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Four Leadership Lessons From A CFO Turned CMO Turned CEO


John is the co-founder and CEO of Pie Insurance. He’s been responsible for overseeing all aspects of Pie since it was founded in May 2017.

What do a CFO, CMO and CEO have in common? They share more than a C-level title and a seat at the executive table. Each role is uniquely important to a company’s success and should never work in isolation—companies benefit from leaders who are aligned on vision and deeply understand one another’s mindsets. 

I’ve had the privilege of being a CFO and CMO, and now I serve as CEO of Pie Insurance. These are roles that, on paper, have very different responsibilities and qualifications. Yet I wouldn’t be as effective as a CEO without my experiences running the financial and marketing functions of a business.

Here are several important lessons that have stayed with me throughout my career in the C-suite.

1. Embrace scary opportunities.

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Don’t run the other way when a scary opportunity is presented to you. It may be the start of an exciting future or an opportunity to learn a valuable lesson. Frightening opportunities go beyond the cliché of “take risks!” Risks can be big or small, but the intimidating ones can seem a little crazy when you’re first faced with them.

My scary opportunity came when I was the CFO of Esurance. I loved my job in the company’s financial hub. We were in a period of exciting growth as an early-day insurtech (we didn’t call it an insurtech back then), and I was focused on building a financially strong business. 

In 2003, we were looking to hire our first chief marketing officer, and I was on the hiring committee. We were having trouble finding the right candidate, and one day our CEO took me aside and asked me if I wanted the job. He thought my leadership style and analytical mindset might be exactly what we needed. The CFO of Esurance as its CMO? Was he crazy? I didn’t have any advertising experience. I was the numbers guy. 

The sane answer—which would have also been the easy one—was to say no, let’s keep interviewing. But I knew opportunities like this didn’t come along every day. Ultimately, this became a pivotal moment in my career. I ended up serving as Esurance’s CMO for 10 years, helping to grow premium volume from $50 million in 2003 to $1.3 billion in 2013. 

Ever since then, I look out for scary opportunities and present them to my own team. This perspective has led to big goals, even bigger ideas and a team culture that isn’t afraid to try new things.

2. Adopt a growth mindset.

The term “growth mindset” has become a buzzword within organizations, but when applied correctly, it can be transformational. To me, a growth mindset means you have an insatiable hunger for learning. I’ve had this sponge-like mentality since I was a child, and it’s come in handy as I’ve transitioned among very different C-level roles.

Having a growth mindset means you aren’t limited to the confines of your title. It means you’re constantly exploring new ideas and new ways of working. From the outside, I held very different functional roles at Esurance. Being a CFO allowed me to bring an analytical mindset to being the CMO and ask questions in a way that wasn’t traditional in a marketing sense. Being a CMO allowed me to get closer to the customer and to think constantly about their journey, which has proven invaluable to me as CEO at Pie.

When I made the switch from CFO to CMO, I had a lot to learn. I made plenty of mistakes, which I turned into knowledge. Whether you’re starting your first job or are on your way to retirement, there should be no end to applying a growth mindset.

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3. Build with balance.

Originally, my career trajectory took place within financial management and traditional insurance companies. These industries historically attract the same profile of employee. We came from the same schools, with similar resumes and skill sets. For better or worse, that hiring profile has worked for these industries for decades. 

When I joined Esurance, we were a startup that brought together employees from all walks of life. Insurance industry legends and engineering geniuses found themselves at the same table. We moved fast and were never short on creative ideas in an industry that was historically fine with the status quo.

The magic that happens when you combine different areas of expertise and experience under one roof has stuck with me. Whether it’s at a team level or at the corporate level, building with balance will ensure that you constantly have different perspectives. No team, no disruptive business, should look the same. Seek out people with diverse backgrounds who are excited to work together to solve problems and execute on your vision.

4. Maintain a clarity of vision.

Too often we see companies grow at a jaw-dropping pace and then burn out. Growth for growth’s sake is not a viable business model in the absence of other important metrics. Growth without a clear vision of the destination can be problematic.

Whether you’re the CFO or CEO, you need to constantly keep the company’s vision at the forefront of everything you do. From there, you can define the levers and drivers of your growth. Sometimes you may need to make changes, pivot or even scale back in order to secure long-term and sustainable growth.

Ensure that every single employee knows what they’re working toward. Communicate with transparency about how you expect to get there and, most importantly, how your company and every decision you make impacts the customer. 

My journey as a CEO began in 2017 when I founded Pie Insurance. But the skills that help me succeed in this role today were gained over the years through key lessons I learned as a CFO and a CMO. These varied roles gave me the opportunity to learn, and now I apply that knowledge daily.

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