Cowbell appoints Klipphahn & Hewerdine to strengthen mid-market and claims operations
- October 29, 2025
- Posted by: Beth Musselwhite
- Category: Insurance
Cowbell, a cyber and specialty insurance provider focused on small and medium-sized enterprises, has announced the appointments of Jessica Klipphahn as Head of North America Mid-Market and Stephanie Hewerdine as Director of Claims.
In her new role, Klipphahn will lead Cowbell’s continued expansion in the mid-market segment, reporting to Simon Hughes, Senior Vice President (SVP), Global Distribution & GM UK at Cowbell.
She brings over 15 years of industry experience, joining from WTW, where she most recently served as North America Middle Market Cyber Leader, overseeing a team of Cyber & Professional brokers delivering comprehensive insurance programs.
Prior to that, Klipphahn spent eight years at Odell Studner in senior roles, most recently as an Account Executive, responsible for the strategic oversight and servicing of a large middle-market book of general business.
Earlier in her career, she held positions at ECBM Insurance Brokers & Consultants and The Hartford.
Hughes commented, “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.
“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.”
As Director of Claims, Hewerdine will support US claims, working closely with internal stakeholders, external parties, and regulatory bodies to enhance Cowbell’s claims process and deliver high-quality service to brokers and insureds. She will report to Mamta Birla, SVP & Head of Global Claims at Cowbell.
Hewerdine brings 25 years of industry experience, having supported insurance carriers in litigation and advisory roles, with deep legal expertise and specialised cyber claims knowledge. She joins Cowbell from Coalition, where she served as Claims Counsel.
Before that, she was Claims Manager (Team Lead), Professional Liability at Sedgwick, managing a team of attorney claims professionals handling Cyber, Tech E&O, Media Liability, D&O, and LPL claims.
Birla said, “We’re thrilled to have Stephanie joining Cowbell at such a pivotal time as the cyber insurance industry continues to evolve.
“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.”


