The useful part of Jordan Katz’s story begins with a bad product. In college, he spent thousands of hours building a software platform that sprawled to roughly 500 features. In his later telling, each was about five percent finished. The project had ambition in bulk and judgment in short supply. Katz called it a “huge dumpster fire.” It did, however, leave behind one excellent result: a young builder who knew how much he did not know.
Katz went looking for instruction. He encountered Cracking the PM Interview, the book by Gayle Laakmann McDowell and then-Asana product leader Jackie Bavaro. About 20 pages in, he made an unusually specific career decision: he wanted to work for Jackie. After graduating from the University of Michigan’s Ross School of Business, with a computer science minor, he joined Asana as a product manager.
The choice says something about Katz’s instincts. He did not respond to a failed build by promising himself a better build. He sought a place where good product work was already happening, then apprenticed himself to the craft. At Asana he worked across teams through the company’s run toward its public listing. He later became the first product hire at Pathlight. By the time he was ready to found another company, he had replaced the college habit of adding features with the professional habit of asking which problem deserved one.
A co-founder, delayed
Near the end of college, another student named Michael Mattheakis asked Katz to lunch. Mattheakis was curious about product management; Katz was headed to Asana. The conversation landed with the force that founders sometimes reserve for retrospective origin myths. Katz remembers thinking that this might be somebody he would start a company with. Mattheakis, Katz has joked, did not appear to suffer the same immediate revelation.
They became close friends anyway. Mattheakis joined Brex when it had about ten employees and watched it grow to more than 900. Katz learned product at Asana and Pathlight. Eventually they began working nights and weekends on startup ideas. The partnership paired Katz’s product training with Mattheakis’s engineering experience, plus the trust accumulated before either needed the other to sign a cap table.
“We just felt Silicon Valley didn’t need more software for itself.”Jordan Katz, on abandoning “SaaS for SaaS”
Their first instinct was familiar: build revenue software for SaaS companies like the ones they knew. Customer conversations spoiled the thesis. Existing products were imperfect, but the founders could not see a path to something vastly better. Software people had already been extremely industrious about building software for software people. Katz and Mattheakis wanted to make something that did not already exist.
The extra accounting
They started learning about insurance. It presented a different landscape: paper, PDFs, spreadsheets, aging software and people copying information between them. The pair were especially drawn to accounting. A premium payment can pass among carriers, brokers and other intermediaries, each maintaining its own records and each capable of repeating a reconciliation that another party has already performed. Policy data may disagree with a commission statement. An exception becomes a row in another spreadsheet. The oddity was not that insurance had accounting. It was that insurance appeared to have an extra species of it.
The standard industry refrain, the founders recall, was that nobody had solved it yet. To a reasonable person, this can sound like a warning. To two outsiders furnished with what Katz called “naive, wide-eyed optimism,” it sounded like a question: what if they could?
Optimism did not make the early calls friendlier. One executive began a conversation by explaining that he was taking it only as a favor. His company did not need their services, he said; the problem was handled. Katz and Mattheakis put the quote on their office wall. At first it had been a blow. With more interviews, it became evidence of something subtler: an executive may have authority over a workflow without being close enough to feel every papercut inside it.
So the founders kept calling. They asked about edge cases, watched work being done, and tried to understand why each awkward step existed. Their lack of sales polish may have helped. The questions sounded less like a pitch and more like the beginnings of a product. The company that said it did not need Comulate eventually became one of its largest customers.
Proximity beats posture
One early customer stayed close to the founders as they learned. When she retired after 50 years at her company, she sent Katz a note. Working with Comulate, she wrote, was the first time somebody bringing in a product had seemed to understand the team. For Katz, the message captured the difference between approaching a market with a product manager’s curiosity and arriving with a salesperson’s promises.
This became Comulate’s method. The company built software to ingest carrier statements in varied formats, match them against policy and payment records, surface exceptions, automate reconciliation and improve revenue reporting. As customers reclaimed time, they asked the company to handle adjacent work. A narrow wedge widened through observed need rather than a slide labeled “platform.”
By early 2025, Comulate said it had automated the reconciliation of billions of dollars and reached eight-figure annual recurring revenue in less than three years. Its customers included IMA Financial, The Baldwin Group and Hilb Group. Revenue tripled during 2024. Instead of announcing a Series A, the company moved from earlier seed backing to a $20 million Series B led by BOND and Workday Ventures, with existing investors including Spark Capital.
Money can make any founding story appear preordained, which this one plainly was not. Comulate emerged from discarded ideas, awkward introductions and two founders learning a vocabulary that their eventual customers had used for decades. Even its most quotable rejection did not reveal itself as useful until they had done enough work to interpret it.
The constraint beneath the workflow
Katz’s more interesting argument about AI is not that it can accelerate an existing series of clicks. He asks what fundamental constraint caused that series to exist. A workflow designed around the limits of paper, static PDFs or brittle software may not deserve a faster version. It may deserve a new shape.
That distinction is particularly relevant in insurance, where a process can be both sleepy and critical. Comulate’s appeal is not that it makes reconciliation sound thrilling. The work remains consequential because the money must be right. Its promise is that people should spend less of their intelligence performing the same match repeatedly and more of it resolving the exception that genuinely needs judgment.
That last milestone mattered to Katz for reasons larger than attendance. Three years earlier, he and Mattheakis had worked from a small San Francisco apartment with no product and no insurance track record. At BALANCE, accounting teams and CFOs who had collaborated remotely met in person, swapped strategies and compared uses of the software. Katz called the “human energy” of those early believers a compass. Software companies speak often about community; here, the community began as the people patient enough to explain why a payment did not match.
A more contested chapter
Comulate’s rise has also brought conflict. Since late 2025, it has been locked in litigation with established insurance software provider Applied Systems. Applied has accused Comulate of misrepresentation and misuse of access to its Epic platform. Comulate has denied using Applied code or intellectual property in its products and has pursued antitrust claims concerning Applied’s control over customer integration access. Court proceedings continued in 2026. The dispute is unresolved, and the competing accounts belong in a courtroom, not a founder fable.
It nevertheless marks a change in Comulate’s circumstances. Outsiders may begin with the freedom of having little to lose. Once customers, revenue and rivals accumulate, every product decision acquires legal and competitive weight. Katz is no longer merely asking an unfamiliar industry to take two young founders seriously. He is leading a company whose place in that industry is consequential enough to be contested.
The durable lesson in his story is less dramatic than disruption and more transferable. Choose a field where real work is being ignored. Admit what you do not know. Find the person closest to the mess. Ask why the awkward step exists, then ask again. A spreadsheet is not glamorous, but glamour has never reconciled a commission statement. Attention sometimes does.