Community//

Jack Kudale of Cowbell Cyber: “Innovation always comes with some form of disruption to established ways of doing business”

Resilience and grit are two qualities critical to building a business from a ground-up. On the startup journey, you will meet more people who will offer a multitude of reasons why your endeavors will fail than people who will support you. Use your own filter not theirs to decide what path to take, and build […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

Resilience and grit are two qualities critical to building a business from a ground-up. On the startup journey, you will meet more people who will offer a multitude of reasons why your endeavors will fail than people who will support you. Use your own filter not theirs to decide what path to take, and build a community of advisors around you that brings a balanced view over what you’re trying to achieve with advice to overcome roadblocks.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Jack Kudale.

Jack Kudale is Founder and CEO at Cowbell Cyber. Jack brings over two decades of business executive experience. Previous senior roles include: COO at Cavirin, CEO at Lacework, both cloud security startups; SnapLogic, a leader in hybrid cloud integration; and CA Technologies, where Kudale led DevOps sales for the Fortune 500 leader. With deep operational experience in the DevOps, Cybersecurity, IT Ops, & Big Data spaces, Jack leads Cowbell to execute on its vision of bridging the cyber insurability gap. Jack also serves as a governing board member of Brighter Children, a non-profit organization.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

My first job was to repair manufacturing robots when I was 18. I am an engineer turned product manager turned sales executive turned CEO turned entrepreneur. After a long 25 year career in software, in Jan 2019, I packed my bags and went to Des Moines, Iowa from Silicon Valley, where me and family currently reside, to validate hypotheses on cyber insurance and decide on a business model. It seemed that cyber as an insurance line of product was still underwritten only once a year and was based on industry, revenue and employees. For the problem to solve it required two industries to come together — insurance and cybersecurity. Cowbell’s journey began on this premise and it is a very complex problem to solve and also hard one to repeat.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Cowbell is innovating at the crossroads of cybersecurity and insurance, two established industries with distinct cultures and operational approaches. Rather than just patching together the best of the two, we are building new offerings to address the challenges known to have hindered the adoption of cyber insurance: lack of accurate data, speed, transparency and insights.

The lifeblood of insurance underwriting is data — so we decided to start with the vast amount of security observations already available inside and outside an organization and apply machine learning to normalize it and make it usable for risk quantification and insurance. With an unparalleled amount of data at hand, we produce Cowbell Factors, our unique set of risk ratings that quantify threats and risk exposure for each organization. This is the foundation on which we build a continuous underwriting process and accurately assess, select and price cyber risk. With Cowbell, cyber policies are no longer written based on company size and industry alone and using a one-size-fits-all model.

Using modern technologies, we have been able to build our platform in six months, automating the many steps that were paper-based. Everybody benefits from an expedited process that can be completed in 5 minutes.

Bringing transparency to cyber insurance was also important to us. All stakeholders have access to our platform, with a view relevant to their role in the process. Agents can view clients’ risk exposure, compare it to other accounts in their portfolio, and customize our pre-packaged coverages before presenting to their client. Re-insurers get risk portfolio data in one place with the ability to analyze it dynamically across numerous variables.

Most importantly, policyholders can manage their policy online, view their Cowbell Factors with industry benchmarks. We recently introduced Cowbell Insights for them to benefit immediately from risk reduction recommendations specific to identified security weaknesses. All data is updated continuously, maintaining an always-on view of the organization’s cyber risk.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Prior to becoming a licensed producer in California in May 2019, I must have met approximately 150 insurance executives during my time in Des Moines. I thought most meetings went well. As I was studying for the producer’s exam, I became familiar with the nomenclature and the knowledge. I realized how many opportunities I missed to make those conversations productive. I wish I could have all those meetings all over again.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

I have a few of them. I enjoy decade long mentorship with George Fischer (currently President at Verizon Business), Carl Eschenbaugh (currently General Partner at Sequoia Capital) and Michael Christenson (currently President and COO at New Relic). We don’t speak often but when we do it’s meaningful and I always learn a lot. They have never given me wrong advice and always have my best interest in mind. George taught me how to build relationships in 5 minutes and still to this date when I stumble upon a problem I still think: how would George solve it?

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Innovation always comes with some form of disruption to established ways of doing business. It [disruption] has to bring significant benefits to drive positive change for all stakeholders and not just in the short-term. Cowbell’s approach closes the insurability gaps and enables all businesses to get access to better, more relevant cyber coverage based on an accurate, data-driven assessment of threats and risk exposure.

A “not so positive” approach would be to try to digitize cyber insurance by moving online the interaction between carriers and policyholders without paying attention to the network of distributors who have trusted relationships with policyholders for other lines of commercial insurance.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

Resilience and grit are two qualities critical to building a business from a ground-up. On the startup journey, you will meet more people who will offer a multitude of reasons why your endeavors will fail than people who will support you. Use your own filter not theirs to decide what path to take, and build a community of advisors around you that brings a balanced view over what you’re trying to achieve with advice to overcome roadblocks.

Lead generation is one of the most important aspects of any business. Can you share some of the strategies you use to generate good, qualified leads?

The insurance market is fragmented and regulated at the state level. Building trust at the local level and within the multi-level network of distribution channels is making a difference for Cowbell. You can’t build trust with a big-budget focused on advertising and digital marketing. I am grateful to have a go-to-market team that pays genuine attention to every person they touch in the sales cycle. As a result, word of mouth has worked well for as Cowbell is an organization that people want to work with.

We are sure you aren’t done. How are you going to shake things up next?

Because the threat landscape is always evolving, we know that we will always have to adapt and adjust our cyber insurance product and stay on top of emerging risks. This is why, from the get-go, we have built a framework that enables us to adjust rapidly how we assess, select and price cyber risks on a continuous basis. This is the foundation of our continuous underwriting platform. With this in place, we can confidently start thinking about new types of coverage and new ways to deliver cyber policies that accurately reflect how organizations deploy technology and handle security and privacy.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

I love reading (well listening on Audible) and listening to podcasts in general. I have many favorites but some of my all-time favorite books are Principles by Ray Dalio, Hard Thing about Hard Things by Ben Horowitz, Talking to Strangers by Malcom Gladwell and Never Eat Alone by Keith Ferrazzi. I love listening to Stay Tuned with Preet by Preet Bharara. I like uphill battles, complex problems, building relationships, and am a student of emotional intelligence.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Someone used to tell me often — Efforts are appreciated but Results are required. I am a “Jack get it done” guy. I believe in execution in details at the same time in self-awareness and self-management. Throughout my career I have looked up to the wisdom from the great Muhammed Ali — “It isn’t the mountains ahead to climb that wear you out; it’s the pebble in your shoe.” That is my Life lesson quote.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

There are 250 million+ kids who can’t read this article. Imagine what it would be like if you couldn’t read. Now imagine what it would be like if you can help someone learn how to read.

How can our readers follow you online?

Readers can follow my LinkedIn personal account to access all the latest podcasts and conferences that I participate in. Following Cowbell Cyber is also a great option to get a view into how the Cowbell’s team is helping shape the emerging cyber insurance market.

This was very inspiring. Thank you so much for joining us!

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Cliff Berg: “Stay current in things”

by Charlie Katz
Community//

“Simplicity is the new competitive advantage; Simplicity trumps complexity every time” with Penny Bauder & Jill Allison

by Penny Bauder, Founder of Green Kid Crafts
Community//

Heroes Among Us: “Get your team involved as much as possible” with Liron Barak and Marco Derhy

by Marco Derhy

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

- MARCUS AURELIUS

We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.