Cowbell launches AI-native underwriting system

The new Decision Intelligence System has cut quote times from days to minutes

Cowbell launches AI-native underwriting system

Cyber

By Josh Recamara

Cowbell, a provider of AI-native cyber and specialty insurance for small and medium-sized enterprises (SMEs), has launched OMNI, an AI-native Decision Intelligence System built to support underwriting, claims and product development across its specialty insurance business.

Built on the Cowbell Platform, OMNI combines decision intelligence, workflow automation, and governance. It draws on Cowbell's global risk pool of more than 55 million entities and is designed to help underwriters, claims advisors, and cybersecurity staff make faster, more consistent decisions across the insurance lifecycle.

Targeting a persistent underwriting bottleneck

The first application of OMNI targets a long-standing challenge in specialty insurance: underwriting high-volume, lower-premium excess and surplus (E&S) business for smaller organizations, where per-account premiums have historically been too thin to support traditional, labor-intensive underwriting.

Specialized AI agents work alongside human underwriters to analyze submissions, evaluate risk, and gather underwriting intelligence, generating coverage and pricing recommendations that underwriters retain final authority to approve.

Cowbell said eligible non-admitted quotes can now be delivered in minutes rather than the days or weeks typical of conventional specialty insurance workflows, and that new business has grown 53% since the platform's deployment - figures that are self-reported by Cowbell rather than independently verified, and worth reading with that in mind given their scale.

"Specialty lines are increasingly defined by bifurcation," said Jack Kudale, founder and CEO of Cowbell. "The market remains highly risk-segmented, requiring more granular underwriting as pricing pressure intensifies and loss costs, litigation, and volatility remain elevated. With OMNI, we are unifying intelligence, automation, governance, and performance measurement into an AI-native Decision Intelligence System purpose-built for specialty insurance."

Cowbell said the platform has also compressed product development timelines from roughly eight months to as little as six weeks, citing the recent launch of Prime One, a cyber product for the US middle market. Bellwether, its internal AI performance measurement tool, is meant to track adoption and outcomes to keep AI-assisted decisions auditable.

A persistent SME coverage gap

Cowbell's push to automate specialty underwriting arrives against a backdrop of chronic underinsurance among the SME segment it serves. Cyber insurance penetration among US small businesses sits at roughly 10% to 20%, compared with 60% to 70% among large corporations, according to Swiss Re. Munich Re estimated the addressable US small business insurance market at approximately $175 billion, with about 75% of small businesses underinsured.

Founded in 2019 and based in Pleasanton, California, Cowbell has raised more than $200 million to date, including a $60 million investment from Zurich Insurance Group in 2024. The company has built its business on continuous, data-driven underwriting rather than static questionnaires, reassessing risk on an ongoing basis rather than only at renewal.

"Insurance doesn't need another chatbot," said Rajeev Gupta, co-founder and chief product officer at Cowbell. "OMNI goes further by orchestrating decisions across the entire specialty insurance lifecycle." Gupta added that the goal is for each underwriting decision and claim to inform the next as the system continues to learn.

A crowded field of AI-native cyber underwriters

Cowbell competes in a crowded field of AI-forward cyber insurers that includes Coalition, At-Bay, Resilience, and Corvus, acquired by Travelers in 2024. Coalition bundles continuous security monitoring with coverage, while At-Bay emphasizes underwriting that addresses AI vendor and third-party model risk.

Cowbell's differentiation rests on its focus on the smaller end of the SME market and on continuous underwriting that ties pricing to a policyholder's observed risk profile throughout the year rather than only at renewal.

Regulatory scrutiny of AI underwriting is rising

Cowbell's expanded reliance on AI agents in underwriting comes as US regulators sharpen oversight of algorithmic decision-making.

More than 24 states and the District of Columbia had adopted the NAIC's Model Bulletin on the Use of Artificial Intelligence Systems by Insurers by early 2026, requiring carriers to maintain a written AI governance program covering model validation, bias testing, and third-party AI oversight.

The NAIC has also begun piloting an AI Systems Evaluation Tool with a group of insurers, giving state examiners a standardized framework for reviewing AI governance during market conduct exams.

For carriers embedding AI deeper into underwriting, that apparatus makes documentation a live compliance issue rather than a future one.

A test case for AI-native underwriting at scale

Cowbell's rollout adds to a broader push across specialty and E&S carriers to apply AI directly to underwriting rather than confining it to back-office automation.

Its emphasis on human sign-off, paired with a dedicated tracking tool in Bellwether, reflects a wider industry effort to build governance into AI-assisted underwriting as regulators formalize how such systems will be examined.

Whether OMNI's reported gains hold up as the platform scales across claims and cyber resilience, alongside Cowbell's expansion into Europe and Asia-Pacific, will test how much AI can compress underwriting cycles in a segment long constrained by thin per-account economics and now facing closer regulatory attention.

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