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Oct 6, 2020

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Caroline Thompson is the Head of Underwriting at Cowbell Cyber, an AI-powered cyber security insurance for small and medium businesses. The company provides 24/7 risk analysis, individual coverage level, and underwriting services done in minutes. Beyond her position at Cowbell Cyber, Caroline is also one of the main authors of their company’s blogs. She covers topics on new state laws and regulations and the different coverages their company offers.

Caroline joins us to share how Cowbell Cyber works to determine a company’s risk for cyber attacks before it even happens. She describes how she wound up working in New York and explains the concept of microinsurance. She explains why cybersecurity policies are almost constantly updating and how their company leverages the Dark Web for possible attacks and risks. She shares what Silent Cyber Risks and Standalone Insurance mean in the context of a cybersecurity risk management company. Caroline also discusses what their company often recommends to improve the cybersecurity of their clients.

"A lot of packaged policies end up covering a little bit of cyber - but not the entire extent." - Caroline Thompson

Today on Spot On Insurance:

  • Caroline's work experience in New York and why she felt at home.
  • What microinsurance is and why Caroline made a senior thesis based on that topic.
  • The life decisions Caroline would have made differently in hindsight.
  • The best time to step away from a good, but stressful job.
  • The reason behind the company being named Cowbell.
  • The newer types of cyber attacks and how the insurance industry keeps up.
  • When insurers have to pay for claims for cyber losses for policies not designed for them.
  • Defining Silent Cyber Risks and Standalone Insurance.
  • Why companies should always opt for a standalone insurance for cyber security.
  • The changes Caroline sees in the industry regarding how they guard against cyber risks.
  • The security recommendations Caroline and their company provide to clients.

Key Takeaways:

  • If it's been six months and you've been unhappy with whatever it is you're doing, it's time to change.
  • A standalone insurance is ideal for covering all forms of cyber losses.
  • Customers need standalone insurance in order to clarify everything.

Connect with Caroline Thompson:

This episode was brought to you by…..

Insurance Licensing Services of America (ILSA), America’s Premier Insurance Compliance and Licensing experts. To learn more about ILSA and their services, visit

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