Every construction project drowns in paper. Drawings, specifications, submittals, RFIs, schedules — a mid-size commercial build generates tens of thousands of documents, stored across fragmented systems, rarely cross-referenced, and almost never searchable in the way a project team actually needs.
That problem is the founding thesis of Trunk Tools. The New York-based startup, founded in 2021 by Dr. Sarah Buchner, has now raised a $40 million Series B led by Insight Partners, bringing its total funding to $70 million. Previous backers Redpoint Ventures and Innovation Endeavors participated alongside new investors StepStone, Liberty Mutual Strategic Ventures, and Prudence.
The raise comes roughly eleven months after a $20 million Series A led by Redpoint, and signals accelerating conviction from institutional software investors that the construction document problem is large enough — and hard enough — to justify a dedicated AI platform rather than a feature bolt-on from an incumbent.
What Trunk Tools Actually Builds
The core product is not a search engine, though it behaves like one to users. Trunk Tools ingests the unstructured documents that define a construction project — drawings in PDF, specifications in Word, schedules in P6, submittals from a dozen subcontractors — and transforms them into a structured, queryable knowledge layer.
A superintendent on site can ask “what is the specified concrete mix for the podium level?” in plain English and receive an answer with the source document and page number. A project executive can ask “are there any open submittals blocking the structural steel package?” and get a live answer that draws on both the submittal log and the project schedule simultaneously.
The company describes this as moving from a passive document repository to an active collaborator. In practice, it means the knowledge locked in a project’s documentation becomes accessible to the people who need it, when they need it, without a document controller or three hours of searching.
Buchner founded Trunk Tools with a specific frustration in mind. A trained construction engineer with a PhD, she had spent years watching project teams make expensive decisions based on incomplete information — not because the information didn’t exist, but because nobody could find it in time. “We built Trunk Tools to eliminate the guesswork,” she said at the time of the Series B announcement.
The Schedule Agent
The Series A announcement in 2024 centred on the company’s Schedule Agent — described as the first fully autonomous AI agent built specifically for construction scheduling. The agent monitors upcoming tasks, links scheduled activities to their supporting documentation, and alerts project managers, superintendents, and field engineers to open items, conflicts, and discrepancies before they become delays.
In practice, this means a superintendent starts the morning with a list of what is falling behind, what documents are needed to unblock it, and which subcontractors have outstanding deliverables. The administrative work of tracking that information — which might otherwise take an hour of cross-referencing spreadsheets and email threads — is compressed to a push notification.
Gilbane Building Company was among the early adopters at Series A. “Trunk Tools showed that it can help our teams increase efficiency and save significant time by preventing rework,” said Andy Roy, a Senior Superintendent at the firm.
The Intelligence Augmentation Argument
Buchner is deliberate about how she frames the technology. In public remarks, she has positioned Trunk Tools not as artificial intelligence in the replacement sense but as intelligence augmentation: reducing the tedious manual work so that builders can concentrate on construction.
That framing matters commercially as well as philosophically. Construction has a skills crisis — the United States alone is short roughly 500,000 workers — and the industry cannot afford tools that threaten to automate tradespeople out of roles. What it can adopt, and is adopting, are tools that make the people it has more effective.
The distinction also positions Trunk Tools against the broader category of AI hype. Where some platforms lead with benchmark claims and demo videos, Trunk Tools leads with documented time savings on real projects and references from working superintendents.
Where the $40 Million Goes
Insight Partners, which led the Series B, has a history of backing enterprise software companies at the growth stage — a pattern that fits Trunk Tools’ current position: product proven in the field, early revenue, ready to scale sales and engineering simultaneously.
The company plans to use the capital to expand its engineering and product teams, scale go-to-market, and deepen AI capabilities for complex construction scenarios and edge cases — the kinds of projects where documentation is messiest and the cost of information failure is highest.
The global construction market was valued at $11.4 trillion in 2024 and is projected to reach $16 trillion by 2030. Even a small improvement in information access across that market represents an enormous addressable opportunity. Trunk Tools is betting it can own the document intelligence layer before the incumbents decide the problem is worth building for themselves. That race is already underway: Procore’s AI Copilot and Autodesk’s Project Data Agent both target the same document-retrieval workflow from their respective platform positions.
