SalesTech Star

SalesTechStar Interview with Caroline Thompson, Head of Underwriting at Cowbell Cyber

Sales and marketing leaders need to be adept at helping businesses mitigate online cyber threats today, Caroline Thompson, Head of Underwriting at Cowbell Cyber shares some best practices:


Hi Caroline, we’d love to hear about your journey through the years…tell us more about your role at Cowbell Cyber.

I have been in insurance all my working life. Before joining Cowbell Cyber in 2019, I worked at Zurich, Argo, and Beasly, among others. I learned a lot about underwriting working for those companies but decided to join Cowbell because the insurance industry is known to evolve slowly, and I wanted to be part of a company that uses cutting-edge technology to disrupt the market. As Head of Underwriting, I manage all underwriting functions, from defining and filing coverages state by state, to developing underwriting guidelines and overlooking our AI-assisted underwriting process.

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Can you share your thoughts on some of the biggest cyber threats affecting online services today?

Cloud services – SaaS applications or cloud infrastructure – are easily misconfigured. It can be difficult for untrained employees to set up those environments for security best practices, and human error happens a lot. Unfortunately, these mistakes expose businesses to risk and present opportunities for cybercriminals to compromise assets. As everybody is aware, the surge in ransomware attacks is one of the biggest cyber threats right now, but we should anticipate new forms of threats as IoT technologies become mainstream and businesses accelerate their digitization.

What according to you are some best practices that business leaders need to keep in mind to mitigate risks here?

Especially in the market that we are focusing on, which is businesses with revenues of up to $1 Billion, cyberattacks are opportunistic. Cybercriminals do not target specific companies. Instead, they are targeting the error made by employees when deploying digital assets. The best way to mitigate such risk is through basic security hygiene, forcing the use of MFA, changing default passwords, training employees to recognize malicious behavior and phishing emails. Overall, applying cybersecurity best practices can be effective at stopping cyberattacks for the time being.

Can you talk about the more sophisticated techniques that leading sensitive industries (finance, etc) use to reduce data thefts and cyber risks?

There’s a myriad of cybersecurity tools that can be deployed. Some of the most advanced use machine learning techniques that detect abnormal behavior in digital environments. There are also more straightforward techniques such as using segmentation and privileged access controls on critical systems. Only giving users access to the systems and the data they really need minimizes the exposure of sensitive data within an organization.

How do you feel cyber security platforms will evolve over the years and in the near-term?

Cybersecurity will certainly evolve to automate security repetitive tasks. AI-assisted security and the use of artificial intelligence to detect abnormalities and pre-digest whether those present significant risks is becoming mainstream. This is similar to what we do at Cowbell Cyber with the use of AI-assisted underwriting.

A few thoughts last takeaways for business leaders suited to today’s environment.

Digital innovation is accelerating and deploying security best practices along with training employees on cybersecurity awareness upfront in all digital initiatives is important. It pays off automatically, less exposure to cyber threats, a streamline cyber insurance process and most importantly, a more secure business.

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Cowbell Cyber is an MGA dedicated to cyber insurance. Cowbell makes cyber insurance 2.0 a reality enabling quoting and underwriting at speed while delivering clarity of coverage and enabling policies to be easily customizable to match every client’s unique needs.

Cowbell Factors, the company’s proprietary multi-variant risk rating factors, are compiled in real-time, combining outside-in and inside-out data to anchor precise and unbiased underwriting at speed. Policyholders benefit from a transparent buying experience, a policy tailored to their unique needs and written on the industry’s most robust and admitted forms, and value on day one with recommendations to remediate identified risk exposures.

Caroline Thompson is Head of Underwriting at Cowbell Cyber. Caroline has 11 years of insurance experience including claims and underwriting for cyber. She has held various roles at Beazley and Argo. While working for a Lloyd’s Syndicate, she was able to complete her Award in London Market Insurance. Most recently, Thompson was a Senior Underwriting Specialist at Zurich on the Middle Market Specialty and E&O team underwriting E&O and cyber business for fast growth businesses. At Zurich, she built out the West Coast team targeting businesses up to $750M in revenue.

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