Vanguard of a New Era: Three Indian Americans Among Top 25 InsurTech Executives

Three Indian Americans are among Financial Technology Report’s ‘The Top 25 InsurTech Executives.” The list names those who are “at the vanguard of a new era for the rapidly growing sector, as the next generation of businesses and consumers seeks the highest-quality insurance services that fit their needs for convenience and affordability,” the Financial Technology Report said. 

“Already well known and staying current with technology trends, the companies represented on the list are poised to ascend as major players across a global market which is projected to reach $11.9 billion by 2027,” the report added. “With these leaders more than capable of adapting their operations as industry trends dictate, the evolution of InsurTech will mean record business for their enterprises.”

Indian Americans on the list include Art Agrawal, co-founder and CFO, Jerry, the car ownership super app; Jack Kudale, founder and CFO, Cowbell Cyber; and Rajeev Gupta, co-founder and Chief Product Officer, Cowbell Cyber. 

Art Agrawal’s Jerry was born of his desire to eliminate hassle from his own frustrating, expensive, and time-consuming experiences with car insurance, financing, repair, maintenance, warranties, and parking. He and his co-founders first disrupted the century-old car insurance process and launched Jerry’s AI and ML-based insurance comparison service in 2019. “Today, the company saves more than 1.5 million customers an average of $850 per year, making Jerry the #1 rated and most downloaded app in its category,” the report said. “Agrawal leads with a relentless focus on the customer experience as the company builds additional marketplaces to save customers time and money on all areas of car ownership.” Previously, he had founded on-demand car repair services provider YourMechanic, the 2012 winner of TechCrunch Disrupt. As CEO, the Drexel University alumni grew YourMechanic to the largest company in its industry, with more than 2,000 mechanics across the U.S. 

Cofounded by Jack Kudale and Rajeev Gupta, Cowbell Cyber is the industry’s first AI-powered cyber insurance provider that aims to make cyber insurance accessible to all businesses. Under their leadership, the company has racked up several awards for outstanding performance in 2021. 

Kudale brings 25 years of business experience, having led three venture-backed Silicon Valley cybersecurity and data analytics startups after a long stint as an executive in charge of distribution at a Fortune 500 software company. He is a frequent speaker at industry events covering topics such as the future of cyber insurance and the use of AI and technology to enable continuous underwriting for cyber. Kudale earned an engineer’s degree in electronics and telecommunications engineering from the University of Pune

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Gupta has 20 years of hands-on experience in software architecture and the design of large-scale, secure enterprise applications. He was the GM for the Application Protection business unit at Zimperium, a leader in mobile security. Previously, at CA Technologies, he was the head of product for the Application Delivery BU, where he mentored several customer teams and led efficient software development strategies for Fortune 500 clients.

Gupta is a judge, mentor, and coach for the international youth organization FIRST in addition to volunteering his free time teaching kids advanced electronics, robotics, and hands-on IOT projects. He earned a Bachelor of Engineering in electronics and communication from the Netaji Subhas Institute of Technology and a Master of Business Administration in finance and marketing from Santa Clara University’s Leavey School of Business.