Cowbell Cyber Raises $20 Million In Series A Funding

The rapidly growing distributor will use the funding to scale its AI-powered cyber insurance offering.

(Image source: Cowbell Cyber website.)

Cowbell Cyber, a Pleasanton, Calif.-based startup insurance distributor using artificial intelligence (AI) to underwrite insurance for small to medium enterprises (SMEs), has announced that it has closed $20 Million in Series A funding to scale its offering for continuous underwriting and closed-loop risk management. Brewer Lane Ventures (Boston) led the investment with participation from Pivot Investment Partners, Avanta Ventures, Markel Corporation, and existing investors ManchesterStory, Tri-Valley Ventures, and Holmes Murphy. The new capital will be used to fund product development, expand risk engineering, sales, marketing, and increase Cowbell’s footprint nationwide.

The company also announced that Martha Notaras, Managing Partner, Brewer Lane Ventures, will join the Cowbell Board of Directors and Akbar Poonawala, Co-Founder, Pivot Investment Partners, will join as a board observer.

Jack Kudale, Founder and CEO, Cowbell Cyber.

This investment follows Cowbell Cyber’s September 2020 launch of its Prime 250 program, which lets insurance agents issue personalized cyber policies—a program that has since expanded to 38 states. Cowbell Cyber says that it will continue aggressively growing its risk pool of 10 million continuously monitored organizations and its network of more than 4,500 agents and brokers that now distribute all of Cowbell’s cyber insurance programs. Cowbell reports that its precision in underwriting and speed in the distribution has helped the company achieve 1,595 percent growth in premium run-rate since then, making it the fastest-growing cyber insurance provider in the industry, which is projected to grow fourfold from 2018 to reach a value of more than $20B by 2025.

“Cybersecurity is now a risk management issue that is critical to the future of the insurance industry and is evolving at a pace that insurers have rarely seen,” comments Jack Kudale, Founder and CEO, Cowbell Cyber. “Cowbell Cyber has capitalized on businesses’ accelerated digitization and an ever-changing threat landscape. Cowbell embraces AI and machine learning to gain efficiency and accuracy when assessing and underwriting cyber risk while focusing on the fundamental needs of our policyholders: keeping their businesses protected from evolving cyber threats.”

Empowering Policyholders to Be Proactive in Managing Cyber Risk

Martha Notaras, Managing Partner, Brewer Lane Ventures.

Cowbell’s AI-powered standalone and tailored programs protect businesses from cyber threats that cripple an infiltrated business, a company statement says. As the threat landscape intensifies, business interruptions that result from ransomware attacks are up 20 percent, lasting up to 19 days, which, for many organizations, leads to a complete shutdown due to overwhelming costs. Cowbell Cyber’s says its closed-loop approach to cyber risk bundles cybersecurity awareness training, continuous risk assessment, and pre- and post-breach risk improvement services. Its cyber policies are designed to empower policyholders to be proactive about managing cyber risks.

“Through its cutting-edge, AI-powered platform, Cowbell Cyber is well-positioned to disrupt today’s explosive cyber insurance market and redefine the industry,” comments Martha Notaras, Managing Partner, Brewer Lane Ventures. “As the marketplace continues to see significant growth, we are thrilled to be joining the organization at a time in their journey where they are seeing unrivaled traction, and have put together a world-class team, staking a claim as a dominant force in the industry.”

Cowbell’s continuous risk assessment services, Cowbell Factors, are available free, on-demand to all businesses at

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Anthony R. O’Donnell // Anthony O'Donnell is Executive Editor of Insurance Innovation Reporter. For nearly two decades, he has been an observer and commentator on the use of information technology in the insurance industry, following industry trends and writing about the use of IT across all sectors of the insurance industry. He can be reached at or (503) 936-2803.

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