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Electronic Chat with Trent Cooksley, COO and Co-Founder, Cowbell Cyber

According to the FBI’s Internet Crime Complaint Center, cyberattacks have increased by 300% since the start of the COVID pandemic last spring. For businesses, this is an ongoing threat. Last year, the average business cost of a cyberattack was $3.86 million and it takes over 200 days to detect the breach, according to IBM.

Cowbell Cyber, based in Pleasanton, Calif., enables “cyber insurance 2.0” by delivering a vertically integrated cyber insurance solution. Outside-in and inside-out risk assessment combined with AI-powered cyber risk modeling and underwriting provides the ability to issue customized cyber policies written on the industry's most robust and admitted cyber coverage forms. Policyholders benefit from a transparent buying experience, a policy tailored to their unique needs, and recommendations and services to remediate identified risks.

Cyber risk is an ongoing concern for all business. How has the availability of big data from multiple sources changed the game for the cyber insurance market?

The ability to inject richer datasets into the assessment of individual cyber risk contributes directly to a more refined underwriting process. When blended with AI-powered processes, risk selection and pricing can be based on hundreds of observations and account for all available data in the risk pool. Overall, this results in faster but more precise underwriting, while also eliminating bias and errors.

Everybody benefits: using data and precise underwriting, policies can be customized; brokers can serve their clients faster; insurers get a better handle on their risk portfolio, and policyholders can get more value through the individual risk assessment they receive as part of the process.

Cowbell recently raised $20 million to improve AI capabilities in data collection and more. What are these and future funds earmarked for within the company?

Cyber threats are constantly evolving. The current wave of cybercrime and ransomware attacks is impacting businesses nationwide across all classes of business, regardless of size. Cowbell’s plan is to keep augmenting the data and risk pool we rely on for underwriting, while developing further the closed-loop risk management services we provide to our policyholders.

The drive to add value to policyholders on top of the insurance policy is why we are focused on onboarding new partners across the insurance, security, and services ecosystems. This is in line with the recent New York Department of Financial Services framework for cyber insurers and we’re excited to have recently launched Cowbell Prime, our admitted insurance program, in the state of New York.

Finally, we take pride in our distribution network and will continue to expand it, but also help our appointed agents and brokers succeed with building a new line of business around cyber.

What challenges do insurtech startups face in the investment process?

Insurance is still in the early stages of some significant innovation. At every step of the process, using technology, data and automation brings a better user experience, significant efficiencies, and also better visibility into the entire insurance process. Insurtech startups need clarity of focus and operational discipline to take their innovation to fruition. 

Please share your background and how it influenced your involvement with Cowbell.

I started my career at an early-stage work comp insurance company focused on data and technology. I was Head of Open Innovation and Managing Director at Markel for many years prior to founding Cowbell. I was lucky to be in the early stages as a partner and investor to some of the most dynamic insurtechs and carriers in the space over the years. I try to bring the best of both worlds to the table at Cowbell, what a good incumbent insurance company does well and what a nimble startup does well. Cyber is really exciting because of the unique challenges that need to be solved, both technically and from an underwriting perspective as well as the organic growth nature of the line.

What developing trends are you seeing in cyber risk?

The digital footprint of businesses has exploded in the past 18 months, but the deployment of cybersecurity has too often been lagging. For example, the sudden shift to remote work because of the pandemic has left many organizations exposed, with employees using non-encrypted personal WIFI networks to connect to work.

With attacks such as ransomware or invoice manipulation, cyber criminals can launch profitable operations on any industry. There is a dire need for every business to understand their risk profile, identify exposures, and remediate any weakness.

The approach we develop at Cowbell compiles a risk profile in real time and brings to the policyholder a wealth of information and resources to help mitigate risk, deploy incident response plans, and raise employees’ cybersecurity awareness.

Especially in the wake of COVID, more companies rely on contractors to operate. What are the unique challenges faced by both companies and contract workers regarding cyber risk – and how can Cowbell help mitigate the risk?

Remote work has flourished under COVID, enabling many businesses to tap into talent pools such as contractors that they did not consider before. Along with business email, suppliers and third-party vendors are known to be a challenge for cybersecurity. Our platform is open and we invite policyholders to ask their contractors to understand their risk profile using Cowbell. We are also in the process of activating new data sources to develop innovative risk ratings and go deeper into the supply chain when establishing the risk profile of an organization.


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The Email Chat is a regular feature of the ITA Pro magazine and website. We send a series of questions to an insurance IT leader in search of thought-provoking responses on important issues facing the insurance industry.


April 5th – 7th, 2020
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