10 Questions with Jon Kessler, CEO of HealthEquity

Jon Kessler has served as HealthEquity President and Chief Executive Officer since February 2014 and as a director since March 2009. From March 2009 through January 2014, he served as our Executive Chairman. Prior to joining HealthEquity, Mr. Kessler founded WageWorks, Inc., a provider of tax-advantaged programs for consumer-centric health, commuter and other employee spending account benefits, serving as Chief Executive Officer of that company from 2000 to 2004, Executive Chairman in 2005, and Chief Executive Officer from 2006 to 2007. Prior to founding WageWorks, Inc., Mr. Kessler was a benefits taxation specialist at Arthur Andersen, LLP and, prior to that, he was a senior economist in Washington, D.C., specializing in employee benefits and environmental taxation during the Clinton and Bush (Sr.) administrations. Mr. Kessler also currently serves as a trustee of the Employee Benefits Research Institute and a director of the International Baccalaureate Organization, both nonprofit organizations. Mr. Kessler holds a B.A. from George Washington University in International Affairs and an M.P.P. from Harvard University's John F. Kennedy School of Government.

Q: If you could wave a magic wand to change one thing in healthcare in the US, what would it be?

Modesty. Too many of us are certain we know how to “fix” healthcare, or how not to. There are good ideas from all angles for improving accessibility, quality, cost, and value to the consumer.  Oh, and world peace.  

Q: Imagine 2030, what’s the average deductible for employer-sponsored insurance?

Average deductibles doubled in the 2010s, and there is no reason to believe they won’t rise another 50% in the 2020s1. But that’s not the whole story. Copays rose just as rapidly, and often do not count against the deductible. Family plans introduced embedded per person deductibles. Networks narrowed. These changes have happened because, 1) giving financial impact to consumer decisions works2; consumers spend less and pay attention, resulting in better outcomes, and (2) consumers want, and employers want to offer, low premiums.  

Consumers need true advocates in this system. The traditional players in the healthcare system aren’t incented or equipped to be those advocates3. That’s the need we aim to fill.


Q: What are your thoughts on Individual Coverage Health Reimbursement Arrangements (ICHRAs) and defined contribution healthcare in general?

We have defined-contribution (DC): it’s called Medicare Advantage (MA)4. Whether MA is “more efficient” than fee-for-service (FFS) Medicare is above my pay grade, but consumers dig the competition. So, at least from a consumer value perspective, DC has legs. However, employer-sponsored group coverage has proven incredibly durable because of its tax advantages – which ICHRAs are too narrow to change–and because non-group markets remain unpredictable year-to-year. Change those things and employers will gladly adopt DC.

Q: What healthcare startup niches are you most excited about?

I’m excited to see the opportunities for startups that emerge from the massively altered regulatory and market environment for remote medicine and from the implementation of HHS price transparency and interoperability rules. The incoming administration would do well to stick with these good ideas – even if they don’t like the source. We’ll see.

Q: What health insurance advice do you give friends and family?

ALWAYS choose an HSA-eligible plan. Open an HSA and run every dollar of your out-of-pocket healthcare expenses, including over-the-counter expenses, through it. That will save you money on both premiums and taxes. Don’t worry about how much, just figure it’s $1,000 and put that into HSA investments. It’ll pay your Medicare premiums in retirement or COBRA in a pinch. As to which HSA plan, if you have the option of a hospital system-sponsored plan like Intermountain’s SelectHealth or Kaiser, choose their HSA plan. Your next best bet is a not-for-profit locally managed BCBS plan. If you see a low deductible, low premium plan, IT’S A TRAP!

Q: Dogs or Cats?

Dogs. You know why your cat doesn’t care when you come home, or when you leave? Because it doesn’t love you. Get over yourself.  

Q: Do you have any obscure productivity hacks?

No voicemail. Nowhere. If it’s important, send me an email5.

Q: How much time do you spending thinking about the yield curve?

A flat yield curve6 is a powerful incentive to optimize every aspect of our business for the benefit of our members, teammates, and shareholders. That’s what I think about.

Q: What would HealthEquity’s culture be like without the inspiration of The Purple Cow7?

We’d find a purple moose. I think there’s a sculpture of one in Toronto, which, oddly enough, is where Seth Godin found the purple cow. Are Canadian jokes still ok?

Q: Work from home is a stock. Are you long, short, or neutral on the growth of it over the next 5 years?

Well, right now it has 100% market share, so where’s the growth going to come from? More seriously, there is no going back to mandatory full-time office work for many positionsOur biggest cities will be fine, but with remote work, get ready for a rural/exurban boom (fueled, serendipitously, by the aforementioned flat yield curve). Companies, like all social organizations, will have to work differently to build and maintain culture and cohesion. Sheet cake in the break room won’t cut it, even if it has purple frosting.

Edited for clarity. Emphasis and footnotes are mine. Disclosures: my personal healthcare coverage is a $5,000 deductible cost-sharing plan (non-ACA compliant). Healthcare investments: Cigna, Fitbit (pending deal close by Google), IPOC (Clover Health SPAC), HealthEquity.

Photo by Anastasia Shelepova on Unsplash


  1. a 50% increase over 10 yrs is approximately 4%/yr or double general inflation
  2. skin in the game
  3. for example, medical loss ratio rules mean the path to higher profits is higher claims
  4. Medicare Advantage is a value-based private alternative to traditional Medicare and it comes with out-of-pocket caps; 1/3 of seniors enroll in an MA plan
  5. I can attest to this. I've gotten to know Jon through some great email exchanges
  6. the yield curve measures the interest rates of bonds of differing maturities
  7. Seth Godin wrote about called The Purple Cow, which advocates for remarkable products that spread via word of mouth vs. traditional advertising
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