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AiThority Interview with Jack Kudale, Founder and CEO at Cowbell Cyber

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AiThority Interview with Jack Kudale, Founder and CEO at Cowbell Cyber
Could you tell us about your journey in technology and how you started at Cowbell Cyber?

I have been in enterprise software for more than 25 years in various Technical and Sales roles. I was a global Head of Distribution for a large software provider in New York City and then led three cybersecurity startups in Silicon Valley for the five years prior to Cowbell Cyber. During that time, I saw three major themes in the cyber market:

  • First, the cybersecurity market has experienced significant growth but much of the spending is allocated to prevention and detection while response and recovery are left as an afterthought.
  • Second, cyber insurance is emerging as must have service for response and recovery and the market is growing substantially. But the insurability gap is widening, especially for small to mid-sized businesses.
  • Finally, although 200 carriers are active in offering cyber insurance products very few have established cyber practices, most of them are either reselling another company’s insurance product or selling cyber as an endorsement to another policy.

We saw the opportunity to provide standalone, modern, and data-driven insurance cyber coverage using Artificial Intelligence and other innovative technologies. This is why we founded Cowbell. Think of Cowbell, in the traditional sense, as an early detection signal where risk is transferred as the herd moves from one organization to the other – in our case from business to insurer to a reinsurer. Cowbell Cyber is a Managing General Agency backed by A-rated carriers and reinsurers, offering a Cyber Insurance product, “Cowbell Prime”, to SMEs. Cowbell Prime coverage can be quoted in minutes using a simplified application process and our patent-pending technology “Cowbell Factor”. Coverage is also underwritten with accuracy and speed using data and deep learning.

We actually go much further with modernizing the insurance process for cyber, especially the underwriting process. Cowbell continuously assesses and rates risk at a granular level organization by organization so that we can accurately select and price the cyber risk as it evolves. This can be done at the individual level, but also at the aggregated level simply because it is all based on the same data that, with Cowbell, is shareable throughout the insurance value chain.

Read More: AiThority Interview with Tomer Shiran, Co-Founder and CEO at Dremio

Our audience would like to know about your daily interaction with cybersecurity challenges and how you cope with these. Please tell us about it.

The effectiveness of cybersecurity programs has historically relied and still relies on three pillars:

  1. Technology: Investment and deployment of adequate cybersecurity tools;
  2. People: Awareness and training of employees;
  3. Process: Compliance to security controls as required by regulations, standards or best practices.

At Cowbell, even as a startup, we are no different than any other company. As a CEO, I have to reinforce daily that all three pillars are equally important. Changing people’s behavior towards security is probably the hardest but also the most important.

Also, because of the nature of what we do, I think it’s important to start thinking about a fourth pillar: Cyber Insurance. Billions of dollars are being invested every year in cybersecurity. Yet, no business feels more secure than five years ago. Cybersecurity is an absolute must but there will always be a residual risk. It is imperative for business to establish protection for residual risks and related losses through cyber insurance.

October was National Cybersecurity Awareness Month. How did you create awareness for your current and future customers? 

At Cowbell, we used our business and social networks during Cybersecurity Awareness Month to remind business partners that, unfortunately, there will always be resilient cyber risks. This was also an opportunity for us to educate our audience on how cyber insurance can be effective at mitigating financial losses due to incidents.

Which set of businesses and regions are more prone to cybersecurity incidents? Could you tell us about the most challenging cybersecurity event that you have studied/coped with? 

Cyberspace does not really have any geographical boundaries. But there’s no doubt that cyber threats is the unwanted byproduct of business digitalization. And businesses that process and store assets of value such as PII and PHI records have been and remain the primary target of cybercriminals.

2019 was a humbling year for all of us as cybersecurity professionals. We had to watch many cities falling victim of ransomware attacks, and companies like Capital One, who is known for its forward thinking approach to Cloud Computing and Cybersecurity, being victim of a major incident.

How do you see global IT and ITSM scenario evolving around cybersecurity protocols? Which technologies have been the biggest disruptors in this industry?

IT and the infrastructure behind IT operations have been completely disrupted and reinvented by the rapid adoption of cloud computing. This shift is an opportunity to revisit how we think about and deploy cybersecurity. New solutions that apply AI effectively emerge in every category of the security market. that can take over many of the repetitive tasks that have plagued security teams to date.

Would you agree that AI can successfully fill in for the cyber gap in the industry? 

I like to think that AI can bring tremendous efficiencies in cyber, enabling security professionals to really apply their expertise on being proactive and planning for every phase the cyber cycle. The NIST framework is a good one to follow: identify, protect, detect, respond, recover.

Let’s let the machines and AI focus on repetitive tasks, they are faster, more effective, and less prone to error than an overwhelmed security engineer team.

Read More: AiThority Interview with Thomas Saunders, Co-Founder at Nash

What are your predictions on the future of FinTech/InsurTech in 2019-2024? How can business owners safeguard against growing cybersecurity incidents?

Innovation is absolutely critical and will continue. Two data points to validate the trend: VC investment in Insuretech as more than doubled in the past 12 months. There is one other thing business owners need to think beyond prevention and detection. Its high time risk transfer strategies are implemented to mitigate losses in the aftermath of the security incidents. Cyber Insurance is one of the techniques to mitigate financial losses.

What is your opinion on “Weaponization of AI and Machine Learning”? How do you promote your ideas in the modern Digital economy?

AI and Machine Learning is being used by cyber criminals just like it’s being used by organizations for protection.

What kind of skills/technical specializations is Cowbell Cyber currently hiring for to support Product and Marketing teams? 

Cowbell sits at the crossroads of two gigantic markets, cybersecurity, and insurance. They operate differently but are both being disrupted by innovative technology and customer needs that are not being met today. So we’re looking for talents with experience in either of these fields with a strong will to challenge the status quo but are all good communicators to help our organization build the necessary bridges between the two fields. Currently, we are hiring for Business Development roles in 6 US states.

Finally, AI/Data Science is the linchpin of everything we do at Cowbell.

What digital technology start-ups and labs are you keenly following?

The list is long. In our core market, insurance, I pay a lot of attention to Lloyd’s Lab and the various initiatives they are pursuing to evolve their business. I am also keenly following innovation produced in Des Moines in the form of 4 accelerators, all headed by Women executives and operators, example, GIA by Nicole Gunderson, and Broker-Tech by Susan Hatten. Finally, I like the efficiency Boost Insurance is bringing into the market as an MGA in box with their A+ rated paper, and reinsurance panel.

What technologies within your industry are you interested in?

The insurance industry relies on a vast amount of data to estimate the probability and severity of cyber risks. Cyber insurance, more than any other line, relies on data. We believe that Artificial Intelligence and Machine Learning will drastically change all insurance core processes. AI’s ability to make sense of huge amounts of data should help refine and accelerate the modeling of cyber risks, enabling the entire cyber insurance ecosystem to rapidly mature and evolve at the same speed at the threat landscape.

As a tech leader, what industries you think would be fastest to adopting AI in car-making with smooth efficiency? What are the new emerging markets for these technology markets?

I find proprietary data, AI, and high efficacy risk-ratings factor as common threads between Cowbell Insurance (cyber) and Tesla Insurance (auto). Both models are similar in terms of our ability to continuously understand residual risk, be able to normalize the data and implement it in underwriting process. The Cloud adoption in enterprises is analogous to autonomous driving in auto industry, in terms that both are here are stay and grow but also hard to assess from risk perspective if using traditional methods to assess and underwrite. With ML and DL we have the ability to broaden the insurance coverages to address the insurability gaps.

What’s your smartest work-related shortcut or productivity hack?

I have theme days, I start each morning with major issues to resolve first and then go down the list in terms of its complexity. There are some days in the week I do not take any external calls. It keeps me and my team focused on what matters the most, for that day. I prefer to keep meetings at 25 or 50 minutes, with no more than 6 people. Our daily standups, 10 minutes at 10 am (10 on 10) which sometimes has a tendency to go for hours as we gear up for a launch.

Tag the one person in the industry whose answers to these questions you would love to read:

This is an easy question. I have had a great pleasure meeting Dan Keough, CEO of Holmes Murphy & Associates and be great to see his perspective on these questions. He is a true force in commercial brokerage and a leading voice behind broker-tech, newly created accelerator.

Read More: AiThority Interview with Paul Lipman, CEO at BullGuard

Thank you, Jack! That was fun and hope to see you back on AiThority soon.

Jack Kudale, a 26-year enterprise software veteran, founded Cowbell Cyber in 2019 with the aim to address cyber insurability gaps for small to medium enterprises. Previously, Kudale worked at CA Technologies (recently acquired by Broadcom) for 16 years as an executive in charge of distribution for distributed software globally. He also led 3 venture-backed silicon valley cybersecurity and data analytics startups in various stage-agnostic executive roles.

Jack is an avid student of emotional intelligence and serves as a governing board member of Brighter Children, a non-profit organization. He is a licensed property-casualty and surplus lines producer.

cowbell logo

Cowbell Cyber maps insurable threats and risk exposures using artificial intelligence to determine the probability of threats and impact on coverage types for the enterprise. In its unique approach to risk selection and pricing, Cowbell combines risk observability with cyber insurance using Cowbell risk-ratings factor to offer standalone, affirmative and individualized coverage.

As a result, small to medium enterprises (SMEs) can obtain insurance via brokers using simplified binding and expedited underwriting process. Cowbell Insurance Agency is a fully owned subsidiary of Cowbell Cyber and currently licensed in six states.

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