The Cowbell Factors Podcast, Ep. 12: Cowbell’s secrets to success with founder and CEO, Jack Kudale

by | Mar 21, 2022 | Podcast

Cowbell is on a journey to the top. Our latest $100M funding round confirms this. Of course, our tremendous accomplishments over the last few years have been a group effort, but they truly would not have happened without Jack Kudale, Cowbell’s founder and CEO, and his secrets to success.

In last week’s episode, Jack shared his thoughts on the funding, Cowbell’s “secret sauce”, and his experience leading a young, successful company. 

Cowbell was founded in 2019, and the timing could not have been better. Cybercrime targeted towards small and mid-sized enterprises (SMEs) skyrocketed during COVID and is still at an all-time high. That is not going to change anytime soon. 

Fortunately, Cowbell’s latest funding round will enable us to do all the changes necessary to address such a shifting and quickly growing market. The funding will directly impact our three main stakeholders: brokers, policyholders, and partners. “We estimate that the cyber insurance market will be a $100 billion premium market by the end of the decade. Our latest funding gives us the opportunity to really take advantage of this intense industry growth. Firstly, we are looking to invest into our go-to-market expansion to continue to support our broker network.”

“Secondly, we will continue to invest in our closed-loop risk management, like data science, underwriting, risk engineering, and claims handling, which will directly benefit our policyholders.”

“The third area that we will invest in is our risk-bearing initiatives, like Cowbell Re, and our cybersecurity partners.”

Our close collaboration with cybersecurity vendors is another one of Cowbell’s secrets to success. 

“The cybersecurity lifecycle doesn’t end with prevention and protection, which is what cybersecurity companies have been primarily focused on. It also is not just response and recovery, which is what insurance companies have traditionally focused on. Instead, all of those steps need to be combined.”

Cowbell understood that early on and created the cybersecurity marketplace Cowbell Rx. “Cowbell Rx is essentially a prescription for our policyholders. Beyond just being able to understand their cyber risk, they get recommendations and insights on how to improve their cybersecurity as well as concrete tips on how to implement specific measures.”

It goes without saying that creating all that and more comes with a lot of work. Every day, our Cowbellers work hard to drive the innovation that Cowbell is known for at immense speed. That requires inspiration not just from each other, but also from our leader. 

“I believe that inspiration is about the transparency that you bring into the business. My philosophy is: The more transparency you bring in, the more explicit trust you get back from your employees, partners, suppliers, and policyholders.” 

He also emphasizes the importance of hiring the right people. “At Cowbell, we hire drivers, not passengers.”

Another one of Cowbell’s secrets to success is our large female workforce. About 40% of our Cowbellers are women; another unheard-of number in both the insurance and tech industry. 

“I am really proud of this, and also that Cowbell was one of the five insurance companies that got awarded the DEI award.” 

Instead of seeing diversity in his team as just another box that can be checked off now, Jack makes it obvious that this is something he is truly passionate about. 

“Even with a 40% female team, we ask ourselves, why not 50%? Why not more than 50%? I believe that we need to continue to do more.”

“The more transparency you bring in, the more explicit trust you get back from your employees, partners, suppliers, and policyholders.”

There is no doubt that Jack is very good at what he does. He advises other entrepreneurs: “Aim for solving a complex problem in a big market. In the long run, this will always pay. Secondly, build a team that compliments you. Thirdly, know that the vision that you have when you begin your journey is likely not going to stay as you bring in new players. It will have fingerprints from others, and that’s okay. Just know that, with time, everything will come back full circle.”

This has certainly worked for Cowbell in the past, and Jack already has big plans for the coming year.

“The next two years will have in store some of the most defining moments for the company. They will create and define the vision of what Cowbell will look like in the next 20 years. The Finance and Marketing infrastructure of the company will become resilient enough to withstand even the toughest market scrutiny. There will be international market expansion and new product innovation.”

If you want to learn more about Jack’s secrets to success, his approach to DEI, how he hires leadership, and how Cowbell Re helps us further penetrate the market, listen to the podcast episode.

You can also visit the Cowbell Factor Podcast library to listen to previous episodes and stay up to date on upcoming ones. It is available on most podcast platforms (Spotify, Google podcast, Apple podcast, Anchor, Breaker, and Radio Public). 


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