleneck

Windmill is building the context layer for people management. Its founders argue that as AI agents absorb more of the output, the scarce input becomes knowing who on a team is good at what, and the systems that hold that knowledge, the org chart and the annual review, sit disconnected from where work happens. They sold the idea fast because HR leaders already hate the process they are forced to run.

Takeaways

• AI agents make humans the bottleneck. Brian Distelburger expects agent output to dwarf human output, and because individuals remain accountable for work, people become the constraint on how much gets done. He calls it a civilizational change management problem rather than a tooling one.
• Windmill is a context graph for people. Max Shaw built the system he wanted at Yext. It connects the org chart in the HRIS and the apps where work actually happens, such as Slack and GitHub, so performance reviews stop sitting apart from daily work.
• Performance management depends on manager quality. Reviews run once or twice a year and reflect what managers remember, so the experience varies wildly by team. ICs report too little feedback while HR teams spend most of their time administering process instead of improving it.
• Context moves reviews from annual to continuous. Windmill does not replace the review, it feeds it context. Shaw says cycles will move from annual to continuous, taking days rather than weeks, and the one-on-one product already knows what someone has been working on.
• Traction came fast and the sale was easy. Windmill launched in November 2025 and passed 100 customers. Distelburger calls selling it the easiest process of his career, and 93% of participating employees rated it the best review process they have experienced.
• Managers will carry far more reports. Shaw points to Coinbase saying people will have more direct reports, and warns that managers who struggle with five or six reports will fall apart at 10, 15 or 20 without a new system.

What the founders predict

• Individuals will earn far more. Distelburger expects people to make a lot more money individually, with smaller teams accomplishing more even if companies do not shrink.
• The war for top talent reaches a new level, and org charts may become more circular as roles are shaped around individual strengths.
• Roles and pay grow personalized. Shaw predicts every role gets treated individually, compensation disperses more widely, and AI coaches sit alongside managers around the clock.
• Engineering is the bellwether. Shaw says engineering hiring is going up because each engineer is worth more, and predicts what happened there will hit many other white-collar roles within five years.