Jack Kudale

Founder, Chief Executive Officer and Chairman Cowbell

Last Reviewed: September 23, 2026

Executive Summary

Jack Kudale is the founder, chief executive and chairman of Cowbell, the Pleasanton, California insurer that sells cyber insurance, and increasingly technology errors-and-omissions and management liability cover, to small and mid-sized businesses. He started it in 2019 after a career in software and cybersecurity rather than insurance, and built the company around a premise that came from that background: that cyber risk can be assessed continuously from outside data rather than from a static questionnaire, so a policy can be priced and issued in minutes through brokers. Cowbell now says it protects about 30,000 businesses across the United States, the United Kingdom and Australia, has paid more than $275 million in claims, and has raised $202 million, including a $60 million Series C from Zurich Insurance Group in 2024.

Career Highlights

• Founded Cowbell Cyber Inc. in 2019; now its Founder, CEO and Chairman.
• Before Cowbell, led three venture-backed Silicon Valley cybersecurity and data analytics startups, after a long period as an executive in charge of distribution at a Fortune 500 software company.
• Closed a $20 million Series A in March 2021, led by Brewer Lane Ventures with Markel Corporation among the participants.
• Closed a $60 million Series C equity investment from Zurich Insurance Group in July 2024.
• In January 2026 set out a growth plan built on international cyber, financial lines, resiliency services, mid-market expansion and franchise subscriptions, and appointed John Botros as CFO.
• Testified as a witness before a House Homeland Security subcommittee in June 2024.

Professional Journey

Kudale was born and raised in India and moved to the United States at 18. He has described his route to Cowbell as engineer, then marketer, then sales executive, then chief executive, and then founder. His House witness biography fills in the outline, though not the names: a long stint running distribution at a Fortune 500 software company, followed by leading three venture-backed cybersecurity and data analytics startups in Silicon Valley, for about 25 years of business experience in all.

He founded Cowbell Cyber in 2019, with Trent Cooksley and Rajeev Gupta, now its chief operating officer and chief product officer, as co-founders. The opportunity he saw was on the supply side of a growing market. Most small businesses carried no standalone cyber cover, and the insurers who wrote it struggled to underwrite it at the speed and price small-business brokers needed. Cowbell’s answer was what it calls Cowbell Factors, a framework for continuously scoring cyber risk, and a platform that lets agents issue a policy in as little as five minutes. It operates as a managing general agent, backed by more than 25 insurance and reinsurance partners.

The company launched a program for agents to issue personalised cyber policies in September 2020, and in March 2021 closed a $20 million Series A led by Brewer Lane Ventures, with Pivot Investment Partners, Avanta Ventures and Markel Corporation participating. It then added Cowbell Resiliency Services, an incident response and cybersecurity advisory arm available to policyholders, and moved beyond the United States into the United Kingdom and later Australia. In July 2024 Zurich Insurance Group made a $60 million Series C equity investment, which Kudale called the strongest endorsement of Cowbell’s vision yet, and which brought total funding to $202 million.

In January 2026 Kudale framed the company’s next phase around operating profitability as well as growth, widening Cowbell from a cyber specialist into a broader provider across cyber, professional and management liability, and hiring John Botros, previously CFO of Resilience, as chief financial officer. The company then reported about 30,000 small and mid-sized policyholders, 60 percent of them with Cowbell for more than three years.

Outside the company, he has spoken widely on cyber insurance and the use of AI in underwriting, and in June 2024 he appeared as a witness before a subcommittee of the House Committee on Homeland Security. His congressional biography also records him as an EY Entrepreneur Of The Year Bay Area award winner.

Education

No education record was found in any source read.