Cowbell Announces Strategic Appointments to Advance Mid-Market and Claims Leadership

Jessica Klipphahn and Stephanie Hewerdine Join Cowbell to Drive Growth Across the North America Mid-Market Segment and Enhance Claims Experience

PLEASANTON, Calif., Oct. 23, 2025 /PRNewswire/ -- Cowbell, a leading provider of adaptive cyber and specialty insurance solutions for global small and mid-market risks, today announced it has strengthened its market position and operational capabilities by appointing Jessica Klipphahn as Head of North America Mid-Market and Stephanie Hewerdine as Director of Claims.

Jessica Klipphahn brings over 15 years of experience in the insurance industry, most recently serving as North America Middle Market Cyber Leader at WTW. Throughout her career, she has managed multi-million-dollar books of business across diverse industries, including life sciences, healthcare, and manufacturing.

In her new role, Klipphahn will spearhead Cowbell's continued expansion in the mid-market segment, reporting to Simon Hughes, leveraging her extensive background in cyber and professional liability insurance.

"We're thrilled to have Jessica join Cowbell to lead the expansion of our mid-market capabilities. The middle-market represents tremendous growth potential in cyber insurance and tech E&O, and Cowbell's technology-driven approach, alongside tailored coverage solutions and our market-leading claims and incident response capability, positions us perfectly to serve these complex business needs," said Simon Hughes, SVP, Global Distribution & GM UK at Cowbell. "It is an exciting time to have Jessica build on her experience developing multi-million dollar programs across diverse industries to help drive Cowbell's continued success in this critical market segment."

Stephanie Hewerdine brings a combined 25 years of experience working in the insurance industry, where she has supported insurance carriers in litigation and advisory roles, and offers a unique blend of legal expertise and specialized cyber claims knowledge to Cowbell. Most recently, she served as Claims Counsel at Coalition and has also held senior positions at Sedgwick.

In her new role, Hewerdine will support US claims, reporting to Mamta Birla, working closely with internal stakeholders, external parties, and regulatory bodies to drive the company's claims process and deliver market-leading customer service to brokers and insureds.

"We're thrilled to have Stephanie joining Cowbell at such a pivotal time as the cyber insurance industry continues to evolve," said Mamta Birla, SVP & Head of Global Claims at Cowbell. "Having previously supported Cowbell accounts in prior roles, Stephanie has seen firsthand our company's commitment to innovation, client service, and claims-handling. We're excited to have Stephanie leverage her experience to enhance Cowbell's claims team and deliver exceptional support to our policyholders when they need it most."

About Cowbell
Cowbell is a pioneer in Adaptive Cyber Insurance, redefining risk transfer for the digital age. As the first platform to unify Cyber, Tech E&O, and Management Liability into a single, API-driven solution, Cowbell expedites the insurance purchasing process, with policy issuance in as little as five minutes through its proprietary, AI-powered platform and Cowbell Factors™—a dynamic framework for continuous risk assessment. Serving businesses with up to $1 billion in annual revenue, Cowbell operates across all 50 U.S. states, the District of Columbia, and the United Kingdom. The company is backed by over 25 leading global (re)insurance partners, offering a comprehensive suite of coverages in commercial and specialty lines, including cyber, technology errors and omissions, and management liability. Through Cowbell Resiliency Services (CRS)—an independent cybersecurity advisory arm—policyholders gain access to Digital Forensics and Incident Response (DFIR) services as well as proactive solutions designed to reduce risk exposure and improve insurability. Founded in 2019 and headquartered in the San Francisco Bay Area, Cowbell has a global presence with teams across the U.S., Canada, Australia, India, and the U.K., driving innovation in cyber risk management worldwide.

Media Contact
Christian Morley
ICR for Cowbell
[email protected]

SOURCE Cowbell Cyber, Inc.