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Meet the Collective: Kwesi Leggett, Engineering Manager

Kwesi Leggett is an Engineering Manager at Collective Health and based in our Chicago office. He talks about what drew him to the company.


Meet the Collective is our series highlighting the great people who make up Collective Health. Today, we’re sitting down with Kwesi Leggett who is an Engineering Manager based in our Chicago Office.

Where are you from?
I grew up in Evanston, IL but currently live in Chicago. I’ve also lived in San Francisco as well as New York.

What happened in your career that led you to Collective Health?
I was drawn to Collective Health for a number of reasons, but what really sealed the deal for me was the opportunity to open a new office. I was actually the first engineer they hired in the Chicago office. I’ve been a small company guy my whole life but that idea of being able to build something beyond the code — build the office, culture, and a way of doing things — that really appealed to me. Plus, having a say in who you work with is a unique and appealing opportunity.

What excites you most about where Collective Health is going?
The sheer amount of opportunity we have as an organization. Fixing US healthcare from the inside out is difficult, but that’s a good thing. It’s what makes the work interesting. If the problem was an easy one to solve then I think it would be far less fulfilling. There’s so much potential in terms where we can be as an organization and as a country when it comes to how our healthcare system works. And, I think it is also very reasonable to think we can get there. I can clearly see our path, and it’s just a matter of having the time. This is also the first job I’ve had where I can say “I am helping people, I’m doing good.” It’s always been rewarding to know that my work ultimately benefits the health and well-being of individuals.

What’s one of the most important lessons you’ve learned in your career?
You have to be your own fiercest advocate. If you don’t believe in yourself, and you can’t articulate why you’re good, why should anyone else? You need to have the confidence to advocate for and stand up for yourself. There will be times when it seems like nobody else will be willing to do that and you have to be that person for yourself. I’ve always been willing to bet on myself when given the opportunity. I know that doing so pushes me to be better. It instills confidence in others that I am committed and willing to step outside my comfort zone. If you know how to do everything your job requires of you then you’re limiting your capacity to grow.

What’s your favorite thing to do when you’re not at work?
Obviously the pandemic has changed things for most people but pre-pandemic, I loved going out to restaurants with my wife and friends — socializing is a big part of my life. Traveling has also always been a passion of mine. Now? I’ll be honest, I’m finding more joy in the simple things that help get me and my family through the pandemic. I have two small kids and they certainly take up most of my time, and the pandemic has allowed me to spend more time with them. Truthfully, I think the pandemic has also made me a better parent.

As a kid, what did you want to be when you grew up? How does that inform what you do today?
I wanted to be a football player when I was really little. I never really had a specific — “who I want to be” vision for myself. I’ve always liked math and I figured I’d do something with numbers. Stanford killed that dream quite quickly (my abilities stop at the theoretical). So, I kind of fell into computers — taking one class at a time, and before I knew it I was an engineer. And I’ve always wanted to solve problems so that led me to the type of work I’m doing at Collective Health.

What makes CH engineering unique?
Everyone is really helpful — that was one of the things that struck me when I started here. Regardless of which office someone is from or if you’ve ever met them in person, I’ve always been impressed by how willing people are to jump in and help with a problem. I’ve worked at other places where you have one or two people like that. But at Collective Health, everyone is like that. It creates a really cool culture.

How would you say technology can work better in healthcare?
I’d say one of the biggest things technology can do is eliminate some of the red tape. Right now there’s so much of it — and given all the silos that exist, it’s pretty common that the left hand doesn’t know what the right is doing. Technology gives us the ability to unify processes.

For example, say you go to the doctor and they tell you need an MRI. You have to find a facility to schedule an appointment. But before you can do that, you may have to call your insurance to get pre-authorization. But your insurance tells you to call your primary doctor to get a particular form filled out, and then fax it back. You then have to call your insurance back, get the finalized authorization, and then send that over to the MRI facility to finalize your appointment. And hopefully, no one messed anything up along the way that would make you have to start all over again.

The unfortunate circumstance is that the consumer, or the patient in this case, becomes the glue between siloed organizations. It places a substantial burden on the consumer to navigate a process which they know very little about. In reality, a well-built program could be doing all of this in the background in a fraction of the time. A program should bridge the gaps for you to make your life easier.

Other industries benefit from innovation and experimentation at a faster rate than healthcare because in our case, misinterpretation or experimentation can be costly. But we also have to find a better way to make technology work seamlessly in the background so that patients don’t give up trying to navigate their own care.

What’s your favorite quote?
“The capacity to learn is a gift; the ability to learn is a skill; the willingness to learn is a choice.”

Hidden talents or lack of talents?
I was a photographer in high school and college. I don’t get to use it much anymore but the skills are still there. When I lived in New York I got into boxing — I never stepped into the ring but I like everything about the sport from the training to sparring.

What drew you to CH leadership?
For me it has a lot to do with the leadership we have in the Chicago office because I work with them more closely. They abide by the philosophy of finding really smart, capable people, putting them in place, and then letting them do their thing. They don’t micromanage and they give you as much as you can handle. Some managers and leaders like to hoard their power, but that’s never been something I’ve experienced at Collective Health. If there’s something you want to do and the leadership can make that happen — they will. That’s how I got into management — I made it clear that’s what I wanted to work toward and they helped me get there. Being empowered by your leaders is so valuable.

Fun fact about me:
The street I lived on in Brooklyn was the same street Biggie grew up on. It’s now a much nicer neighborhood than when he lived there.

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