Cowbell Cyber Executives Recognized as Top 25 InsurTech Executives of 2021

Jack Kudale, Founder and CEO, and Rajeev Gupta, Co-Founder and CPO, Among Top Executives Driving Insurance Technology

PLEASANTON, Calif., December 29, 2021 – Cowbell Cyber, the industry’s first AI-powered cyber insurance provider for small to medium enterprises (SMEs), today announced its founder and CEO, Jack Kudale, and co-founder and CPO, Rajeev Gupta, have been named to the Top 25 InsurTech Executives by The Financial Technology Report. The Top 25 InsurTech Executives list highlights executives who bring to market innovative and secure solutions that provide businesses and individuals the best in insurance technology.

Jack Kudale founded Cowbell Cyber in January 2019 with the goal of making relevant, effective cyber protection accessible to organizations of every size while closing insurability gaps that take place over the lifetime of a policy. In July 2019, Rajeev Gupta joined as co-founder and CPO. Together, alongside co-founder Trent Cooksley, and Prab Reddy the Cowbell team has innovated at the crossroads of cybersecurity and insurance, two established industries with distinct cultures and operational approaches. Together, with their team of ‘Cowbellers’, they built the AI-based, continuous underwriting platform – the heart of Cowbell’s solution – to address the challenges long known to have hindered the adoption of cyber insurance: lack of accurate data, speed, transparency and insights.

“We are honored to be amongst great folks in the list of Top 25 InsurTech Executives. This recognition from The Financial Technology Report validates our mission at Cowbell to provide organizations of all sizes with financial protection against cyberattacks,” said Kudale. “We aim to help our customers monitor and remediate their cyber risk exposures and proactively improve their security.”

This year’s recipients include top performing executives across insurance compliance, cloud solutions, predictive analytics, and digitizing the customer experience, among other insurtech segments. Their leadership capabilities span product development, sales strategy, marketing, operations, technology, and other areas.

The full list of Top 25 InsurTech Executives of 2021 is available here.

Agencies can visit to get appointed with Cowbell Cyber and learn more about all available standalone cyber insurance programs.

About Cowbell Cyber
Cowbell Cyber provides standalone, admitted individualized, and easy-to-understand cyber insurance for small and mid-size enterprises. 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 to less than 5 minutes. Cowbell Insurance Agency is currently licensed in 50 U.S. states and the District of Columbia and provides SMEs with up to $5 Million in standalone coverage. For more information, please visit

Media Contact
John Kreuzer
Lumina Communications for Cowbell Cyber

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