Cowbell Appoints Tim Regilio as Head of Western US Territory

PLEASANTON, California — January 22, 2025Cowbell, a leading provider of cyber insurance for small and medium-sized enterprises (SMEs), announced today the appointment of Tim Regilio as Head of the Western US Territory. Regilio has over two decades of experience in the insurance industry; most recently, he served as Director of Business Development at Sayata, where he played a key role in building the U.S. wholesale broker distribution network and spearheading new business initiatives. 

In his new role at Cowbell, Regilio will provide strategic direction and lead a sales team to drive revenue, expand market share, and forge strategic partnerships throughout the western US. He will report directly to Simon Hughes, Senior Vice President for Global Distribution, and will cultivate new business opportunities, manage key broker and partner relationships, and collaborate across teams to help grow and scale the business.

“We are thrilled to welcome Tim to the Cowbell team,” said Hughes. “His breadth of expertise in cyber and professional liability insurance, coupled with his proven track record of building and managing strategic partnerships to drive business development will be critical as we expand opportunities in the western U.S. His leadership will help us deliver on our commitment to help build resiliency for businesses as cyber threats continue to rapidly evolve in an increasingly digital world.”

With more than 20 years of experience in the insurance industry, Regilio brings a wealth of knowledge in cyber and professional liability coverages. Prior to Sayata, Tim was Head of Broker Relations in the northwest region for Beazley Insurance, managing select national broker relationships and driving growth for underwriting teams. He has also held senior roles at AIG and Principal Financial Group.

“I am excited to join Cowbell at such a pivotal time in the company’s journey,” shared Regilio. “Cowbell’s innovative approach to cyber insurance is making a tangible impact on the industry, and I look forward to collaborating with our partners to deliver exceptional value to our customers while expanding our footprint in the western U.S.”

 

About Cowbell
Cowbell is a pioneer of Adaptive Cyber Insurance, leading the way in providing small and medium-sized enterprises (SMEs) with coverage adaptable to today’s and tomorrow’s threats and the advanced warning of cyber risk exposures. With its unique AI-based approach in 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. Backed by 25 prominent global (re)insurance partners, Cowbell serves SMEs across 50 U.S. states, the District of Columbia, and the United Kingdom, assessing businesses with revenues up to $1B globally. Founded in 2019, Cowbell is based in the San Francisco Bay Area and has employees across the U.S., Canada, India, and the U.K.

For more information, please visit https://cowbell.insure/

Find Out How Cowbell Protects Businesses