An Insurance Tech Startup Skipped Series A, Tripled Revenue And Landed Workday As An Investor

Insurance firms generate billions of dollars in revenue each year, but much of their back-office infrastructure is supported by obsolete systems, spreadsheets, and manual operations. Billing and revenue management—critical activities for brokerages and carriers—are frequently left to obsolete corporate software that was never designed for the industry’s specific difficulties.

Comulate is a startup that identified an underappreciated but critical problem and went all in. Bond and Workday Ventures recently led a $20 million Series B fundraising round for the startup, which develops technologies to streamline revenue operations for insurers. This recent rise follows an incredible year of growth—Comulate believes it will triple its revenue in 2024, skipping a Series A totally due to strong demand from huge insurance companies. While the company isn’t disclosing exact figures, it says its revenue is already in the tens of millions.

A SaaS Startup That Almost Didn’t Touch Insurance

Comulate’s story isn’t the typical Silicon Valley playbook. CEO Jordan Katz and CTO Michael Mattheakis didn’t set out to transform the insurance back office. In fact, their original idea was to build software for other SaaS businesses, what Katz describes as “SaaS for SaaS.”

The problem? That market was already saturated. “There’s a lot of software out there that does very similar things, built by other software professionals who know how to build good software for problems they’ve experienced,” Katz said. The realization hit: Silicon Valley didn’t need more software for itself.

So they looked elsewhere. Insurance wasn’t an obvious choice, and they admitted they knew little about it at first. But once they started digging in, they saw an industry that was financial-services-adjacent yet largely ignored by tech innovation.

A ‘Sleepy but Critical’ Problem

Billing and revenue management in insurance isn’t just outdated—it’s an operational headache. Agencies deal with millions of transactions, often scattered across multiple agency management systems (AMS), with data that doesn’t always match. Reconciling deposits, commission statements, and bonuses often requires manual intervention, leading to inefficiencies and financial discrepancies.

“It’s a sleepy, but critical area,” said Jay Simons, general partner at Bond and former president of Atlassian. And in enterprise software, “sleepy but critical” is often where the biggest opportunities lie.

Comulate saw an opening: automate what had long been accepted as a painful, slow, and error-prone process. And the results have been significant. The company says its technology has saved customers 260,000 hours of manual work by automating reconciliation processes that once required entire finance teams.

Why Workday Bought In

One of the more notable aspects of this funding round is Workday’s involvement. As one of the largest enterprise software providers for finance and HR, Workday typically operates at a much broader level. But Comulate’s narrow focus on insurance billing and revenue operations made it an attractive investment.

The company’s ability to integrate with agency management systems and automate reconciliations is particularly relevant for large firms managing billions in revenue. Today, Comulate’s customers include the Baldwin Group, IMA Financial, Risk Strategies, and The Hilb Group—firms that handle massive transaction volumes and previously relied on fragmented, manual workflows.

For brokerages, revenue accounting isn’t just about tracking income—it impacts the entire business. The manual nature of the process creates operational inefficiencies that ripple across finance teams, carrier relationships, and even compensation structures.

One major issue is how compensation details from carriers get lost in the chaos. Many firms deal with multiple commission structures—per-employee-per-month models, percent-of-premium, and bonus programs. But finance teams often struggle to track these payments accurately. Some firms don’t even record certain revenue streams because the manual effort is too high.

Bonuses and overrides typically accounting for 10-15% of benefits revenue are another pain point. Many brokerage leaders say they lack clear visibility into what they’re earning, why they’re earning it, and how they can optimize these earnings. It’s a major gap that can directly impact a firm’s financial performance.

One of the biggest obstacles to modernizing insurance back-office functions isn’t just technical—it’s cultural. Many finance and accounting teams have spent decades relying on manual workflows, and shifting to an automated system requires breaking deeply ingrained habits.

However, according to Comulate, the transition is faster than many expect. “A top-30 brokerage CFO recently told me they were stunned that within a month of signing, a majority of their revenue reconciliation was already being automated,” Katz said. “They said it was the first time the decision and demo process was more work than the implementation.”

Comulate’s approach relies on what it calls “light AI” or “controlled AI”—machine learning models designed to ensure revenue integrity without unpredictable outputs. Unlike large language models (LLMs), which can introduce errors and inconsistencies, Comulate’s system focuses on precision. It digitizes financial documents, automatically matches transactions, and integrates directly into existing agency management systems.

This results in a reconciliation accuracy rate of over 90%—a figure that has led some accounting teams to call the system “magic.”

Enterprise-Grade Control

The insurance industry is inherently risk-averse, and that extends to its technology decisions. While AI is a buzzword across enterprise software, financial processes require a level of accuracy that traditional AI models struggle to guarantee.

Katz and Mattheakis understand this. “LLMs shouldn’t be used for most financial processes,” Katz said. “The system must use the data provided and produce consistent output given the same input, without hallucinations or generating new content.”

This focus on accuracy is one reason why some large brokerages are turning to Comulate not just for efficiency, but for risk reduction. Firms that previously relied on offshore teams for revenue reconciliation now see enterprise-grade software as a more secure and controlled alternative.

Comulate’s rapid growth has already exceeded the founders’ early expectations. Just a few years ago, they knew nothing about insurance accounting. Now, their platform processes billions in transactions and has reshaped how some of the industry’s largest players manage their revenue.