Remarkable leadership: 10 questions with Jon Kessler, CEO Skip to content

Remarkable leadership: 10 questions with Jon Kessler, CEO

Get to know Jon Kessler, President and CEO of HealthEquity

To tell people about the top leader at HealthEquity is to tell the story of being Purple with a very intentional capital P. To be Purple is to be passionate every day about being remarkable for clients, partners, members, and teammates. Jon always tries to be forthright and approachable. With a wry sense of humor, Jon walks the Purple walk.

Jon has a long career with benefits designed to support American workers and families. He has served as HealthEquity President and CEO since 2014 and Executive Chairman from 2009 to 2014. Prior to joining HealthEquity, Jon founded WageWorks, Inc. (“WageWorks”), a provider of tax-advantaged consumer-directed benefits (CDB) account administration, in 2000. HealthEquity acquired WageWorks in 2019.

Beyond the timeline of his career, there’s a lot more to learn about Jon’s personality and background.


Dedicated to helping Americans save

Jon has a master’s degree in Public Policy from Harvard’s John F. Kennedy School of Government and a bachelor’s degree from George Washington University in Washington, DC. He also holds a US patent for inventions covering methods for electronically adjudicating pre-tax healthcare and other expense transactions. And, in 2021 Glassdoor named him a Top CEO in the Glassdoor Employees’ Choice Award with a 94% approval rating from teammates. What’s interesting about Jon is he would much rather talk about the power of Health Savings Accounts (HSAs) to build meaningful savings or how much he values teammates for the daily contributions they make in helping people understand their benefits.

Because Jon is an energetic, cut-to-the-chase type of leader, let’s get into the 10 questions.


10 questions with Jon Kessler


1. What was your first job and what is your role now?

In junior high I worked at a personal computer store and at Häagen-Dazs. Everyone asks, so I can tell you my favorite ice cream flavor is Chunky Monkey. That said, at the Louisville Bats stadium they have a dark raspberry chocolate chip ice cream that’s very tasty—plus, it’s a super purple color. Of course, neither of those flavors are part of the Häagen-Dazs lineup, but I have the freedom now to sample lots of different ice cream brands. 

Now, I’m the President and CEO of HealthEquity.  


2. What is your guiding principle or North Star?

Humility and candor.

3. HealthEquity has a strong commitment to deliver a remarkable experience. How are we continuing to improve in this area?

We strive every day for remarkable service—that wow moment that every client, partner, and member should have when working with us. I have to say, we have some work to do before we’re consistently remarkable. I know this because we’re always asking for feedback on how we’re doing. It’s so important.

So, from metrics we track and from what our members, clients, partners, and fellow team members tell us, we have some room to improve. Honestly, I think that’s a good thing. As long as we keep feeling the impact of the feedback—good and bad—in our gut and continue to act on it, we'll keep improving. And we will get to that remarkable-every-time service we work toward in every interaction.


4. What advice do you have for people just starting out in their career?

Well, my guiding principles are humility and candor, and they haven’t steered me wrong. Part of that is being grateful every day. In his autobiographical song "Mother Blues", country songwriter Ray Wylie Hubbard has a great closing line: "The days that I keep my gratitude higher than my expectations...Ah! Well, I have really good days."


5. What would surprise people to know about you?

I don't always make New Year's resolutions, but when I do, I keep them. In the past, my resolutions have included giving up sugary sodas, milk, biting my nails, and speeding tickets (laughs). If I can't think of a resolution that's worth keeping, I don't do one. The only resolution I’ve made that didn't stick is when I resolved to go to sleep before midnight. Perhaps I'll try that one again someday. 


6. What is a defining moment in your life?

I'd like to think my life is only about halfway over. You don't name the game's MVP at halftime!


7. What book influenced you in your professional life?

Like Eli Rosner, I’m a fan of the Jim Collins book, "Good to Great." And I enjoyed reading another of Jim Collins’ books, "Built to Last." I also highly recommend "Garfield at Large."


8. What cause is closest to your heart?

Maybe it’s the time I spent in the DC area for college and when I worked as an economist, but education and voting are my top issues. The health of our society depends on these.


9. What's your favorite part of helping clients and members reach their goals?

One great thing about our business is the alignment between our teammates, our clients, and our members. When members use HSAs and CDBs to their fullest, they win, pure and simple. When they win, so do our clients, partners, and yes, even Team Purple.


10. What absolutely excites you right now about HealthEquity?

My immediate thought is that it’s exciting to work at HealthEquity because we truly value helping people grow their careers. I often think about all the team members past and present who have advanced their careers as part of HealthEquity—whether it was through internal growth or by moving into roles in other organizations. Sometimes they go and come back!

To see people learning and growing here is remarkable. And I think there's much, much more we can do to help our teammates develop, but there's also a lot to be proud of. If you’re reading this, I invite you to join us. Check out our open positions and think about making your career here. We’d love for you to be part of our Purple culture.



HealthEquity: Jon, thank you for sharing your journey. Your down-to-earth style is refreshing, and your sense of humor will keep us all laughing.


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