Inside-Out Data: Cowbell's Cyber Risk Assessment

Cowbell, a pioneer provider of cyber insurance for small and medium-sized enterprises (SMEs) and middle-market businesses.

It has expanded its Cowbell Connectors to over 30 integrations with top security and cloud service providers. 

Stronger security insights

Cowbell Connectors enhance cyber risk assessment and underwriting by drawing on inside-out dataWhile many businesses focus solely on outside-in or partial internal data, Cowbell Connectors enhance cyber risk assessment and underwriting by drawing on inside-out data, securely pulling real-time insights from:

• Cloud environments like AWS, Azure, and GCP
• Vulnerability scanners such as Tenable, Qualys, and Rapid7 InsightVM
• Endpoint security solutions like CrowdStrike, SentinelOne, and Sophos
  Identity and access management platforms such as Okta, Microsoft Entra, and Arnica
• Compliance-focused tools like Qualys Policy Compliance and Security Studio.

Reducing cyber risk

These newly expanded integrations - designed to be used as part of a multi-layered model including outside-in data, dark web intelligence, threat intelligence, loss cost and historical claims, and regulatory compliance - come in response to rising cyber attacks, with the U.S. among the countries with high data breach density.

Last year, there were over 6.85 billion known records breached in the U.S., while the average cost of a data breach amounted to 9.36 million U.S. dollars; figures Cowbell expects to rise this year, with advances in AI and geopolitical conflicts both contributing to increased risk. 

Strengthening cyber resilience

Rajeev Gupta, co-founder & Chief Product Officer at Cowbell, shared: “A 2024 survey among chief information security officers (CISO) in the US showed that almost 9 in 10 organizations were at risk of a material cyberattack in the following 12 months; damaging both reputation and bottom lines. It’s now 2025 and the situation is only worsening; AI advancements have continued, empowering cybercriminals to execute more adaptive and scalable attacks, while geopolitical instability is increasingly manifesting in cyberspace.”

“With threats evolving faster than ever, businesses must up their game. This is where - following the launch of our Cowbell Resiliency Services (CRS) unit in February this year - our expanded Cowbell Connectors come in, providing a 360-degree view of businesses’ security posture, bolstered by real-time inside-out insights.”

 Optimized cyber coverage

Cowbell’s proprietary, AI-driven risk ratings – policyholders pave the way for more precise underwritingBy feeding inside-out insights into Cowbell Factors - Cowbell’s proprietary, AI-driven risk ratings - policyholders can not only address and patch vulnerabilities quickly, but also pave the way for more precise underwriting, ensuring coverage accurately reflects the true level of risk exposure. 

Demonstrating strong internal controls to underwriters and improving risk rating over time can also result to lower premiums or more favorable coverage terms. 

Expanding cyber integrations

While businesses and brokers can explore the full suite of integrations in the Cowbell platform today, there are also plans to double its integrations this year, adding a further 30 connectors covering categories including cloud, email and endpoint security, third-party risk management, and SIEM (Security Information & Event Management) platforms. 

Keen to help support businesses in the best way possible, Cowbell has also said it is open to exploring new integrations based directly on the needs of its users.