Pleasanton, Calif., October 23, 2025 – 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.”
