Insurtech Cowbell, Provider of Cyber Insurance for SMEs, Partners with Skyward Specialty Insurance Group

Cowbell, a provider of cyber insurance for small and medium-sized enterprises (SMEs), and Skyward Specialty Insurance Group Inc. (NASDAQ: SKWD) , a firm focused on the specialty property and casualty market, announced a partnership agreement that “expands Cowbell’s coverage and capacity of its Prime 250 Cyber Liability and Prime Tech, a recently introduced insurance program that safeguards businesses generating revenue of up to $500 million against cyber and technology errors and omissions (E&O) risks.”

The alliance “leverages Skyward Specialty’s expertise in bringing inventive insurance offerings to underserved markets that directly address growing risks unique to those businesses.”

Additionally, the partnership “provides Cowbell access to Skyward Specialty’s key industry partners to strengthen its capacity to deliver comprehensive coverage to meet evolving market needs.”

Andrew Robinson, Skyward Specialty CEO, said:

“Partnering with Cowbell is another bold step in our strategy to lead in our chosen markets. We have spent over a year getting to know Cowbell, their leadership and team, and have been impressed by the underwriting precision they achieve, and their unique approach to continuous cyber risk assessment. This partnership is a powerful combination of two great companies.”

Jack Kudale, Founder and CEO of Cowbell, said:

“We continuously monitored 95% of U.S. SMEs cyber risks for the last four years and have found that there’s a massive gap in cyber protection that is overlooked for this vastly underserved market. The insurability gap for these businesses is championed through this exciting new partnership with Skyward Specialty. This partnership leverages the expertise of the deeply experienced leaders and team members at Skyward Specialty, some of whom were part of helping to create the cyber insurance marketplace over 20 years ago.”

The partnership will “aid in expanding Cowbell’s omnichannel distribution network, which currently comprises over 23,000 appointed agents and 3,500 agencies across all retail, wholesale, and embedded channels.”

The collaboration “expands Cowbell’s reach to a broader range of businesses and provides technology companies with E&O coverage.”

Consequently, Cowbell’s growing portfolio will now “serve a significant portion of underserved small and medium-sized enterprises seeking financial security against cyberattacks.”

Cowbell’s appointed broker partners “will now have access to Primary and Excess Cyber coverage for accounts up to $500 million in revenue.”

As covered, Cowbell claims it is “a pioneer of Adaptive Cyber Insurance, a leader in providing small and medium-sized enterprises (SMEs) coverage adaptable to today’s and tomorrow’s threats and the advanced warning of cyber risk exposures.”

In its unique AI-based approach to risk selection and pricing, Cowbell’s continuous underwriting platform, “powered by Cowbell Factors, compresses the insurance process from submission to issue in less than 5 minutes.”

Cowbell is backed “by 20 prominent leading global (re)insurance partners and serves SMEs in 50 U.S. states and the District of Columbia.”

Founded in 2019, Cowbell is “based in the San Francisco Bay Area with employees across the U.S., Canada, India, and the U.K.”



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Disclosure Quest

Reg A - Form 1-A Filings Beta

Beta. Initial Form 1-A only. Target raise is the stated Amount to be Raised, totaled. Compared with the same dates one year earlier.

YTD: Jan 1, 2026 - Nov 5, 2026 vs Jan 1, 2025 - Nov 5, 2025

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Number of Filings134Prior 129 +3.9%
Target Raise, Total$3.45BPrior $3.59B -3.8%
This YTDYear priorChange
Filings 134 129 +3.9%
Target raise $3.45B $3.59B -3.8%

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