In construction, the numbers that determine whether a job is profitable rarely live where the accounting happens: a project’s true cost to complete, the cost code a change order belongs to, and what a subcontractor is owed this month typically sit in a superintendent’s head, a daily log, or a text thread rather than in the books, and closing that gap has always meant someone in the office calling, texting, and emailing the field, then typing the answers in by hand. Past attempts to fix this largely asked the field to change its behavior, adding another login for a super or project manager to check between running a job site and coordinating subcontractors, which is part of why so much of that coordination still happens by phone call instead of software. Adaptive takes the opposite approach, sending AI agents out to reach supers and project managers by voice, text, and email on their own schedule, then routing what comes back into job costing, accounts payable, billing, work-in-progress, and compliance without anyone at a desk chasing it down or re-entering it. The agents operate inside a contractor’s existing accounting system rather than replacing it, and every action still passes through a human before it posts to the ledger, a design that has let Adaptive sell not only to general contractors, specialty trades, and developers but to the more than 40 accounting firms that manage books on their behalf. More than 750 construction companies, ranging from $5M to $1B in annual revenue, now run their books on Adaptive across more than 10 accounting systems, from QuickBooks to Sage and Acumatica. As that field-to-ledger record accumulates project by project, the company is positioning it as something contractors can eventually draw on to flag which kinds of jobs tend to run into trouble before they bid the next one, not just to close the books faster.
AlleyWatch sat down with Adaptive Cofounder and CEO Matt Calvano to learn more about the business, its plans for the future, recent funding round, and much, much more…
Who were your investors and how much did you raise?
We raised $30M in Series B funding, led by Tidemark, with participation from our existing investors: Emergence Capital, Andreessen Horowitz, Pathlight, Definition, and 3KVC. That brings our total raised to $57M.
Tell us about the product or service that Adaptive offers.
Adaptive is an AI-native accounting platform built for construction. Our agents connect what’s happening in the field with the financial side, so job costing, AP, billings, WIP, forecasting, change orders, and compliance stay current instead of catching up at month end. We’re not replacing anyone’s ERP, we sit on top of it and feed clean, reviewed numbers back in.
What inspired the start of Adaptive?
Adaptive started as a completely different product, a zoning tool for real estate developers. While calling GCs to get rough cost estimates for that, I started asking about the biggest problems in their businesses, and kept hearing the same things: “I never know where profit is going to shake out until the end.” “I double paid my subs.” “I forgot to bill for a change order on a project that’s already closed.” My co-founders and I pivoted, but instead of building software right away, we rented an Airbnb and ran an actual bookkeeping firm for local construction companies for a couple of months to learn the problem from the inside. What we found was that the software that existed was painfully manual, and if a system is a pain to use, the field just won’t use it. That’s what led us to build something that does the accounting work itself.
How is Adaptive different?
We don’t ask field teams to learn new software. Our AI project accountant reaches supers and PMs by voice, text, or email, whatever they’ll actually respond to, instead of waiting for someone to log into an app. And nothing posts to the general ledger without a human reviewing it first. The AI does the typing but our customers’ teams still make the final calls.
What market does Adaptive target and how big is it?
We work with GCs, specialty trades, developers, and the accounting firms behind them, typically $5M to $1B in revenue. More than 750 builders run on Adaptive today. Construction is a $2T in market in the US and $13T globally.
What’s your business model?
Our model is flexible and built around each business’s specific needs. Each customer’s agents get configured around their own workflows and most go live in 30 days. Pricing gets figured out through a conversation rather than a price list, since it depends on each use case, and the commitment is month-to-month.
How are you preparing for a potential economic slowdown?
Adaptive helps contractors reduce manual work and take on more work without adding headcount, which matters even more when budgets tighten. And because our pricing is month-to-month rather than a long-term contract, customers get to see the benefit for themselves before committing to anything longer.
What was the funding process like?
I’d been following Tidemark’s writing since our seed round, so by the time we sat down together, the relationship had already been building for a while. That made a real difference. We were talking to investors who already understood the space and how we thought about it, rather than starting from scratch.
What are the biggest challenges that you faced while raising capital?
None of us came from construction, our backgrounds are in finance and tech. But before diving in to build a product, we ran an actual bookkeeping firm for construction companies to learn the ins and outs. That direct experience did more to build credibility than anything we could have said.
What factors about your business led your investors to write the check?
Our investors have pointed to how we’re not just helping teams do the work faster, we’re increasingly doing it for them, bridging the back office and the field so job-level costs don’t require someone manually coordinating between the two. They’ve also talked about how our customers describe Adaptive, several call it one of the most important tools in their stack, which is rare to see in construction software. Beyond the product, it comes down to believing in what we’re building and the team behind it.
What are the milestones you plan to achieve in the next six months?
Ship several additional ERP integrations to unlock more of the market. Deploy additional agents across adjacent parts of the accounting workflow.
What advice can you offer companies in New York that do not have a fresh injection of capital in the bank?
Keep going!
Where do you see the company going now over the near term?
This round goes straight into two things: building out what our agents can do across job costing, AP, billing, WIP, and compliance, and growing our teams in Boston and New York to support that.
What’s your favorite fall destination in and around the city?
The West Village and Hudson Valley.
