Leadership and the Art of the Cannonball

As a sentimentalist, I believe strongly in marking occasions, in appreciating beautiful things that you know will always have meaning and bring you back to exactly what you felt at an important moment in time. A little over a year ago, I was out to lunch near my office and I passed a gallery that had an amazing piece of art in the window.  It was titled “Cannonball”—a multimedia piece by Eric Zener that shows a diving board, a pool and the distinctive splash of someone who has just cannonballed into a pool on a spectacularly sunny day.  Like all great art, it made me feel something and although I had no wall to put it on, I decided I had to have it.  To me it channeled fun, immersion, and doing something new that holds lots of possibilities.  It wasn’t a coincidence to have that reaction, since I had just joined a team that was jumping into the creation of Berkley One, a new personal lines insurance startup.

We’ve been working hard to build the organization from the ground up, and our efforts are finally coming to life. Just last week, we opened our doors to offer home, auto, collections and liability policies in Illinois, and we expect multiple states to follow closely behind.

For the Berkley One team, this is the biggest adventure of our careers. Starting an insurance business might not be everyone’s idea of adventure, but it IS ours, because we’re passionate about making it work.  We are also passionate about the idea that we exist to help make sure clients can keep living their adventures uninterrupted.  As we have built and learned and grown over the last year, that symbolism of diving in has become more and more on point.  In fact one could say that there have been leadership lessons revealed from studying the “art” of the cannonball.


1) Athletes with an Olympic background are great, but the art of the cannonball requires technical skill plus a little something different. 


And in fact if you are too impressed with and mired in your own past, you will miss the real reason you are at a start-up, which is to create something that is of unique style and form.

When we started building the Berkley One team, we decided our #1 priority was to find people who first and foremost wanted the adventure and challenge of a startup.  This sounds simple but it wasn’t always the way that people ended up at our door.  Of course, we were looking for technical knowledge and experience, but we also made it a priority to find people with a sense of fun and the willingness to put themselves out there, without self-consciousness.  We wanted individuals who know how to solve problems because they believe there’s always another way to do things—not just one way.  After all, you have never heard of a technically perfect cannonball.  The magic of that particular dive is what the individual brings to it.

One of the interesting lessons from this experience was that, because this was our focus, we ended up with a team that had shared values, but was incredibly diverse in backgrounds, skills, and perspectives. This blend of talent gave us an amazing knowledge base, and each new team member made us better and better as a company.


2) When you aren’t encumbered by “the way things have always been done,” you’re free to make a splash with the new and the different. 


And as a new entrant you need to have some splash, otherwise you are just another version of that which has already been done.  That is neither compelling nor fun and a good cannonball should be both.

It’s an amazing time to reinvent the way insurance can work! There’s an influx of ideas and technology, and a real openness to questioning long-held beliefs. We hear it when we talk with potential clients, with agents, with business partners and within our own organization.

That hunger fueled our momentum to make a real difference with the launch of Berkley One—to go “all in” on building an insurance organization that would work better for everybody. We are part of Berkley, [one of the largest property casualty insurance providers in the U.S.], where we have the resources and autonomy to create a business without being bound by the limitations or pressures of working with legacy systems. This meant we were able to reimagine everything from mobile apps to claims procedures, making them work for the way people live today.

For us, that means combining high-touch and high-tech. While most people only engage with their insurance provider at two points—when they buy the policy and when they have a claim—we’re setting out to be a consistent presence both in person and through whatever channels clients want to use. Really it’s about being on demand for our clients in whatever way works for their life, and gets them back to their home, or on the road, or enjoying what they have worked hard for—as seamlessly as possible.


3) Even for a free form dive, you better be smart about understanding the conditions. 


Having the freedom to build requires a different kind of thoughtfulness, otherwise you run the risk of building something that doesn’t matter to your audience.

You can’t find your true “sweet spot” without understanding what your environment needs from you. So we asked around. (And around, and around.) We asked people who might become our clients. We asked independent agents who might want to work with us and who we knew we wanted to work with—in fact, we built our agency portal entirely from agent feedback.  We even visited state insurance departments in person to talk about our ideas for blending high-touch personal service with new technology.

The response, from everyone, has been gratifying. We’ve found that when approached with absolute genuineness, people want to be part of something that has been built to meet their needs with care, solid thinking and hard work.

One of the many things we did differently when talking with independent agents, in particular, was that we didn’t take any presentation decks to our meetings. Rather than marching through slides, we sat down with agents in the middle of their businesses and talked with them. It felt like we were part of their operation. Because we respected that this is their journey, as well as it is ours, the very way we interacted with them was remarkably different from what I was used to in a more traditional environment.


4) Just get in the water.  


Once you’ve prepared and gotten to the edge, the right dose of creativity will allow room for flexibility. You only improve your form by jumping in over, and over again.

The world changes fast, and it always will. So building a better insurance provider has to mean building one that will keep changing to keep moving forward with clients, agents and everyone else.  Nothing takes the place of being in market, which is why our launch is so satisfying.

The fundamentals have to be solid and durable. Everything that touches a customer has to deliver on the promise you make. But there must be enough flexibility to allow for experimentation, understanding, celebration when you get things right, and honest course-correction when you don’t. In life and in business, I’ve learned that it’s not about making the perfect dive—because sometimes fixating on the perfect can get in the way of the great. It’s more about making that big, spectacular cannonball from the painting I love so much—going all in with passion, care and the determination to amaze.

So here we are, on the diving board, making our first of many leaps into the water. And like any good cannonballer, we will continue to pay attention to the splash, work on our technique, and keep enough sheer enjoyment in the fact that others choose to be part of our adventure. After all, the true art of the cannonball is that it very often inspires everyone else to get into the pool to join in the fun. At Berkley One, we’re jumping right in.


Kathleen Tierney is President of Berkley One.