Cowbell Raises $25M in Round Led by Prosperity7 Ventures

The company has enjoyed rapid growth during 2023, increasing its new customer base 49 percent year over year.

(Image source: Cowbell homepage.)

Cowbell (Pleasanton, Calif.), a provider of cyber insurance for small- and medium-sized enterprises (SMEs), has announced significant momentum and new financing following its top-grossing quarter and amid continued corporate growth. Cowbell’s new financing of $25 million builds on its $148 million raised to-date.

Cowbell announced a new investment led by Prosperity7 Ventures (Dhahran, Saudi Arabia), with participation from new investors. The company reports that it has continued to grow its new customer base in 2023 by 49 percent year-over-year. Cowbell says its profitable growth path is also tracking positively, with a 43 percent ultimate loss ratio for 2022.

Chris Zhong, Investment Principal, Prosperity7 Ventures.

According to a recent study by the vendor, 72 percent of SMEs without cyber insurance say that a major cyberattack could destroy their business. Cowbell characterizes its success to date as closing the insurability gap for this critically important market, achieving 2.5x premium growth in 2022 to insure SMEs against evolving cyber threats.

Cowbell reports that it has widened its geographic footprint, recently launching operations in the U.K. market with Prime One for British SMEs. Cowbell says its vertically integrated technology platform, AI-based approach, and continuously monitored risk pool—now comprising 38 Million American and British businesses—remain key differentiators.

“The need for SMEs to augment their cybersecurity with a robust cyber insurance policy has never been greater, as more and more threat actors are targeting this market,” a Cowbell statement says. Since its inception, Cowbell 365, Cowbell’s dedicated risk engineering and claims management service has prevented extortion payments over 74 percent of the time and when a ransom must be paid, it’s reduced to an average of 26 percent of the initial demand, the company reports.

“Economic costs of cybercrime will reach $24T by 2027, accelerating cyber insurance adoption and growth even further,” comments Chris Zhong, Investment Principal, Prosperity7 Ventures. “We are investing in Cowbell’s strengths—its people, culture and unit economics. Prosperity7 is excited to partner with Cowbell on their path to profitable growth and near-term operating profitability as the company further cements its leadership in global SME markets.”

Strong Momentum

Jack Kudale, Founder and CEO, Cowbell Cyber.

“Momentum and policyholder growth is strong, with record renewal retention,” comments Jack Kudale, Founder and CEO, Cowbell. “We just closed our largest quarter to-date on the strength of omnichannel distribution, and with a focus on servicing our broker partners and policyholders. With this new investment, we will deepen our focus on serving our chosen markets in the U.S. and U.K. This milestone is a testament to our expertise, culture, and market leadership.”

Cowbell asserts that its momentum demonstrates its ongoing commitment to closing the insurability gap, and dedication to evolving as its customers’ needs evolve. Cowbell reports that it has a diverse set of reinsurance partners, spanning over 20 prominent reinsurers globally. The company characterizes its approach to assessing cyber risk and providing tailored, flexible coverage as the “underpinnings of its industry leadership.” The company says it has pushed its omnichannel strategy forward in 2023, which it says differentiates its distribution model from its closest competitors, bolstering its combined retail broker and embedded insurance channels by 14 percent in the last 12 months.

Cowbell says recognition validates the effectiveness of its approach. Cowbell Specialty Insurance Company (CSIC), Cowbell’s wholly owned subsidiary, has earned a Financial Stability Rating (FSR) of A, Exceptional, from Demotech, Inc. Last quarter, CBInsights recognized Cowbell as one of the top 100 private fintech companies globally, and the only Cyber Insurance provider on its annual Fintech 100 list. Earlier this year Amazon Web Services (AWS) named Cowbell to its Cyber Insurance Partner Initiative.

Cowbell Cyber Raises $100 Million in Series B Funding

Anthony R. O’Donnell // Anthony O'Donnell is Executive Editor of Insurance Innovation Reporter. For nearly two decades, he has been an observer and commentator on the use of information technology in the insurance industry, following industry trends and writing about the use of IT across all sectors of the insurance industry. He can be reached at or (503) 936-2803.

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