AI Compliance Startup Dili Lands $21.7M as Infrastructure Projects Face Regulatory Complexity

The AI-powered infrastructure boom is creating mountains of data centers and power plants—but keeping those projects compliant with federal rules is becoming its own challenge. Dili, a software startup focused on AI-driven compliance for construction projects, is betting it can solve that problem at scale.

The company announced a $15 million Series A round on Thursday, led by Khosla Ventures and joined by Allianz, Rebel Fund, and Y Combinator's Garry Tan, among others. Combined with a prior seed round of $6.7 million, Dili has now raised $21.7 million.

The Compliance Maze#

Infrastructure projects—especially those involving federal funding—operate within a tangle of overlapping rules that can trip up even diligent operators. According to CEO Anand Chaturvedi, a single compliance misstep can cost millions in fines.

The regulations span multiple domains:

• Davis-Bacon rules let the Department of Labor set prevailing wage requirements for certain projects
• PWA rules govern wages and apprenticeships for clean energy projects funded under the Inflation Reduction Act
• OSHA and EPA standards apply depending on project type

This complexity means traditional compliance review—often a manual, data-sampling process—leaves room for expensive errors.

How Dili Works#

Rather than rely on AI to make final compliance decisions, Dili uses a hybrid architecture that limits the risk of AI hallucinations. Large language models handle the initial heavy lifting: they ingest unstructured documents from contractors, vendors, payroll systems, and ERP platforms and convert them into structured data. From there, a deterministic system applies the firm, unchanging compliance rules.

The result is speed without sacrificing accuracy. What once demanded a full day of manual review can now be completed in minutes, Chaturvedi said.

Market Traction and Future Shift#

Dili is already operating across roughly 700 active projects, ranging from manufacturing plants to data centers. The company currently serves customers in two ways: some deploy it as internal software, while others outsource compliance work entirely to Dili as a contractor. That split is roughly 50-50 today, but Chaturvedi expects the balance to shift toward in-house adoption as companies internalize compliance workflows.

"Software and AI are going to start eating a lot of those professional services workflows," Chaturvedi noted, signaling that the infrastructure industry may gradually move compliance from specialized consultants to software-driven operations in-house.