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Cyber Insurance for SMEs: Faster Quotes with AI-Driven Underwriting

Posted on April 23, 2024April 23, 2024 By Martin Hinton

Cowbell Cyber, a leading provider of cyber insurance for small and medium-sized enterprises (SMEs), has introduced Prime Tech, a new insurance offering enhanced by Cowbell Co-Pilot, their AI-driven solution for streamlined underwriting. This innovative product merges their flagship Prime 250 cyber risk insurance with primary Technology Errors and Omissions (Tech E&O) coverage, designed to bolster risk assessment and expedite decision-making for underwriters.

Prime Tech touts Cowbell Co-Pilot as cutting contract review times by 40%, marking a significant improvement in underwriting efficiency. The offering is now accessible to U.S. businesses with revenues up to $250 million and coverage limits up to $5 million.

The rollout builds on Cowbell’s four-year partnership with Obsidian Insurance Company, an A.M. Best rated “A-” carrier. This collaboration has expanded to include primary Tech E&O coverage following Cowbell’s introduction of excess Tech E&O in 2023. William Jewett, CEO of Obsidian, expressed enthusiasm about deepening ties with Cowbell. “Deepening our partnership with Cowbell will provide greater cyber insurance solutions for insureds and offer a comprehensive insurance strategy for technology companies. We are proud to support them in that pursuit,” Jewett said. He also praised Cowbell’s consistent commitment, adding, “We believe strongly in Cowbell’s mission – and have since we entered our partnership four years ago. Their commitment to offering solutions for their clients creates a durable partnership and we are excited for the opportunities that will come with the growth of our relationship.”

Cyber Insurance For SMEs

Trent Cooksley, COO and Co-Founder of Cowbell, highlighted the integrated benefits of their new product. “Providing one policy that combines cyber with Tech E&O helps maximize contact points for the broker and the insured, solve for coverage overlap, and streamline claims processes,” Cooksley explained. He further stressed the significance of Tech E&O coverage in today’s risk environment: “Tech E&O primary, particularly paired with cyber insurance, is important to protect companies against rising threats and has been a highly requested product by our clients. We are thrilled to deepen our long-time relationship with Obsidian to deliver Prime Tech.”

Prime Tech embeds its generative AI feature, Cowbell Co-Pilot, into the underwriting process to elevate accuracy, enhance risk assessment, foster better communication, and boost speed. By generating contract summaries and highlighting crucial clauses and terms, Co-Pilot assists underwriters in making informed decisions and suggesting risk mitigation strategies, thereby enhancing productivity and precision for both technical and non-technical staff.

Rajeev Gupta, Chief Product Officer and Co-Founder of Cowbell, commented on the potential of their AI innovation: “We’ve leveraged AI in many forms to drive better outcomes for our customers and the company, but our latest innovation is going to be one of our biggest advancements to date. With underwriting Co-Pilot we can enhance productivity, efficiency, and precision within the decision-making processes for both technical and non-technical users, and therefore, bridge the gap between human expertise and technological capabilities.”

Source: Cowbell Introduces Prime Tech with Cowbell Co-Pilot, a Generative AI Solution to Optimize Underwriting Workflows.

Other News: AWS Moves Deeper Into Cyber Insurance-related Services, Adding Cowbell(Opens in a new browser tab)

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In this clip from our latest podcast episode, Dan Candee, CEO of Cork Protection, dives into a critical topic that hits close to home: Cybersecurity for Main Street businesses.

🛡️ With a background in enterprise-level cybersecurity on Wall Street and a personal connection to small business through his family, Dan shares why Cork focuses on protecting small and mid-sized businesses from rising cyber threats.

🚨 "The threat actors are getting better, and they're coming after Main Street more and more."

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🔗 Learn more about Cork: corkinc.com
🎧 Full Podcast Episode: www.youtube.com/@CyberInsuranceNews/podcasts

📣 Don't forget to LIKE, SUBSCRIBE, and hit the 🔔 notification bell so you never miss a powerful conversation.

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Cybersecurity for Main Street: Dan Candee on Protecting Small Businesses | CEO of Cork Protection
SMB Cyber Threats - In this episode of the Cyber Insurance News Podcast, host Martin Hinton talks with Dan Candee, CEO of Cork Protection, about the rising tide of cyber threats targeting small and mid-sized businesses (SMBs). Dan shares his journey from Main Street entrepreneur to cybersecurity leader, offering real-world insight into the threat landscape, financial vulnerabilities, and how AI and managed service providers (MSPs) can help fortify business resilience.

We explore:
• Why Main Street is more vulnerable than Wall Street
• Common SMB cybersecurity blind spots (like ACH fraud)
• The evolving role of managed service providers
• How Cork Protection blends cybersecurity and cyber insurance
• Real-world attack case studies and practical advice for SMBs

Whether you’re a small business owner, MSP, or cyber pro, this episode unpacks how to prepare, prevent, and protect your organization in today’s digital world.

📌 Topics: cybersecurity, cyber insurance, social engineering, SMB protection, ransomware, AI in security, MSPs

🎙 Guest: Dan Candee, CEO of Cork Protection
📢 Host: Martin Hinton, Executive Editor, Cyber Insurance News

👉 Don’t forget to like, comment, and subscribe for more insights on cyber insurance and digital defense!

#CyberSecurity #CyberInsurance #SMB #AI #CyberPodcast #BusinessResilience #smallbusiness #sme
00:00 Introduction - Dan Candee and Cork Protection
02:27 The Importance of Cybersecurity for Small Businesses
05:29 Understanding Cyber Threats and Their Impact
08:26 The Role of Managed Service Providers in Cybersecurity
11:24 24Financial Protection and Cyber Insurance Solutions
14:01 Leveraging AI in Cybersecurity
16:53 Navigating Cyber Insurance Policies
19:56 Empowering Small Businesses with Knowledge
21:52 The Future of Cybersecurity and Community Resilience
26:05 MSP/ MSSP The Lingo decoded
29:05 Finals Thoughts and a bit of Hope!
SMBs Are Cyber Targets | Dan Candee on Cyber Resilience & AI | Cyber Insurance News Podcast EP#6
Cyberattack on Small Business is on the rise—and AI is making it worse. In this episode of the Cyber Insurance News Podcast, host Martin Hinton sits down with William Altman of CyberCube to unpack how AI is enabling threat actors to more efficiently target and exploit small businesses.

🔐 From credential stuffing to brute force attacks, William explains how cybercriminals use AI to bypass login portals and MFA solutions—putting millions of small business owners at risk.

🎙️ Timestamps:
0:00 - Introduction
6:26 - William Altman on AI and threat actors
6:50 - Credential stuffing, brute force & reused credentials
10:00 - What small businesses can do right now
14:20 - The future of AI in cybercrime

🎧 Don’t miss this crucial update on the cybersecurity landscape for small businesses. Subscribe and stay informed.

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Cyberattack on Small Business: How AI Supercharges Cyber Threats | William Altman @CyberCube"
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