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

Cowbell delivers Prime Tech through an existing partnership with Obsidian, now providing customers with Technology E&O Primary coverage

PLEASANTON, Calif., April 23, 2024 – Cowbell, a leading provider of cyber insurance for small and medium-sized enterprises (SMEs), today introduces Prime Tech with Cowbell Co-Pilot, Cowbell’s artificial intelligence (AI) solution for efficient underwriting. Prime Tech is Cowbell’s adaptive cyber insurance offering that combines flagship Prime 250 cyber risk insurance with Technology Errors and Omissions (E&O) primary coverage. Prime Tech with Co-Pilot will help underwriters better assess risk and provide valuable insights to improve decision-making at speed, driving a 40% faster contract review time on average. 

To bring Prime Tech to the market, Cowbell is building on its four-year partnership with Obsidian Insurance Company, an A.M. Best rated “A-” excellent, hybrid program carrier, deepening its partnership to include Tech E&O primary coverage following Cowbell’s launch of Tech E&O excess in 2023. Prime Tech is available now to businesses with up to $250M in revenue in the US and provides limits of up to $5M.

“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,” said William Jewett, Chief Executive Officer of Obsidian. “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.”

“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,” said Trent Cooksley, Chief Operating Officer and Co-Founder of Cowbell. “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.”

To streamline the process and complexities of underwriting cyber and Tech E&O risks, Cowbell reveals Cowbell Co-Pilot, a generative AI solution built into the underwriting process of Prime Tech. Cowbell Co-Pilot leverages generative AI and Large Language Models (LLMs) to expedite the human review of contracts and guide the process with AI prompts that identify critical language important to verify prior to offering terms. 

Cowbell Co-Pilot’s benefits include:

  • Accuracy: By leveraging Co-Pilot to help analyze contracts, underwriters make more informed decisions. Co-Pilot highlights to underwriters key clauses, terms, and conditions that may impact the risk profile of the prospect, enabling underwriters to assess contract wording and risks more accurately.
  • Augmentation: Co-Pilot retrieves potentially relevant information from contracts and other sources to augment the underwriting process, leading to a more robust risk assessment by providing context and insights that may not be apparent solely from the contracts.
  • Communication: Co-Pilot generates clear summaries of contracts, making it potentially easier for human underwriters to communicate key feedback with broker partners and policyholders, thereby improving communication. 
  • Recommendations: Co-Pilot seeks to learn from each business it analyzes, in an effort to improve its ability to provide more relevant insights and recommendations over time. This allows Co-Pilot to suggest certain risk mitigation strategies, such as adding specific clauses to contracts.
  • Speed: Co-Pilot summarizes contracts, potentially saving underwriters time and allowing them to devote more time to other aspects of the underwriting process.

“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,” said Rajeev Gupta, Chief Product Officer and Co-Founder of Cowbell. “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.”

For more information about Cowbell, please visit

About Cowbell
Cowbell is a pioneer of Adaptive Cyber Insurance, a leader in providing small and medium-sized enterprises (SMEs) coverage adaptable to today’s and tomorrow’s threats and the advanced warning of cyber risk exposures. In its unique AI-based approach in risk selection and pricing, Cowbell’s continuous underwriting platform, powered by Cowbell Factors, compresses the insurance process from submission to issue in less than 5 minutes. Cowbell is backed by 25 prominent leading global (re)insurance partners and serves SMEs in 50 U.S. states, the District of Columbia and the United Kingdom. Founded in 2019, Cowbell is based in the San Francisco Bay Area with employees across the U.S., Canada, India, and the U.K. For more information, please visit

About Obsidian
Obsidian Insurance Holdings, Inc. is an insurance holding company with admitted and non-admitted insurance carrier subsidiaries that issue policies underwritten by managing general agents, managing general underwriters, and program managers. Obsidian sources, underwrites, and manages a diverse portfolio of property, casualty, and specialty insurance programs, and reinsures the majority of the business to select reinsurers. Obsidian was formed in 2020 in partnership with leading insurance industry executives and Genstar Capital. For more information, visit

Media Contact
John Kreuzer
Lumina Communications for Cowbell

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