Cowbell Expands Cyber Insurance Leadership with Strategic Mid-Market and Claims Appointments

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Cowbell, a provider of adaptive cyber insurance and specialty coverage for small and mid-sized businesses, announced two senior appointments to accelerate growth in North America and enhance claims operations. Jessica Klipphahn and Stephanie Hewerdine have joined the firm.

North America Mid-Market Expansion
Cowbell logo in blue representing the company's leadership in adaptive cyber insurance solutions for mid-market businesses

Jessica Klipphahn joins Cowbell as Head of North America Mid-Market, bringing over 15 years of experience in the insurance industry. She most recently served as North America Middle Market Cyber Leader at WTW, managing multi-million-dollar books of business across life sciences, healthcare, and manufacturing sectors.

Jessica Klipphahn joins Cowbell the  adaptive cyber insurance and specialty coverage provider as Head of North America Mid-Market
Jessica Klipphahn – Cowbell

Cowbell said Klipphahn will “spearhead continued expansion in the mid-market segment,” reporting to Simon Hughes, SVP, Global Distribution & GM UK. Her expertise in cyber liability insurance and professional coverage will support Cowbell’s growth in the mid-market insurance space.

Company Sees Growth Opportunity in Cyber Insurance and Tech E&O

“The middle market represents tremendous growth potential in cyber insurance and tech E&O,” said Simon Hughes. “Cowbell’s technology-driven approach and tailored coverage solutions position us perfectly to serve these complex business needs.”

Stephanie Hewerdine joins Cowbell the adaptive cyber insurance and specialty coverage provider as Director of Claims.
Stephanie Hewerdine – Cowbell

Cowbell’s adaptive insurance model continues to gain traction as cyber risks evolve. The company’s focus on innovation and automation supports scalable cyber coverage for businesses facing digital transformation challenges.

Stephanie Hewerdine Appointed Director of Claims to Strengthen Service Delivery

Stephanie Hewerdine joins as Director of Claims, offering 25 years of combined insurance and legal experience. She most recently worked as Claims Counsel at Coalition and held senior positions at Sedgwick.


Reporting to Mamta Birla, SVP & Head of Global Claims, Hewerdine will oversee U.S. claims processes, enhance client support, and ensure efficient coordination with regulatory bodies.

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Focus on Claims Leadership and Customer Experience

“Having previously supported Cowbell accounts in prior roles, Stephanie has seen firsthand our company’s commitment to innovation, client service, and claims-handling,” said Birla.

Cowbell emphasized that Hewerdine’s appointment strengthens its claims leadership, ensuring a faster, smarter, and more responsive claims experience for brokers and policyholders.

Cowbell Expands Its Adaptive Cyber Coverage Strategy

These appointments underscore Cowbell’s ongoing commitment to expanding its cyber coverage and strengthening leadership in a growing global market. The company continues to enhance resilience for small and mid-sized enterprises by integrating technology, data, and human expertise.

The adaptive approach keeps businesses protected against emerging cybersecurity threats, positioning the company as a leader in digital risk insurance solutions.

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