Cowbell Taps UK Architect Simon Hughes as CCO for Global Expansion

PLEASANTON, CA – January 15, 2026 – Cyber insurance provider Cowbell has appointed Simon Hughes as its new Chief Commercial Officer, a strategic move signaling an aggressive push to scale its global operations. Hughes, the architect of the company’s successful UK market entry, will now helm Cowbell's global commercial strategy, including distribution, partnerships, and international expansion, as the insurtech firm enters what it calls its “next cycle of growth.”

The promotion from his previous role as SVP, Global Distribution & GM, UK, places Hughes at the center of Cowbell's ambition to expand its adaptive cyber insurance model and achieve operational profitability. The appointment leverages his proven ability to establish and grow the company's footprint in new territories, a skill set deemed critical as the firm builds on its recent momentum.

“Simon has been instrumental in shaping Cowbell's international presence and elevating our commercial capabilities,” said Trent Cooksley, Co-founder & Chief Operating Officer at Cowbell. “As we enter this next phase of growth, his leadership across distribution, partnerships, and global market strategy will be critical to scaling responsibly while deepening our value to brokers and policyholders worldwide.”

The UK Blueprint for Global Growth

Hughes’s promotion is a direct result of his performance in the United Kingdom, which Cowbell now considers its “playbook” for future international expansion. After launching UK operations in the second quarter of 2023, the company reported staggering growth under his leadership. Between January and June 2024, Cowbell’s UK segment saw a 351% increase in premiums and a 327% rise in policies issued, supported by a 148% growth in its network of UK insurance agents and brokers.

This rapid success prompted the company to expand its UK offerings in January 2024, extending coverage to mid-market businesses with up to £1 billion in turnover. The UK strategy also included the rollout of key platform components, such as the Cowbell Prime One standalone cyber program and the Cowbell Rx cyber risk exchange marketplace, demonstrating the model's adaptability to new regulatory and market environments.

Before joining Cowbell in April 2023, Hughes honed his expertise at CFC Underwriting, where he led UK and EU cyber underwriting teams to achieve profitable growth. His new role as CCO tasks him with replicating this success on a global scale, starting with the company's recent expansion into Australia, announced as part of its new strategic cycle.

Charting the 'Next Cycle' of Growth

The appointment is a cornerstone of Cowbell’s “Next Cycle” initiative, a strategy announced in early 2025 focused on sustained growth, operational profitability, and global market penetration. The company has identified five key drivers for this phase: international cyber, financial lines, resiliency services, mid-market expansion, and franchise subscriptions.

This strategic push is backed by significant financial runway. Cowbell has raised a total of $209 million across six funding rounds, including a $60 million Series C in July 2024 led by Zurich. With this capital, the company has publicly stated its mission to achieve near-term operating profitability. This focus appears to be yielding results, with the company reporting a favorable 43% ultimate loss ratio for its 2022 book of business.

Cowbell's growth metrics underscore its market traction. The firm's new customer base grew by 49% year-over-year in 2023, and it currently protects around 30,000 small and mid-market organizations (SMEs) that represent a combined $610 billion in insured revenue. A strong 60% of these policyholders have remained with Cowbell for over three years, indicating high retention in a competitive market.

“Cowbell's growth over the past several years, from launching new markets to broadening our product and services portfolio, has been extraordinary. Leading the UK launch has been a career highlight, and I'm proud of the impact our team has made across the organization,” said Hughes. “As we move into this next cycle, I'm eager to help drive our global commercial strategy and continue building a platform that delivers protection with clarity, confidence, and scale.”

Beyond Insurance: The Rise of the Digital Protection Partner

Central to Cowbell’s strategy is its evolution from a pure insurance provider to a comprehensive “digital protection partner.” The company has pioneered what it terms “Adaptive Cyber Insurance,” which moves beyond static annual policies. Using its proprietary AI-powered platform and “Cowbell Factors,” it performs continuous risk assessment, allowing for policy issuance in as little as five minutes and dynamic adjustments to coverage.

This evolution is most evident in the launch of Cowbell Resiliency Services (CRS) in February 2025. This independent advisory arm integrates proactive cybersecurity services directly with insurance products. CRS offers subscription-based solutions, including:

• Cowbell MDR SOC-as-a-Service: A 24/7 US-based Security Operations Center providing threat detection and real-time response.
• Cowbell Penetration Testing-as-a-Service (PTaaS): On-demand internal and external network vulnerability assessments.
• Cowbell Cybersecurity Training-as-a-Service (CTaaS): Security awareness training and phishing simulations to strengthen the human element of defense.

To further this integrated approach, Cowbell has begun bundling its MDR solution into select Cyber and Tech E&O policies, offering deductible waivers as an incentive for adoption. In December 2025, the company launched self-service capabilities, allowing policyholders to activate these risk-management services directly from their dashboards.

Navigating a Volatile Cyber Market

Cowbell's strategic shift comes as the global cyber insurance market continues to mature and harden. The market is projected to reach $16.6 billion in 2025, with premiums expected to climb 15-20% annually. This growth is fueled by a relentless threat landscape, where ransomware remains dominant and AI-powered attacks are cited as the biggest future threat by over 60% of businesses.

In response, insurers are implementing stricter underwriting guidelines, often mandating controls like multi-factor authentication (MFA) and Endpoint Detection and Response (EDR) as prerequisites for coverage. Cowbell’s model is designed to address this reality, particularly for the SME sector. By providing a unified platform for Cyber, Tech E&O, and Management Liability, combined with continuous risk assessment and integrated resiliency services, the company aims to help businesses not only transfer risk but actively reduce it.

This closed-loop approach to risk management is becoming increasingly critical. As part of its forward-looking strategy, Cowbell's CRS unit recently introduced COMPaaS-AI, an AI governance and compliance service designed to help organizations navigate the complex regulatory landscape emerging around artificial intelligence systems, demonstrating a commitment to addressing the next frontier of digital risk.