AI in Legacy Industries (Part 1): Customer Discovery, Nailing GTM, and Navigating Product Expansion
In Conversation: Matt Calvano (CEO and co-founder of Adaptive)
By Claire Biernacki, Susan Lyne & Cindy Fan, BBG Ventures
Legacy industries like manufacturing, agriculture and construction are the quiet giants of the U.S. economy, making up over half of GDP, but many still run on paper trails, phone calls, and spreadsheets. At BBG Ventures, we’re excited to back the next wave of companies building for foundational industries disrupting the “this is how we’ve always done it” mentality. We teamed up with Construct, Avid Ventures, and NVP to host a breakfast conversation with Matt Calvano, founder and CEO of Adaptive to dive into tactical strategies for disrupting the status quo in legacy industries.
Adaptive is an AI-powered financial management platform for construction. The product automates finance end-to-end — across billing, receipt capture, budgets, reporting, and more — all of which fully integrate with Quickbooks, Procore, and other systems that builders actually use. What started as a simple accounts payable tool is now a full-stack accounting system used by 600+ contractors.
We unpack how Matt and his team took a customer-led approach to identifying the problem, how they got distribution in a trust-based industry, and how automation done right can create an undeniable wedge into legacy workflows.
From Real Estate to Construction Bookkeeping
Though Matt started off his career in banking and real estate private equity, his first taste of legacy industries and entrepreneurship came from running a painting business in college. He began exploring founding more seriously during his time at Stanford’s Graduate School of Business.
Matt’s original plan wasn’t to tackle construction bookkeeping. Given his background in real estate, he initially raised a pre-seed to build software for real estate developers — building a data model for rezoning — and spending six months on the idea. But every developer he talked to pointed to the same problem — bookkeeping. This led them to a pivot to focus on serving builders.
Instead of building a product right away, Matt and his team needed to better understand the painpoints, and decided to do this first-hand — by operating as bookkeepers. For three months, they ran the books for a handful of builders in Austin, learning the hard way that “clean reporting” was less about analytics; reporting software like Quickbook and Procore already existed and they still didn’t know how their projects were performing. The real problem was messy, slow, and error-prone inputs — the many daily transactions comprising bills, expenses, and labor counts that had to be approved by multiple people before hitting the books.
This insight flipped their approach. Instead of starting with pretty outputs, they started by fixing the workflows that feed them. Their first product was automated accounts payable — which has since evolved into labor tracking, receivables, and approvals: a full-stack accounting system tied directly to jobsite operations. Today, Adaptive integrates with Procore, QuickBooks, and other core systems, supporting builders from input through reconciliation.
Takeaway: Stay nimble in customer discovery. A boots-on-the -ground approach and time in-person is the fastest path to understanding the real problems — watch what’s broken in their current process and start there.
GTM: Win the “Cool Kids” First
Matt knew Adaptive wasn’t going to spread through product-led growth and viral signups — construction is a trust-based industry that relies on recommendations from peers. Builders aren’t browsing Product Hunt — they’re on-site, racing against deadlines. But as Matt said, “They’re also not tech resistant. They just want software that fits into their workflow.” The initial go-to-market motion was primarily outbound and focused on SMBs — getting in front of them in person. “It’s like being the new kid at school. You go to the cool kids” (or the key construction players in this case) and try to win them over.
Once those early wins were in place, Adaptive was able to establish partnerships that included large CPA firms eager to expand beyond tax and audit into CFO services. For example, a deal with one of the largest accounting firms in the US brought access to thousands of new builders through a trusted referral loop.
As they honed in on PMF, the sales pitch evolved. These partnerships, growing brand recognition, and an increase in inbound enterprise interest gave the team confidence to go after larger enterprise customers.
While selling to SMBs was more about trust and reliability over ROI, enterprise buyers wanted ROI proof — for which Adaptive had already built with data from their SMB customers. With dozens of project managers, each with an admin entering data into Procore, enterprises were receptive to an AI product with obvious workflow automation gains. This was about improved invoice accuracy, faster close cycles, and measurable cost savings.
Takeaway: The sales motion changes as you move upmarket — from building trust to concrete ROI. Even though your customers may not be ROI focused in the earliest days, establish an understanding of how you’ll position ROI as you evolve.
Building With an Eye Towards the Big Vision
From the start, Matt knew they weren’t building a point solution — the accounts payable tool was just the wedge into a platform solution. Adaptive’s early goal and vision was to own the full accounting workflow for construction. There are certain elements of the product roadmap that customers may not be asking for yet — but are logical extensions. Tactically, they structure the engineering team to handle fixes with the current product while also having time for more strategic projects that align with the long-term vision.
Matt’s advice to founders: you don’t have to call yourself a platform, but you should know if you’re building one, even if your customers can’t see the whole roadmap yet. That intentionality informs everything from how you hire to how you prioritize features and position the product.
Takeaway: Continue to serve your customer more deeply through a deliberate product roadmap. Part of the roadmap will come from listening to your customers, but founders should also intentionally think through natural product extensions.
Leveling Up with AI; But Product Experience and GTM is the Real Moat
Adaptive’s core value proposition has always been about automation, but LLMs have taken the vision to the next level, enabling them to meet customers where they are by pulling data out of their email inbox.
When we asked how Matt positions AI in an industry famous for the “this is how we’ve always done it” mindset, we learned that AI is actually part of the pitch — there’s always a subset of builders curious about bringing AI into their workflows. For the skeptics, Matt frames Adaptive like an analyst: it preps everything a project manager or controller needs, and they review it. Multiple layers of approval remain. “It’s like hiring someone new,” Matt explained. “At first you check all their work. Eventually, you don’t need to.” AI has helped Adaptive automate more, experiment faster, and deepen workflow integration — but trust still builds over time.
On the technical side, the team built an in-house evaluation system to continuously test and improve LLM performance. In just two months, they dramatically boosted invoice-matching accuracy — another example of removing the low-value, manual work that keeps builders from making decisions quickly.
But Adaptive’s long-term moat isn’t about the underlying model. For tech-resistant customers, simply unlocking a repeatable sales motion is a huge advantage. The stickiness comes from how seamlessly the product fits into daily workflows, and the depth of its integration into core operations — Adaptive’s product is hard to rip out.
“We didn’t win because we had the best AI,” Matt said. “We won because we fit into the way they already work and made their lives easier.”
Takeaway: The moat isn’t just the tech, but also the user experience, speed, and how central your product becomes to real work.
Playbooks for a High-Performance Team
As the team grew, structure became just as important as speed. Matt realized the “figure it out” ethos that worked for an early team of generalists wouldn’t scale as he needed to hire specialists. The team needed playbooks that enabled individual team members’ strengths, not just hustle. Hiring people from industry (especially in areas where the team doesn’t already have expertise) can also be quite valuable and level up the team. For example, on the sales side, Adaptive’s first sales hire came from a well-known company in construction software, who brought industry know-how and relationships to the team. In closing candidates, they’ve also leveraged their top customers, who were advocates of the business to pitch the value proposition and potential of the company.
Takeaway: As you hire more specialists, implement structure to amplify their strengths. Use customers as your advocates in selling candidates coming from “hotter” sectors.
Raising a Series A
Adaptive was fortunate enough to get pre-empted for Series A from an investor who had been wanting to make a bet in construction finance for 10 years (talk about having a thesis!). Matt’s advice was to spend time with investors who already have a thesis in the space — so you don’t spend your time educating them. We also asked the Series A investors in the room about their advice, which focused on:
Timing the raise with a clear unlock for the business: Don’t raise with the story of “this is what I need to go do” but when you’re ready to scale. Show evidence that GTM is starting to work and adding more capital will unlock and supercharge growth. Have data to support that this is repeatable.
PMF: Wait to raise until you have real evidence of product-market-fit — these sectors are slow to adopt new technology, so it can take time.
Credibility and trust: In legacy industries, customer confidence and referenceability matter. You need customers that love your product for a successful raise.
Takeaway: Unlocking PMF in categories where trust is key is critical to raising a Series A. Investors want to invest when GTM is starting to work and adding more capital will unlock the next phase of growth.
What We’re Excited About at BBGV
At BBGV, we’re excited to back underrepresented founders leveraging AI in legacy and overlooked industries, helping their customers automate workflows end to end. If you’re building in this space — or you are an investor exploring the impact of AI on industry-specific innovation — we’d love to connect. Reach out: claire@bbgv.com and susan@bbgv.com.
About BBGV:
BBG Ventures is a pre-seed and seed fund investing in underestimated founders building solutions for our polycultural future. Our founders are tackling the biggest arenas of the economy that require reinvention: health and wellbeing, work and education, financial security, energy resiliency and overlooked consumers. We look for founders who want to move the world forward, and whose unique combination of lived and learned experiences give them a competitive advantage.