Katelyn Gleason

Allow time for ideas to come to fruition. Talk them out with others to formulate. Some ideas take years to come to reality, and that’s okay!


Katelyn Gleason is the CEO and Founder of Eligible, the leading billing infrastructure company for healthcare in the U.S. Eligible provides a software service that allows providers to automatically determine patients’ insurance coverage.

Eligible graduated from Y Combinator in 2012 before joining the Rock Health accelerator the following year. To date, Eligible has raised over $25 million in venture funding from the world’s top investors, including YCombinator. As described in Inc.’s 20 Female Entrepreneurs Everyone Can Learn From, Katelyn heads a company that has, “quietly but wildly successfully closed the gap between customer and insurance companies. If you haven’t heard of it, you will soon.”

Katelyn was recently selected for Crain’s 40 Under 40 Class of 2017. Katelyn has also been featured in Forbes’ 30 Under 30 in Healthcare, Fast Company’s Most Creative People in Business, and was named one of 17 Female Health IT Company CEOs to Know by Becker’s IT & CIO Review.

Katelyn was also invited to share her expertise at two major conferences, Techonomy Health and Fortune Brainstorm Health. She was also a guest speaker at the 2016 Cleveland Clinic Medical Innovation Summit and Y Combinator’s Female Founders Conference 2016.

Where did the idea for Eligible come from?

The idea for the Eligible API came from an epidemic we’ve seen where patients are often hit with surprise medical bills weeks or even months after they receive a medical service. This contributes to a lack of transparency and trust between patients and providers, and between patients and insurance providers. Eligible automates this entire process through an API so doctors can tell patients exactly how much they owe in terms of copays, deductibles, and coinsurance, often before they even set foot in the doctor’s office, so they don’t get a bill later.

We also saw a need in the market for providers. On average, 50% of provider revenue is not collected properly upfront at the time of service. Right now, a provider’s go-to standard operating procedure when this happens is to send collection notices to the patient. By doing that, it creates a horrible experience for the patient and it only gets them to about 60% -70% of the overall revenue collections they’re due. Providers wind up with massive bad debt and write-offs. This is money out the window for them! To address this, Eligible enables providers to deliver a better patient experience and also enables them to get closer to that 90% -95% collection rate that they deserve, because it’s money that they’re owed! Doctors work hard and deserve every penny of revenue for what they do.

What does your typical day look like and how do you make it productive?

My typical day begins with me waking up at 5:30 a.m. I then take a minute while still in bed and briefly think about the day. By 6:30 a.m., I am out the door walking over to Blue Bottle Coffee, where I get my coffee and go on a two-mile walk. While walking, I carry a little notebook in my back pocket and make note of the things that I need to address with my team that day in one-on-one meetings or all-hands meetings and I’m running with my team. Whatever I’m doing for the day, I write it in my little notebook while walking. Before that, I’ll take all of my notes that are in my little notepad and I put them in my master notebook. Only then am I able to really start my day and be productive, because it grounds me and keeps me centered. After that, I start working, and I typically have my first meeting at 9:00 a.m.

After that, I am working with my team. The former CEO of Uber, Travis Kalanick, called himself the chief problem solver and said he loved doing it because he got to work with really smart people on solving company problems that arise, and that’s how I feel. I collaborate with thought leaders in my company all day long on what we need to do and how we need to improve or set our team up for success. I go over any gaps or challenges they have to make sure we’re meeting them and focusing on executing on our vision. This is what I do all day, from morning until night, and I don’t usually stop.

To keep me productive and focused, in between meetings with my team, I try and walk six miles a day. So I take time away to like go outside, especially if it’s nice out, and walk and then go back and work. I do this every day, Monday through Friday, even Saturday and Sundays.

How do you bring ideas to life?

I bring ideas to life by allowing a lot of time for them to happen. I wouldn’t call myself patient, but I would definitely say that I am aware that the process from a thought you see in your mind’s eye to being something real, can take many, many years. This is totally okay!

How I bring ideas into reality is to allow my creative side to see it. I describe it initially to my teams as I literally ended up formulating it in my mind. It’s almost as if it’s a memory, but it’s something that I can see working in the future. That’s how I get an idea. Then, I’m very patient in the execution of it in the sense that I don’t demand myself to know exactly how it will become reality at first. I draw a really rough outline for myself usually in a notebook. Then, I collaborate with folks to bring the idea to something that’s super clear and often they will have to really push me to “cough it up” in a sense. That’s how my team and I collaborate on ideas. In my head, it’s crystal clear, and I think I’m talking about it clearly, but sometimes it takes me a long time to really get to the real idea and communicate it clearly to my team. It eventually becomes so clear when I’m talking to them, that it’s a hand to forehead moment where they are all like, why didn’t I think of that? Once it’s fully realized, fully coughed up, fully documented, written down, and everyone understands it, then it becomes real very quickly. However, in the process of formulating ideas, I’m patient with myself and the time it takes me from the moment where it crosses my mind to the time I can collaborate with my team, execute it, and bring it into reality.

What’s one trend that excites you?

One trend that excites me is in the HealthTech world and in the startup world, there are so many platforms for transparency now. People are openly discussing topics that you used to only get access to if you were friends with the right people, or if you had enough money, or if you grew up going to the best schools. Those were the only ways in the past that you would get access to certain information.

I had none of them personally. For example, I don’t party at all, neither do I drink. Growing up poor, I went to a state school and didn’t have access to any of the things I mentioned. I’m so excited about the fact that I can just go on YouTube and learn from all of these incredible people and gain access to what was never available to me before. I’m so excited about this trend. Also, it relates to healthcare, because I feel like people are starting to talk the problem that I’m solving, in preventing patients from receiving a surprise bill, in a way that was not discussed before.

What is one habit of yours that makes you more productive as an entrepreneur?

The one habit that makes me more productive as an entrepreneur would be to wake up early and get to work—it’s habitual. I like that being the first part of my day. Not because I’m an entrepreneur, but I actually enjoy it. To me, it doesn’t feel like work. It’s my daily drive that tells me to get up and get going!

What advice would you give your younger self?

Great question! The advice I’d give my younger self is, “don’t be so hard on yourself!” I would tell my younger self to not be so hard and critical on myself. Obviously, your integrity should be perfect at all times. But just for silly things I was picking on myself and feeling like an outsider. I would tell myself to stop the negative self-talk and get on with it.

Tell us something that’s true that almost nobody agrees with you on.

Something that’s true and people almost never agree with me on is that surprise medical bills are preventable! We can prevent that. People still don’t know or believe that this can happen.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

One thing I do over and over and recommend everyone else do as an entrepreneur is to walk. This for me is my therapy and my meditation! I call it like my antidepressant. I’m not myself if I’m not walking.

What is one strategy that has helped you grow your business?

Surprisingly, one strategy that has helped me grow my business was when I hit a roadblock in growth. I was new to management and feeling very uncomfortable by it. This kind of power wasn’t my strong suit. What I found that helped, and started to stimulate growth again, was to really look at management from a more empathetic and composed, structured perspective. A structure can be built, where within that structure people can kind of dance and creativity happens. When I started doing a bit of convention around how we operated as a company, that really started to spur growth from a creative perspective and then, in turn, from a revenue perspective.

What is one failure you had as an entrepreneur, and how did you overcome it?

The biggest failure I had as an entrepreneur is assuming I wasn’t being good enough, and in this, I made myself not good enough. I would want to work so hard to be a part of the Silicon Valley entrepreneurial culture and always thought they all went to universities like MIT or Stanford. They’re almost all men. I would go off on my own and work extremely hard because I felt I wasn’t good enough. What that did was actually the biggest failure, as it hindered my ability to prosper completely. It cut me off from information about how to make myself better. This was a very painful lesson to learn, but eventually, really owning the fact that I was good enough and had something to offer through my hard work really allowed me to overcome it.

What is one business idea that you’re willing to give away to our readers?

One idea business idea that I would like to offer your readers is to make a solution to automate mundane tasks that people don’t enjoy doing. I personally hate going to the DMV. I have no idea how to make it a better experience, I just know that it needs to be fixed. They should automate all of the pain away. Another thing they should automate is doing your taxes. I used TurboTax but still don’t feel like it’s doing for me what it could be doing for me. I just want to not have to worry about any of that stuff. Automation could really come in and save the day for a lot of pain points we experience in our everyday lives so we can be more productive and focus on what matters.

What is the best $100 you recently spent? What and why?

The best $100 I recently was buying Poland Springs three liter water bottles. I’ve got a bunch of those and I try to drink one of them a day. I just feel that it’s good for me.

What is one piece of software or a web service that helps you be productive?

A web service that helps me be productive is definitely Google Docs! I cannot live without it. I probably use Google Docs more than any human in the universe. I use it in landscape format, writing down everything. The reason I really like it is that when working with my team, it makes us all be so precise together because we’re looking at the same thing and discussing the same sentence. I’m obsessed with it. I use it every single day, all day long, and I could not live without it.

What is the one book that you recommend our community should read and why?

“High Output Management” by Andrew Grove, is the one book I’d recommend to the entrepreneur community.

What is your favorite quote?

“This is the true joy in life, the being used for a purpose recognized by yourself as a mighty one; the being thoroughly worn out before you are thrown on the scrap heap; the being a force of Nature instead of a feverish selfish little clod of ailments and grievances complaining that the world will not devote itself to making you happy.
I am of the opinion that my life belongs to the community, and as long as I live, it is my privilege to do for it whatever I can.
I want to be thoroughly used up when I die, for the harder I work, the more I live. Life is no ‘brief candle’ to me. It is a sort of splendid torch which I have got hold of for a moment, and I want to make it burn as brightly as possible before handing it on to the future generations.” ~ George Bernard Shaw

Key Learnings:

  • Have a morning routine that eases you into the day ahead. It’ll help you relax, map out and control whatever comes in front of you for that day.
  • Don’t be so hard on yourself! Being critical and hard on yourself will only hamper your productivity and self-confidence.
  • Allow time for ideas to come to fruition. Talk them out with others to formulate. Some ideas take years to come to reality, and that’s okay!
  • Surprise medical bills are 100% preventable!


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