Advice for Aspiring Leaders in Insurtech

Starting a company has been likened to jumping off a cliff and building an airplane as you fall through the air. Risky stuff. I mean, really risky stuff. Living in Silicon Valley and around people who do this all the time as though it were normal, you can begin to think it is. Or maybe my brain has always been wired that way. At least four times now, I have boldly proclaimed to my wife of 21 years, “I have this idea, and I am going to do X.” And “Oh, by the way, we probably won’t be getting paid for a couple of years. And…well, there’s a high degree of risk involved, which means it is highly likely we won’t get paid...at...all.” In starting our current company, Limelight Health, four of us had an idea, iterated, worked hard and took no salary for over two years. We now now employ 120 people all over the globe and have raised roughly $44 million in venture capital. The journey from a chief executive of four founders haggling over how to get started and what to do, to CEO of a venture-backed company with lots of employees, has been nothing short of amazing. It has required me to do one thing, placing it above all else: exercise the willingness to let go of who I am and embrace constant change. Not in a theoretical way, but in a real, difficult, deep down-in-the-gut and character-changing, emotionally taxing way. At any company, you have to spend a lot of time talking about values. Who are you as a company? How are you going to treat employees, each other, customers and partners? It’s fun to talk about, yet much more difficult to execute. To that end, the best advice for an aspiring leader in the insurtech space would be to fearlessly create and live by tenable, actionable values. Talk about them with new recruits, talk about them in interviews, talk about them in All Hands meetings. Be sure to recognize employees who espouse them and call each other out when you’re not living up to the values. Below are some values that hold strong when leading a new company in this industry. See also: Key Difference in Leaders vs. Managers   Humility and Awareness. Leading a startup, it's easy to think you are right or that your way is the best way. Typically, leaders don’t enjoy being wrong. It’s easy to become angry when someone doesn’t behave in a way that is consistent with your view of how the work environment should be. You want to surround yourself with people and direct reports who will point out problems. When you are challenged and coached, you become humbled. From there, you can grow. All that is required is the humility to listen and the awareness that sometimes things need to change to set the tone for and build a great culture. If you aspire to lead in the insurtech space, find some humility. One way or another, when you innovate and disrupt, humility will meet you at your doorstep. Kaizen. A Japanese word for “continual improvement,” kaizen refers in business to activities that continually improve all functions and involve all employees from the CEO to the “assembly line workers.” Sometimes you have to climb into a cocoon, die and come out something altogether different. When you make a mistake, it’s important to jointly work hard to focus not on blame or how badly someone performed, rather, conduct a retrospective to discover how you can improve. If you are aspiring to lead, you have to do just that, and I can guarantee that you will be the one who changes more than anyone else. Grit. “Grit is passion and perseverance for long-term and meaningful goals. It is the ability to persist in something you feel passionate about and persevere when you face obstacles.” You will invariably face obstacles: Everything will take longer, cost more and be more difficult than you can possibly imagine. Simply put, you will need some grit to push through. See also: Setting Goals for Analytics Leaders   It is an incredibly exciting time to be in the insurtech space. There are innumerable problems, but with those problems come rich opportunities.