Ola Kolade is challenging how the insurance industry thinks about automation

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The Underflow CEO and former investment banker says the industry has spent two decades automating the wrong thing. His AI-powered alternative is turning heads.

The commercial insurance industry has no shortage of technology vendors promising to modernize underwriting. Over the past decade, insurtech startups have raised billions of dollars on the premise that software can make the process faster, cheaper, and more accurate. And yet, by most measures, the core submission workflow has barely changed.

Ola Kolade has a theory about why:

“The industry kept trying to automate the container instead of automating the work,” Kolade said. “You can digitize a filing cabinet. You can build a prettier inbox. But if the underwriter still has to open every attachment, read every page, type every data point into a system, and draft every follow-up email by hand, you have not actually automated anything. You have just given them a nicer desk to do the same manual work.”

It is a pointed critique, and one that has been gaining traction. Kolade, the CEO and co-founder of Underflow Inc., a San Francisco-based startup that has raised $3 million in seed funding, is building what he calls an autonomous underwriting assistant. The product, called Aurora, does not attempt to improve the existing workflow. It attempts to eliminate the manual portions of it entirely.

The numbers behind the problem

The scale of the inefficiency Kolade describes is well documented. Capgemini’s 2024 World Property and Casualty Insurance Report found that 41 to 43 percent of commercial underwriters’ time is spent on administrative activities including data entry and record keeping. Only about one-third of their time goes to core underwriting functions like risk assessment and premium calculation.

Accenture’s research paints an even starker picture, finding that the average commercial underwriter spends approximately 70 percent of their time on non-underwriting activities. The firm estimated the cumulative cost of this inefficiency at $85 billion to $160 billion over five years across the industry.

These are not obscure statistics in the insurance world. Executives at carriers, managing general agents, and wholesalers cite them regularly. The question that has frustrated the industry for years is what to do about it.

An outsider’s diagnosis

Kolade did not come up through the insurance ranks. A Canadian citizen who studied economics at McGill University, he began his career in investment banking at National Bank Financial in Toronto, where he worked on more than ten transactions across the technology sector. He later moved to San Francisco to lead strategic finance at Faire, one of North America’s largest wholesale marketplaces, where he led the upmarket business unit responsible for the platform’s largest retail customers.

Before that, at Power, Kolade negotiated $10 million in debt financing, built integrated three-statement financial models and KPI dashboards underpinning major capital raises, and led a strategic advisory board coordinating quarterly meetings with executives across the organization.

His introduction to commercial insurance came through Faire, where he observed the risk management processes of the thousands of independent businesses on the platform. He began studying the commercial insurance distribution chain, and what he found struck him as a fundamental mismatch between the sophistication of the people in the industry and the primitiveness of their tools.

“I came from an environment where we used machine learning to match retailers with inventory in real time,” Kolade said. “And then I looked at how an insurance submission moves from a broker to a carrier, and it was email threads, PDF attachments, and manual re-keying into legacy systems. These are brilliant professionals working with tools from 2002.”

The comprehension gap

Kolade published his analysis of the problem in December 2025 in Rough Notes, one of the oldest insurance trade publications in the United States, founded in 1878. The article, which examined why traditional software has failed to transform underwriting workflows, argued that prior solutions addressed the wrong layer of the problem.

The core issue, Kolade wrote, is not that documents are hard to store or organize. It is that they are hard to understand. A typical commercial insurance submission includes ACORD applications, loss runs from prior carriers, schedules of values, and supplemental forms. Each document contains data that must be interpreted in the context of a specific line of business, cross-referenced against carrier requirements, and evaluated for completeness and consistency.

“Optical character recognition can read the text on a page,” Kolade said. “It cannot tell you that the loss run is two years short of what the carrier requires, or that the construction type listed on one form contradicts the information on another. That is the gap. Not reading. Comprehension.”

How Aurora approaches the problem

Aurora, the product Kolade has built through Underflow, connects directly to a firm’s existing email environment. When a submission arrives, Aurora reads the email and every attachment, extracts all relevant data, and structures it into a unified record. It then performs a granular gap analysis, identifying not just that a submission is incomplete but specifying exactly what is missing and why.

The system then drafts and sends follow-up communications to the broker, either under its own identity or through the firm’s email accounts. If a response does not arrive within a defined period, it follows up again. When the file is complete, Aurora packages it and routes it to the assigned underwriter.

Critically, Aurora also performs functions that go beyond intake processing. It writes preliminary risk assessments, flags inconsistencies across documents, identifies potential coverage opportunities, and enriches submissions with research from public data sources including property records, business registries, and corporate profiles.

“We are not building a faster version of the existing process,” Kolade said. “We are building a system that delivers a better outcome. The underwriter should receive a file that is not just complete but contextualized, with analysis already done and external data already integrated. That is the standard Aurora is built to meet.”

The retirement cliff

Kolade’s thesis is sharpened by a demographic reality the industry has been watching for years. Roughly one quarter of the commercial insurance workforce is aged 55 or older, and the institutional knowledge they carry, including carrier appetite familiarity, risk pattern recognition, and relationship context built over decades, is not something that can be transferred through a training manual.

“The industry is losing 20 and 30 years of experience every time someone retires,” Kolade said. “You cannot hire your way out of that. The math does not work. What you can do is capture the repeatable parts of that expertise in a system that scales, so your remaining professionals can focus on the judgment calls that actually require human experience.”

Skepticism and the path forward

The insurance industry’s relationship with technology has historically been cautious. Adoption cycles are long, switching costs are high, and trust in new systems is hard-won. Kolade says he anticipated this.

“We built Aurora to work inside email because that is where insurance happens,” he said. “We do not ask anyone to change how they send submissions. We do not require a new portal or a new login. The broker sends the email the way they always have. The difference is what happens when it arrives.”

Whether Underflow can overcome the industry’s institutional inertia is the central question facing the company. But Kolade’s framing of the problem, distinguishing between document management and document comprehension, has resonated with practitioners who have watched previous technology waves fail to deliver on their promises.

As Kolade wrote in Rough Notes: “Speed has always determined who gets the business. Now it will determine who stays in business.” The industry, it seems, is listening.