• The Sharing Collective

One of Chicago's Most Influential Tech CEOs, Amanda Lannert, Building a Thriving Culture

In the competitive tech world, the industry is filled with creative thinking visionaries. But what has set Jellyvision apart and earned them several tech industry awards and titles including, Chicago's 'Most Innovative' and 'Fastest-Growing,' is Amanda Lannert. Amanda leads with authenticity, genuinely values her team, and is driven by the mission, 'to be helpful.'

Amanda Lannert, CEO Jellyvision

Amanda Lannert, Jellyvision CEO, Hyde Park Angel Investor, Mentor.


She was sitting casually on a chair, wearing jeans, a t-shirt, and a blazer; Amanda Lannert, one of Chicago's most successful tech CEOs, was speaking to a group of young, impressionable girls at an event for Yea! Chicago, Young Entrepreneur Academy.


It was like sitting with a friend, listening to her share her story and experiences, but in this case, it was a rockstar (female) tech CEO. I was struck by her kindness and authenticity and inspired by her brilliance and what she has built.


Amanda is the CEO of Jellyvision, one of Chicago's fastest-growing tech startup companies, and has been the key figure in driving the company since its founding in 2001.


Jellyvision makes "software that's based on behavioral science, built on powerful tech, and somehow comes out feeling like a conversation with your smartest, funniest friend," and it's called ALEX.


ALEX is software that helps employees navigate benefits choices and makes "learning and decision making delightful." ALEX is used by more than 1,500 companies, with more than 18 million employees in total.


But Jellyvision didn't start out as a tech company. Amanda joined Jellyvision in 2000 when they were a computer game developer responsible for the popular computer quiz game, "You Don't Know Jack."


But almost immediately, Amanda saw how the gaming industry was changing and becoming gaming-console and web-based. So in 2001, she pivoted, restructured the company, and started creating software that took the interactive gaming fun that they were known for, but combined it with a serious (and laborious) subject, health care benefits, and created the award-winning, ALEX.


To say that Amanda is a force is an understatement. In addition to being a successful CEO and entrepreneur, she is a mom of teenage girls, a mentor, serves on multiple boards, and is an angel investor through Hyde Park Angels, an early-stage investors group supporting emerging entrepreneurs.



How has business been this last year, and what have you learned?


The past year has been, obviously, challenging and unusual. I say that from a place of extreme gratitude and fortune because to answer your question, our business itself has been good. Not great, but good. And that's not been the case for many companies, including many of Jellyvision's customers.


We've got the kind of people at Jellyvision who really step up during challenging times. We've been able to help our customers weather their own COVID-related challenges by first being good listeners. And delivering new products, sharing ideas and best practices from other customers with them, work with them as partners, and keep it both real and light when we can. I'm proud we've been able to be as helpful to as many customers as we have.

What have I learned? That we're all in the healthcare business. It became suddenly glaringly apparent, as millions of Americans almost overnight were faced with the possibility of becoming very, very sick, just how heavily we rely on our employers to help us stay healthy without going broke.


Jellyvision is consistently ranked as the Best Place to Work as well as one of the 'Coolest'. You've been recognized as having created one of the Best Cultures. What does Culture mean to you?

To me, Culture is not an idea or an ethos. Culture is behavior. It is what you do, what you don't do, what you celebrate, what you don't tolerate, how decisions get made, who has a voice and who has a vote – all of those kinds of things about how business gets done.

It's also something you can't fully control or dictate. It's more like a brand or a reputation than a policy, you know? You can aspire to a certain kind of Culture--open, honest, inclusive, hard-working, authentic. But the most you can do is create the conditions that allow such a culture to grow and flourish.


"To me, Culture is not an idea or an ethos. Culture is behavior".

Being in the highly competitive tech industry, how do you lead with authenticity and create a culture that inspires?

Being authentic boils down to having the ability to listen very closely to yourself and call bullshit (sorry). And, with practice, you learn to call bullshit BEFORE you say a thing out loud or send it in an email or see it show up in an interview you gave. Is this true? Do I believe this? This seems like the obvious or right thing to say in this circumstance, but is it true? How's it going to feel, like literally in my body, after I say this thing? Did I assume good intent in others? And is it actually helpful to the recipient?


I still work on this daily, and I rely on my peers and colleagues and husband and daughters, two of whom are teenagers and oh-so-willing, to help me with.


Beyond that, leading with authenticity has to do with a) doing what you say you are going to do; b) being honest, because it turns out people have very excellent built-in BS-detectors; and c). checking your ego at the door as best you can.


For example, when COVID hit, and the implications for our business were very uncertain, there were zero points in me trying to sugar-coat it. I said, Wow, this is going to be really hard, and I don't know what's going to happen, and your guess is as good as mine.

BUT...to the second half of your question about inspiration, you have to follow that kind of truth with as much honest, non-BS positivity you can muster up in your heart. It's going to be really hard, and the future is uncertain, BUT here's how I think we're going to get out of this mess. It's going to be scary, BUT we have talented people, and we are up for the challenge, and we have been through hard times before, as a company and as individuals.


"Being authentic boils down to having the ability to listen very closely to yourself and call bullshit".

What advice do you have for someone in the early stages of starting a company?

Know your customers better than they know themselves and have a plan for making repeatable revenue.


Also, surround yourself with people who will tell you the truth and have great senses of humor. (The humor thing doesn't lead to business success, but it for sure makes for a more pleasant workday).



What trends you seeing now?

I'm very interested in virtual preventive care and virtual care innovations in general--which have obviously taken off hugely during the pandemic.


In a way, the pandemic has been a sort of forcing mechanism to confront a few of the very broken pieces of our healthcare system. Like, why did it take a horrible crisis for us to make it 1000% simpler to talk to a doctor? The technology has existed for a while.

The increased focus on mental health has been intense and, I think, overdue as well, and that's a trend I'm very interested in.


As awful as this year has been, even those of us fortunate enough to have remained physically healthy have perhaps had some challenges sleeping, staying focused, preventing burnout, feeling a sense of purpose and connection. We're talking more about mental health, which is a good thing, and are also more likely to consider our employer as having a fundamental role to play in it.

What's the most valuable lesson you've learned as an entrepreneur?


It's important to have audacious dreams. The worst part of making small plans is you may actually achieve them, and where's the fun in that?


"It's important to have audacious dreams. The worst part of making small plans is you may actually achieve them, and where's the fun in that?"

What advice would you give to women when it comes to finding a mentor and building relationships?

Here is some advice I would give to women or men: First, instead of asking what you can get from a mentor, think of what you can give/add to the conversation.


Second, people want to be helpful, but you have to make it easy by having specific asks and knowing what you want.


Finally, start now. Find peers in your field and set up meet-ups, rotating who pays and whose professional obstacles you tackle.


Who or what has been your biggest inspiration?


I don't have a single iconic hero or source of inspiration. Instead, I get my verve from microdoses throughout the day, whether from my family, friends, colleagues, or a great article or Twitter thread (and yes, I can find inspiration on Twitter).



What has been your biggest challenge?


When attempts for Jellyvision to live up to our potential don't go to plan.



You are constantly growing; where do you go to learn?

  • To Amazon, where I buy and read more than 50 books a year.

  • To Harvard Business School, where I spend a week a year with other CEOs through a YPO program.

  • To multiple blogs and newsletters.

  • To coffees and dinners with my peers and friends in Chicago tech who teach me things all the time.

Is there a cause that you are passionate about that you'd like to bring awareness to?


Embarc is a 3-year program that provides community-driven, experience-based learning opportunities to low-income high school students to inspire and prepare them for college and career success.



What advice would you give your 25-year-old self?


Oh, where to start. I would say, Trust yourself.


I would say, Don't belabor the process of moving on from relationships--friends, colleagues, jobs, entire careers--that don't feel right because they're not going to get better and life is short.


I would say, Don't play Candy Crush Saga because it is time you will not get back. And I would tell little Mandy to dream big and go hard because we are all more capable and resilient than we know.

How do you balance work/life? How do you unwind?


My family keeps me grounded, of course, and an occasional outdoorsy vacation and Netflix and books keep me centered and relaxed too.


I'm in the fortunate position of being genuinely, truly intrigued by the problems we're trying to solve at Jellyvision. I am genuinely and sincerely in work-love with my colleagues, so my very happy and authentic answer to your question is: my work suits me, and I don't very often feel an urge to counterbalance it.


Who are the Five people- living or dead- you would invite to your dream dinner party?


First of all, I would want them to be living during this dinner party. I want to make that very clear:) But here's my list:

Chris Rock

Gertrude Stein

Scott Galloway

Oscar Wilde

Malcolm Gladwell


What is your motto?


Oof. I don't really have a motto, so I'll repeat Jellyvision's stated purpose because it's meaningful to me and, I think, really matters: Be Helpful.