RenewTrack

RenewTrack was founded in 2014 to solve a problem Matthew Cagney would experience firsthand at Afterpay: the chaos of contract renewals. When a key software renewal expired without notification, his entire platform was shut down, and customers woke him up on a Sunday morning unable to transact. That frustration led him to invest his own money in RenewTrack's vision. But when he joined as CEO in 2020, the company had spent six years building something that barely worked—only 2 customers, high churn, and a product so fragmented it felt like managing six different companies.

The original founders had a brilliant concept: repurpose collection software to proactively notify customers about upcoming renewals and offer e-commerce checkout. It was genius, and they managed to land two early customers and secure angel funding. But the product couldn't scale. Each customer required custom data ingestion, and vendors' data was messy, fragmented, and often obfuscated through sales channels. By the time Matthew arrived, the engineering team was spending 95% of their time putting out fires instead of building new features. The codebase had grown to six separate "products" with 25,000 lines of code each—an unmanageable mess.

Matthew's first move was brutal triage. He shut down third-party sales channels, overseas call centers, and marketing efforts—anything burning cash without clear product-market fit. He made a principle: "If our own team can't sell, there's no point engaging a channel." So he went back to basics, spending 60% of his time on cold outreach via LinkedIn and email, personally calling executives at tech companies. For the first deals, he relied on his co-salesman Randy's existing relationships. The breakthrough came when they won Lenovo, a massive customer with enormous data volumes that immediately stressed their infrastructure. Winning Lenovo was shocking—it wasn't a gradual climb, it was a leap.

Matthew's genius move was decoupling product work from customer success. While the engineering team (led by newly hired CTO Andrew) spent a year reengineering the data ingestion engine and consolidating to a single codebase, Matthew over-invested in customer service. He hired senior customer success talent and wrapped around existing customers multiple times per week, manually doing the work his product couldn't yet do: creating actionable intelligence reports, helping vendors optimize renewal campaigns by geography and tax jurisdiction, enabling channel partners to adopt the platform. This "service bridge" kept customers happy while the product team fixed the foundation.

He also made a critical pricing pivot. Originally, he'd copied Afterpay's model: charge a percentage of successful renewals. But renewals take 3-6 months to close, creating a cash flow nightmare. A new investor, Title Ventures, pushed him to subscription: split the revenue between a monthly subscription fee and a percentage success component. This shift to advance quarterly billing dramatically improved cash flow and company stability.

For go-to-market, Matthew narrowed focus ruthlessly. Instead of trying to be global from day one, he picked specific geographies (starting with EMEA, then France/Turkey for VMware) and specific products to prove value before expanding. He quantified where each vendor had the worst renewal rates and where he could move the needle fastest.

As of the podcast recording, RenewTrack is at $6 million ARR with 16-18 customers. The team is 34 people globally. Customers include VMware, Lenovo, HP, Cisco, and Precisely. The product is now a single, scalable codebase with an AI-powered data ingestion engine. Matthew credits his survival to three things: recruiting "one-man-army" developers who were worth 4-6 normal engineers, trusting his intuition that the problem was real and solvable, and never giving up even when the first two years were "the hardest and most stressful of my career." His advice: if a customer says no, dig deeper. "The selling only starts when the customer says no."