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Past, Present, Future: League at 5

November 12th marks League’s 5-year anniversary. 

Back then, we were just four people in a MaRS office with a passion to transform healthcare, with a codename inspired by the Foo Fighters. On Nov 12 we told the world we were launching League to transform healthcare, with a name referencing ancient Roman times, and something that everyone could do each day to live healthier – walk for an hour. Today, League boasts over 250 employees throughout Toronto, Chicago, New York, San Francisco and Manila, and is revolutionizing the health & benefits landscape. To celebrate this tremendous journey, I wanted to take a moment to reflect on how far we’ve come, thank some people who have been instrumental to our growth, and shed some light on where we are headed.

League 5 Years

A lot can change in five years. In 2014, Ryan Gosling wouldn’t eat his cereal, Transformers was dominating the box office, and Taylor Swift was topping the charts with “Shake It Off” (OK, I guess SOME things haven’t changed). In the startup world, change happens so much faster; five years might as well be an eternity! What started as a moonshot idea to transform healthcare is now a company with over $100MM in funding that works with hundreds of customers and hundreds of thousands of members, thousands of health partners, and strategic partners like Workday and the Cleveland Clinic — and there’s even more in the works.


We realized early on that people think about healthcare through the lens of their health insurance, which is what led us to employers and the world of benefits – most people get their health insurance from their employer.  In fact, benefits are a higher priority than ever as the workforce has changed, costs have risen, and the definition of health has evolved for today’s consumer.

But traditional benefits are more like my grandparents’ cable TV, when the world wants Netflix – digital, personalized, and always-on. The personalization we’ve come to expect in every other aspect of our lives (e.g. Spotify, or even our tailored news feeds, etc.) was missing from health & benefits — and it is the key to driving better economics and a better experience. For organizations to provide this to employees, they need a way to consolidate all the elements of their health benefits offerings into one “front door to healthcare,” underpinned by data that enables a personalized, consumer-centric experience.  

We think of it as an Operating System for health — a Health OS, if you will, that brings together insurance carriers and benefits products; health programs; providers and services; and your enterprise systems. It modernizes benefits, makes it more easy to use, more accessible and affordable and helps drive better outcomes – good for both the employer, and the employee.  

Our mission is to empower people with their health everyday, to help them live happier, healthier lives. Our business led us to the enterprise and their employees are our members, but people are at the core of how we think about building our experience and platform. We’re thankful to have found some amazing, forward-thinking customers who shared our vision from the beginning and are helping us to completely reshape the delivery — and the entire concept — of benefits as we know them. To those committed early customers and friends who took a chance with us — thank you for believing in us.  

Creating something out of nothing, and building an organization like ours is a team sport. You cannot do it alone. It takes countless hours, evenings, nights and weekends, and it takes so many special people. “Come join me to create a new company, with no name, with no money, no product, or customers, yet – just a vision, a mission, and the will to create something great. Trust me, it’s going to be awesome.” Thank you to all the Leaguers today, and those that have helped along the way. We would not be here without all of you. I am especially proud to call so many of you my friends, that have helped create the company and culture that we hold so dear.    

To my co-founders, Dan Leibu, Dan Galperin and Todd Humphrey. Successful founding teams are super rare, and multi-company successes are even more rare. “The Dorsey File” and other one-pagers hold the initial words we shared to describe what we could build. On day one, we talked about a vision and mission. On day two, we talked about the how that would define our culture, which we all knew would be more powerful than any one strategy we could pursue.  Soon after, we sat at the Acropolis, and decided to jump into this new venture together. On Nov 12, 2014, we told the world about League. Everything since has been up and down, but mostly up and we have always had the clarity of purpose and values that you gave us, at our core. Thank you all, thank you to the Dan’s that keep powering League day to day, and to DL, who I met through a classified ad, 22 years ago, for sticking with me all these years. There’s not too many stories like ours, and that’s part of what makes League special.  

Building a breakthrough enterprise takes capital. And investors are leary of the healthcare market due to challenging complexities, regulation and long investment horizons. Thank you to our investors and professional partners for your time, your investment, and most importantly your belief and trust in us.    

Last but not least, to our family and friends: THANK YOU.  My wife and daughters motivate me everyday. I often give credit to my daughter, who suggested that it might be time to stop hanging around the house, and ‘invent something new.’ Thank you to all of our friends for your support, and your energy when we’ve needed it. And thank you to those friends like Ken Nickerson, Mike Lazaridis and Commander Chris Hadfield that have inspired us to reach for the stars.

So what does the future hold? I have conviction — more than that, religion — that every company will run an Enterprise Health OS in the next decade. We are focused on building that leading platform that helps companies transform to meet the needs of a changing market landscape, to stay competitive, with a focus on the experience and health of their employees. Data and machine learning enable greater personalization, and with that, comes the kind of experience we once envisioned, where League helps you with your health, everyday.  As organizations change, and nature of work changes too, we are reaching and empowering an ever-widening population of people through enterprises, and new kinds of partners.  

Beyond companies, of course, governments, and other kinds of institutions will need to do more to move the needle on healthcare. New market entrants will also seek to make an impact. They will all need a Health OS, and we are happy to work with them. We will continue to expand our reach to include millions of active members, and we will also drive to create greater impact with technology and with leading health partners globally.  

Looking back on my notes when we first started League, I found this line I wrote down to myself: ”There are few things like the experience of diving into something entirely uncertain, attempting to envision the future, and giving birth to a new concept, that with force of will, you make real.”  I’ve always believed that will is critical to making lasting change. To paraphrase Theodore Roosevelt, it’s not about the critic, but about the people in the arena, daring greatly, so that their place shall never be with those cold and timid souls who know neither victory nor defeat.  

For now, we are in the thick of open enrollment season at League and have new customers launching daily. We are in the arena, daring as greatly as we ever have. Five years have gone by in a blink, and I cannot thank Leaguers, our customers and investors, and all of our partners, friends and family enough with this one blog post. What I do know is this — the sky’s the limit for us and I can’t wait to write to you all on our 10 year anniversary. 

“If everything could ever feel this real forever…If anything could ever be this good again.”

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