CEO Interview: Shawn Jenkins, Benefitfocus, Part 1

Shawn Jenkins runs Benefitfocus, a leading provider of cloud-based benefits management software. In this two-part interview, he spoke with me about his journey as a CEO. In this part, he discusses how he became a CEO via a nontraditional route and developed his approach to the job. In part two, he explains how he persevered to take Benefitfocus public in 2013. He also has some insight for CEOs into the current quagmire of benefits.

Benefitfocus CEO Shawn Jenkins

Benefitfocus CEO Shawn Jenkins

What did you think you wanted to be when you finished school?

Shawn: I always knew growing up that I wanted to have my own business, and then I wanted to be able to fly my own airplane. I loved airplanes. I actually graduated with an aviation set of certificates and became a commercial pilot and flight instructor. I had some business schooling as well. I didn’t know what type of business I wanted to run but I did not want to be a pilot for a career. I simply love to fly. I felt like if I did well in business that I could pursue aviation on a personal level.

How did you get your formative business experience?

Shawn: Like many business folks I went through a series of trial and error. For my first job out of college I went to work for a nonprofit organization. It was a mission group that sent medical teams into third world countries. We’d organize doctors, nurses and supplies and set up temporary clinics. I was able to coordinate teams and do a good bit of travel myself. For four or five years I really learned a lot about people and fundraising, motivation, service and servant leadership. I watched firsthand how successful people like physicians and business people could use their careers for good to help people in difficult situations around the world. That early experience, although not traditional business, formed in my mind a view of what a business could be and how it could be used for a platform for good. This includes building great products and great wealth creation for all associates and providing for their families. Even more, it’s how businesses can have a social mission.

That was a very nontraditional route to being a CEO. What advice do you have for people who take that route?

Shawn: The advice I give people now out of school is if you can take even six months or a year, go and serve people. It gives you a good grounding of how the world really works and what opportunities are out there to not only use our careers for personal advancement but also to help other people.

As I wrapped up my job at the nonprofit organization, I still had the idea of wanting to have a business. I went through a series of self-taught sales trainings, and I purposely set aside two years to look for sales jobs. I wanted to figure out how to sell by immersing myself in a sales role. I also knew it would help me find out how to hire people who could sell if I had a business someday.

So you developed a functional expertise in sales?

Shawn: Yes, and in the process I discovered my business passion, which is software development and design. I met my partner Mason Holland, and we eventually started Benefitfocus through that work. Success is a combination of learning and getting experience but then also meeting the right people. Forming the right friendships and early business partnerships is critical. I certainly wouldn’t be where I am today without them.

Were there one or two who were particularly influential in your business thinking?

Shawn: The nonprofit I worked for really shaped how I think about creating cultures. At Benefitfocus we put a lot of focus on culture and values. We publish books on it and have a whole series on training. My early experience in helping people be successful as well as this idea of servant leadership really was profound. It stuck with me through software engineering and sales and through my journey of starting companies and growing businesses. That was very fundamental and remains a key part of what our company has become.

You’ve mentioned the idea of servant leadership. New CEOs are often surprised that they don’t have quite as much power as they anticipated. I often say you can only fire people once and it usually doesn’t solve the problem you have. How do you explain that to CEOs?

Shawn: I often quote Zig Ziglar: “You will get all you want in life, if you help enough other people get what they want.” As a CEO we’re in the business of helping people get what they want. At Benefitfocus we have a great culture and are attracting a lot of talented people on a national scale. We’re saying, “Come be part of a team where you can be successful. You can use our company as a platform for good and to achieve your own personal goals.” We say to our software designers and engineers: create great products that make our customers successful. Help them achieve their goals and in so doing, we help more people become successful, then our company becomes wildly successful. Ultimately that helps me be a successful CEO.

Check back next week for part two of this interview!

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