#United States #Pleasanton, California #Cyber Insurance #Cowbell #Simon Hughes

Cowbell Appoints Simon Hughes as Chief Commercial Officer

Cowbell, the prominent provider of adaptive cyber and specialty insurance solutions, has made a significant announcement regarding its leadership. On January 15, 2026, it was revealed that Simon Hughes has been appointed as the new Chief Commercial Officer (CCO). In this key role, Hughes will spearhead Cowbell's global commercial strategy, with a particular focus on distribution, partnerships, international growth, and market development.

Hughes previously served as the Senior Vice President of Global Distribution and General Manager for the UK. Since joining Cowbell, he has played a vital role in the company's expansion efforts, particularly in bringing Cowbell’s innovative solutions to the UK market. His efforts have been instrumental in establishing Cowbell's presence and enhancing its distribution ecosystem internationally. With this new position, he is poised to catalyze the next phase of Cowbell's growth trajectory, which emphasizes sustained operational profitability and ongoing global expansion.

Trent Cooksley, Co-Founder and Chief Operating Officer of Cowbell, expressed confidence in Hughes' appointment, stating, "Simon has been pivotal in shaping Cowbell's international profile and enhancing our commercial capabilities. His leadership in distribution, partnerships, and global market strategy will be essential as we responsibly scale and deepen our value for brokers and policyholders worldwide."

In his own words, Hughes reflected on his career, stating, "The growth Cowbell has achieved over the years, from launching new markets to broadening our array of products and services, has been nothing short of remarkable. Leading the UK launch was a career highlight, and I take pride in the contributions our team has made to the organization. As we embark on this new chapter, I am excited to help steer our global commercial strategy and continue building a platform that provides clear, confident, and scalable protection."

The appointment follows Cowbell’s impressive momentum in the insurance sector, transitioning into a more comprehensive digital protection partner, and venturing into new international markets. To date, Cowbell collaborates with over 35,000 producers globally and is actively growing its risk pool, product offerings, and international reach as it enters this next strategic growth phase.

About Cowbell

Founded in 2019 and headquartered in the San Francisco Bay Area, Cowbell has pioneered Adaptive Cyber Insurance, redefining risk transfer for the digital age. The company has developed the first platform to integrate Cyber Insurance, Technology Errors and Omissions, and Management Liability into a single, API-driven solution. Cowbell aims to streamline the insurance purchasing journey, enabling policy issuance in as little as five minutes, utilizing its proprietary AI-powered platform and approach known as Cowbell Factors™. The company serves businesses with revenues up to $1 billion, operating across all 50 U.S. states, Washington D.C., and the UK. Backed by more than 25 leading global (re)insurance partners, Cowbell offers a comprehensive suite of coverage in commercial and specialty lines, including cyber protection and management liability. Additionally, Cowbell Resiliency Services (CRS), its independent cybersecurity advisory wing, provides policyholders access to Digital Forensics and Incident Response (DFIR) services, aiming to reduce risk exposure and enhance insurability. With teams positioned across the U.S., Canada, Australia, India, and the UK, Cowbell is at the forefront of innovation in cyber risk management worldwide.