How Adaptive Cyber Insurance Changes the Insurance Game

by | Sep 26, 2022 | Founders' Corner, Innovation, Podcast

As a special episode of this season, the first live-streamed video episode, we had Trent Cooksley, Co-Founder and COO at Cowbell, as a featured guest.

Trent’s career path took him from banking and bond trading to startups to the insurance space. He has focused particularly on the intersection of technology and underwriting, and how that could be part of the future of insurance. With accelerating digitization in the world, Trent became even more interested in cybersecurity, as well as the new risks associated with it. 

While Trent was on the board of the Global Insurance Accelerator, he met Jack Kudale, Cowbell’s Founder and CEO. In August 2019, Jack, Trent, and the other co-founders embarked on the journey of building Cowbell. 

From the outset, they wanted to create a platform that would adapt to changing environments, and find a way to “leverage an underwriting, distribution, risk management of cybersecurity platform to be more on top of identifying the exposures that were occurring in the marketplace and adaptive to how quickly those exposures were changing, and how those vulnerabilities were impacting corporations.”

Three years later, Cowbell has grown tremendously and made that goal a reality. By using cybersecurity tools, Cowbell is able to have deep visibility into organizations and compile Cowbell Factors using the extensive outside-in and proxy data to which Cowbell has access. We use Cowbell Factors to “score and benchmark an organization’s cyber risk and compare that to their peers so potential policyholders [have] a better understanding of where they [sit] within their security stack versus their peers, so they [can] see if they [are] going to be more of a target for threat actors or not.” 

Given how dynamic this technology truly can be when it comes to evaluating risk, Cowbell has now established itself as the champion of adaptive cyber insurance. In short, adaptive cyber insurance changes with cyber risk. “As these risks evolve, the intention is that coverages can evolve, policies can evolve, risk profiles can evolve and that we’re following the active risk at all times.”

For Cowbell policyholders, adaptive cyber insurance allows for improved risk profiles, better understanding of the threat landscape, and faster mitigation of vulnerabilities. Changes will occur within most organizations’ ecosystems as well, especially as new technologies are created and introduced, so it is important for policyholders to feel comfortable making these changes, knowing that their Cowbell cyber policies will adapt accordingly. 

Adaptive cyber insurance is unique in terms of the concept, the technology behind it, and the implementation. Most lines of insurance involve 6 or 12 month contracts that are underwritten once per year and then evaluated at the time of renewal. The issue is that over the course of 6 or 12 months, so much can change. Cowbell evaluates risk and exposure on a continuous basis – 24/7/365 – so there is no need to address changes retroactively. “We’d like our policyholders to sleep well at night knowing we are continuously assessing and adapting to the ever-changing threat landscape as well as the ever-changing landscape of those particular policyholders.”

Complementary to the launch of adaptive cyber insurance, Cowbell has officially become a full-stack carrier through Cowbell Specialty Insurance Company (CSIC). “Up until this point, Cowbell has operated as a Managing General Agent. We do from soup to nuts all the work within the lifecycle of an insurance policy. We partner with highly-rated reputable insurance carriers and reinsurers to help share in the risk that we take on for our policyholders.”

CSIC won’t change any of these relationships with reinsurers or partnerships with carriers. It will, however, allow Cowbell to be extremely innovative and forward-thinking, with more options that will adapt to evolving threats.

Trent closes with an important reminder: “Organizations all have a specific amount of risk around running [a] business and we want to help our policyholders be on top of that and just help the market continue to get better.” 

Our Founder and CEO, Jack Kudale, has also authored a blog on “The making of a tech-enabled full-stack insurer”.

To watch the full video version of Trent’s episode, please visit Cowbell’s LinkedIn, Facebook, or YouTube accounts. To hear Trent’s episode in full, please listen to the full podcast episode.

Visit the Cowbell Factor Podcast library to listen to last season’s episodes and subscribe to stay up to date on upcoming ones. It is available on most podcast platforms (iHeartRadio, Spotify, Google podcast, Apple podcast, Anchor and Radio Public). If you enjoyed this episode, consider rating it with 5 stars on Spotify and Apple!


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