The Future of Insurance Podcast – Trent Cooksley

Co-Founder & COO, Cowbell Cyber

Season 2, Episode 21, March 22, 2022

Guest Bio

Trent Cooksley is co-founder and COO of Cowbell Cyber. Cooksley is responsible for the strategic direction of Cowbell’s insurance operations and has built the company’s innovative cyber insurance portfolio along with its wide distribution network. As an insurance executive and three-time startup co-founder, Cooksley has held executive and investor roles in all stages of an insurance company’s growth. Prior to Cowbell, he was Head of Open Innovation for Markel Corporation and Managing Director of Markel Digital and brought to market numerous innovations such as the first pay-as-you-go insurance technology solution.

Highlights from the Show

    • Trent started his career in insurance at an early pioneer in the Workers Comp space in the early-2000s where he got to work across many different roles and functions
    • They sold that company to Markel, so he joined them, and helped form Markel Digital, Markel InsurTech Underwriters and Markel Digital Ventures
    • In 2019, he left and helped co-found Cowbell
    • Trent worked with Scott Whitehead at Markel, helping to support Thimble, which I wrote about in The Future of Insurance Volume II
    • The team at Markel looked at startups and InsurTech with an underwriter’s eye, which meant looking at the fundamentals of the insurance involved and the economics behind it
    • The other founders were going through the Global Insurance Accelerator on their idea for solving cyber insurance issues, and Trent was a mentor to them
    • Jack Kudale, co-founder and CEO of Cowbell, drove to see Trent to white board the idea after the GIA ended, and asked him to join the founding team
    • The team had a strong mix of technology and insurance expertise across the three of them
    • From Trent’s experience at Markel, he saw how certain barriers can be navigated more effectively, including how risk bearers who would back you think about risk so you can build your offering in a way that can work through things easier and faster
    • Trent learned the lesson clearly that you should have someone on the team who understands the depths of the industry in addition to outsiders who can think freely of it
    • While natural catastrophe modeling is much slower to change because of the speed of the dynamics in question, cyber catastrophe modeling and risk theory is changing daily, which is where Cowbell can find its advantage
      • They do a lot of scoring and modeling in-house to connect to how they want to look at the marketplace
      • They continuously monitor 23 million businesses in the US so they can take a real-time view on almost any risk that comes to them
      • Their approach is aimed at closing the information asymmetry at underwriting and at claim, and tying the feedback loops together so claims and underwriting learn from each other constantly
    • Many underwriters don’t tie internal feedback loops together to make product decisions in real-time, but they also don’t tend to use data that comes through their various operations since it’s not usually data so much as disassociated information held in a risk record or claim file
    • Cowbell thinks about all of this as they also look at risk engineering, to change the nature of the firm’s risk, not just for cyber, but more broadly because of the way technology pervades business
    • Cowbell is an MGA, but also has a captive so they can share in the risk with their capacity providers, which they feel is important
    • There’s been a shift in how the insurance market thinks about being a carrier or not
    • He does think there will be an evolution toward taking more risk because that is the insurer model, but it requires different disciplines and capabilities to make it work well
    • There’s disruption potential from insurtechs looking to take risk and avoid having other companies defining their product, but there are other constraints you come into when you go full-stack, too
    • Trent reminds us that insurance isn’t boring – it’s complex and important for protecting the entire world

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