Riffle Founder Story: From Sticky Notes to Smarter Subs

When Adi Klinghofer and David Waxman started their subcontracting business, they didn’t set out to build software. They just needed a better way to keep up.

At first, it was just the two of them: estimating, quoting, and managing every project from their desks. Things ran smoothly enough until the business began to grow. More bids came in. More project managers joined the team. More moving parts had to be tracked.

“The system we had was Post-its,” Adi says, laughing. “They were everywhere… on my monitor, my desk, the walls. Notes about which GCs sent ITBs, which bids we’d sent out, and who needed follow-ups. It worked when there were two of us, but as soon as we had a team, we outgrew it overnight.”

Inbox chaos quickly became business chaos. Important bids got buried in threads. Team members double-quoted projects or missed deadlines. The old way of managing work, through Outlook, spreadsheets, and sticky notes, couldn’t scale with the pace of growth.

“We hit that point every sub hits,” David recalls. “We were growing, but we couldn’t see where we were winning or losing. We didn’t just need organization, we needed visibility.”

Building the Tool They Needed

So, they built one.

They started simple: a shared system that could pull in bid invites automatically, track who was handling what, and store everything in one central view. What began as an internal fix, a homegrown tool to make life easier, quickly became indispensable.

“It changed how we worked,” Adi says. “We weren’t wasting hours hunting through email or chasing updates. We could finally see our pipeline in one place.”

That clarity made training new project managers easier, too. “When we brought on new PMs, our internal tool that we built became our playbook,” David explains. “They could see what bids were open, how we structured them, and how to follow up. It wasn’t just about keeping track, it was about teaching consistency.”

Over time, the tool evolved into a connected workflow system, powered by automation and enhanced with AI, a single platform that brings estimating, collaboration, and tracking into one intelligent process. It didn’t just manage emails, it helped manage the business.

From Internal Fix to Industry Solution

At first, the platform was a private advantage, an internal tool that helped their company scale without adding more layers of management. But as they talked with other subcontractors, they realized everyone faced the same problem.

“Every sub we talked to was dealing with the same thing,” Adi says. “Too many ITBs, too many spreadsheets, and no good system to manage it all. They were spending hours on work that didn’t make them money.”

That’s when they decided to take it further and hand off the solution to a team who could help turn a contractor’s solution into a scalable SaaS product built on modern, AI-driven infrastructure.

The Next Chapter: From Concept to Company

To take the internal tool and build a modern platform, Adi and David brought on a team of SaaS product and technology leaders — Dan Olson (CEO), Jen Gadus (Chief Product Officer), and Joe Banks (Chief Technology Officer) — to create RiffleCM as a modern platform built for augmentation, automation, and insight.

“Adi and David built something every sub can relate to: a real, working system that solves a real problem,” says Dan Olson. “Our job was to take that practical foundation and layer in the intelligence and automation that today’s technology makes possible.”

Under Dan’s leadership, the Riffle team has focused on scaling what made the prototype powerful: simplicity, transparency, and automation that works behind the scenes. Jen Gadus, who brings deep experience in UX and workflow design, led the effort to ensure the product feels intuitive and adaptive, learning from how real teams use it.

“We wanted to keep that ‘built by subs’ DNA,” Jen explains. “But we also wanted Riffle to think like a great PM: anticipating what needs attention and surfacing insights automatically.”

Joe Banks, the company’s CTO, built Riffle on a modern, AI-enabled architecture designed for scalability and smart automation. “The real opportunity,” Joe says, “is to automate the repetitive stuff, inbox triage, version tracking, follow-ups, and then use AI to surface what matters most. Riffle doesn’t replace subs, it augments their decision-making.”

Built by Subs, Powered by Modern Tech

That blend of real-world trade experience and next-generation technology is what makes Riffle unique. The platform is grounded in actual subcontractor pain points but powered by advanced automation, data intelligence, and scalable design.

“Most construction tech starts with software people trying to learn the trades,” Dan says. “Riffle started with tradespeople and evolved into modern, AI-driven software built for how subs actually work.”

At launch, Riffle helps subcontractors manage their entire bidding process in one place: centralizing ITBs, estimates, and communications so nothing slips through the cracks. But the long-term vision goes further: project management, inventory, connecting to accounting systems, tracking profitability automatically, and delivering AI-driven insights on what drives margin and where to focus.

“It’s not just about getting organized,” David says. “It’s about knowing which jobs make you money, and letting the system help your team see that faster.”

The Future: Profitability, Visibility, and Augmentation

Today, Riffle’s focus remains on helping subcontractors streamline their bidding and estimating processes, the part of the business where opportunity begins. But the roadmap is clear: connect that front-end workflow to project profitability, giving subs a true picture of performance from bid to bank, powered by AI augmentation that transforms raw data into actionable insight.

“Once you can see your pipeline, the next step is knowing which projects are worth your time,” Adi explains. “That’s where the future of Riffle is headed: visibility, predictability, and smarter decisions powered by technology.”

For a trade that’s always been hands-on and relationship-driven, Riffle offers something new: a digital workflow that doesn’t replace experience, it amplifies it.

“Subs are the backbone of every project,” Adi says. “We just want to give them tools that work as hard and think as fast as they do.”