Insurtech Cowbell to Focus on Mid-Market and Claims Processing with Key Appointments

Cowbell, a provider of adaptive cyber and specialty insurance solutions for small and mid-market risks, 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 experience in the insurance industry, recently serving as North America Middle Market Cyber Leader at WTW. During her career, she managed books of business across diverse industries, such as life sciences, healthcare, as well as manufacturing.

In her latest role, Klipphahn will be responsible for spearheading Cowbell’s continued expansion in the mid-market segment, reporting directly to Simon Hughes, leveraging her background in cyber and professional liability insurance.

Simon Hughes, SVP, Global Distribution & GM UK at Cowbell said that it is an opportune time to have Jessica build on her experience developing programs across diverse industries to help drive Cowbell’s growth in this market segment.

Stephanie Hewerdine brings experience working in the insurance industry, where she has supported insurance carriers in litigation and advisory roles, and offers a “blend of legal expertise and specialized cyber claims knowledge to Cowbell.”

Recently, she served as Claims Counsel at Coalition and has held senior positions at Sedgwick.

In her current role, Hewerdine will aim to support US claims, reporting to Mamta Birla, working with internal stakeholders, external parties, and regulatory organizations in order to enable the firm’s claims process and deliver customer service to brokers and insureds.

Mamta Birla, SVP & Head of Global Claims at Cowbel said that having supported Cowbell accounts in prior roles, Stephanie has seen their company’s commitment to client service, and claims-handling.

As reported earlier this year, Cowbell, a provider of cyber insurance for small and medium-sized enterprises (SMEs) and middle-market businesses, announced the launch of Cowbell COMPaaSSM (Compliance-as-a-Service), a new offering tailored for startups, growth-stage companies, and service providers handling sensitive customer data.



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Disclosure Quest

Reg A - Form 1-A Filings Beta

Beta. Initial Form 1-A only. Target raise is the stated Amount to be Raised, totaled. Compared with the same dates one year earlier.

YTD: Jan 1, 2026 - Oct 26, 2026 vs Jan 1, 2025 - Oct 26, 2025

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Number of Filings131Prior 126 +4.0%
Target Raise, Total$3.40BPrior $3.54B -3.9%
This YTDYear priorChange
Filings 131 126 +4.0%
Target raise $3.40B $3.54B -3.9%

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Source: DisclosureQuest. Initial Form 1-A only.

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This display counts initial Form 1-A filings only. It does not represent subsequent filings, including Form 1-A/A amendments or Form 1-A POS post-qualification updates filed by the issuer. Amounts are the stated Amount to be Raised on the initial filing, not capital raised and not amounts revised in later filings.

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