AI compliance startup Dili has closed a $15 million Series A round led by Khosla Ventures, with participation from Allianz, Rebel Fund, Darren Bechtel of Brick and Mortar Ventures, and Garry Tan of Y Combinator. The round brings Dili's total capital raised to $21.7 million, inclusive of a prior $6.7 million seed round. TechCrunch

Dili, founded by CEO Anand Chaturvedi and operating at the domain dili.com, builds software that targets compliance workflows for U.S. infrastructure projects, with a particular emphasis on construction initiatives receiving federal funding. As of July 2026, the company's platform is deployed across approximately 700 projects. TechCrunch

The core regulatory burden Dili addresses centers on Prevailing Wage and Apprenticeship (PWA) compliance, a requirement attached to federal construction projects. The platform assists users in complying with Davis-Bacon Act mandates as well as Inflation Reduction Act (IRA) requirements, and it generates IRS-ready compliance reports. Dili PWA

Y Combinator's company directory frames Dili as an AI system of record for physical industries, designed to track compliance, analyze labor and spend, and run payroll. The company's LinkedIn page describes the product as an AI co-pilot that automates due diligence and deal management for tax credits. Y Combinator LinkedIn

Dili was part of Y Combinator's Summer 2023 batch, and YC's Garry Tan participated in the current Series A. TechCrunch Y Combinator

The Series A lead investor brings a particular profile to the round. Vinod Khosla, whose firm led the financing, was ranked No. 10 on the Forbes 250 list of America's Greatest Innovators in 2026. Khosla Ventures

The participation of both Allianz and Brick and Mortar Ventures' Darren Bechtel alongside a deep-tech investor like Khosla Ventures points to the specific cross-section Dili occupies. Federal infrastructure compliance involves intersecting layers of labor law, tax credit administration, and insurance risk, and the cap table here reflects each of those constituencies rather than a single bet on a horizontal AI capability.

The regulatory surface area is genuinely complex. Davis-Bacon Act compliance requires contractors to pay locally prevailing wages on federally funded public works projects, a determination that varies by jurisdiction and trade. The Inflation Reduction Act layered additional PWA requirements on top of certain clean energy projects to unlock enhanced tax credits. For contractors navigating both regimes, the documentation overhead is substantial, and the cost of errors can range from withheld payments to disqualification from federal programs.

Generating IRS-ready compliance reports directly from project and payroll data is the kind of workflow automation where large language models and structured-data extraction can materially reduce manual processing overhead. The system-of-record framing positions Dili not merely as a document generator but as the authoritative data layer against which compliance status is continuously measured, which is a meaningfully different technical and commercial proposition than a point-solution copilot.

Worth flagging is the volume of adoption already on the platform. Seven hundred active projects as of July 2026 suggests the product has moved past early-stage validation into operational use at scale, though the size and complexity of those projects is not specified in the available reporting.

For infrastructure contractors, the practical appeal of an automated compliance layer is straightforward: it compresses the cycle time between work performed, payroll verification, and regulatory submission, reducing the working-capital drag that manual compliance processes introduce. Whether Dili becomes the default system of record for this segment will depend on how effectively it can handle the long tail of jurisdictional variations in prevailing wage determinations, and on whether the platform can maintain audit defensibility as federal agencies refine their own data ingestion and verification processes.