Tag Archives: humility

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.

Best Insurance? A Leadership Pipeline

Insurance leaders, you spend every day helping customers plan for the future, and you know that disaster can strike anyone, anytime.

But have you done all you can to prepare your company for what the future holds? Whatever lines of insurance you sell, there’s just one policy for company longevity: a strong leadership pipeline.

Unfortunately, many insurance companies forgo this essential coverage. Last year, Deloitte found that just one in three insurance companies believes its future leaders are prepared to respond to tomorrow’s business challenges — despite 87% citing leadership development as a priority.

What’s so important about leadership development? For one, leadership quality cuts straight to the bottom line. Equity analysts place, on average, a 16% premium on company stock prices when they see effective leadership. But when they perceive a company’s leadership is ineffective, analysts discount the company’s stock price by about 20%.

Strong leaders build value because they know people are an insurer’s greatest asset. They recognize that empowering team members pays off in loyalty, reduced turnover and enhanced customer service.

I’ve seen my company through nearly a quarter of its centennial life, and through the course of my career I’ve learned a thing or two about insurance leadership.

Like many of us — be honest — I didn’t grow up dreaming of a lifetime in insurance. California Casualty was my first job out of college, though, and it’s been the incredible career I never expected. The company’s mix of challenge, inspiration and flexibility has helped me grow from sales consultant to team manager to vice president.

But I’d have never reached the position I’m in — not to mention stayed for two decades — had I, too, not learned from strong leaders. Now it’s my turn to find the company’s up-and-coming leaders, and I look for five traits in tomorrow’s standard-bearers.

See also: The Insurance Renaissance, Part 4

First and foremost, effective leaders have integrity. Integrity is difficult for some, but it’s actually a simple concept: People with integrity do the right thing even — and especially — when no one is watching. In our industry, policyholders depend on us to fulfill our obligations, often when they’re most vulnerable.

That’s why California Casualty created a written code in 1965 to act as the company’s moral compass. It champions integrity and the singular importance of doing the right thing for our customers. The code reminds me — and future leaders — that it’s better to fall short of our goals than to meet them through dishonesty.

Strong leaders must also be able to influence others, and I’ve seen firsthand the importance of inspiring, motivational leadership. Before any sweeping change, my company informs key influencers and involves them prior to the full-staff rollout. This creates buy-in and helps them serve as role models to team members who might not feel as comfortable with changes, and provides hands-on leadership experience before they truly take charge.

Confidence, tempered by humility, is another quality I’ve found is essential for insurance leaders. These leaders surround themselves with team members whom they can learn from — and whom they can teach — when exploring issues and making tough decisions.

Confidence also means being transparent with your team. I don’t always make the right decision, but I’m confident that, if I make a wrong move, my team and I will work together to adjust, learn and improve.

Alongside confidence, I look for flexibility balanced with accountability, which helps to unlock a team’s potential. When I first became a team manager, I learned that my sales strategy didn’t necessarily work for others. I had to step back and recognize that there’s more than one way to exceed targets.

There’s one final trait all successful insurance leaders share: strong communication skills. To build a successful team, you must clearly articulate goals and the drivers behind them. At our sales rallies, we talk about targets, of course, but we also seek to understand the “why” behind our numbers.

We recently implemented underwriting changes, for example, that made it more difficult for sales consultants to sell policies. Taking time to discuss policies’ loss ratios and profitability issues has helped our sales team adapt to these changes and improve the company’s future.

See also: Can Insurance Innovate?  

With all the important qualities an insurance leader must possess, it’s tough to find tomorrow’s perfect leadership team. But once you’ve identified promising candidates, you’ll need to help them rise to the challenge.

First, start with face time. Get to know tomorrow’s leaders on a personal and professional level. To help them define what they want to achieve — both in their current role and in the next — work with them to create short-term and long-term goals. Boredom lurks behind turnover, so setting “stretch” goals is a great way to keep up-and-coming leaders engaged.

Second, find opportunities to let them shine. Never underestimate delegation as a leadership-building tool. When employees are given ownership, it builds their confidence, showcases their talents to others and prepares them for their next positions. I give young leaders opportunities to assist with recruiting and hiring, mentoring new associates, and leading annual meetings.

Next, give them a say in company decisions. Employees at all levels have fresh ideas that can benefit the company. By giving them a say, you nurture growth, learn their thought processes and cultivate buy-in at the same time.

Finally, build bench strength. Don’t wait for a position to open. Employ an approach of continuous development to ensure you can tap the right talent when you need it. Plan ahead as you hire: Employees who understand technology and analytics will be increasingly important for insurance leadership.

In the end, insurance leadership isn’t about titles, nor is it about sales figures. In our industry, it’s our job to be there in policyholders’ times of need; we have the chance to truly improve lives. So while I may not have always dreamed of an insurance career, it has been an incredibly fulfilling one. Now it’s my job to find new leaders who feel that way, too.