Stories From The First Ten - Year 5

Ten years ago, we embarked on a journey to transform the healthcare experience. Our mission was simple: empower people with their health every day. Today, League is a leading healthcare CX platform with 20 million users, serving some of the largest healthcare organizations in the world. This year, we'll drive over 100 million healthcare interactions, collect over 2 petabytes of health data, and drive 10X the industry average engagement. We have grown revenues by a 107% compound-annual-growth rate (CAGR) over the last 6 years and have customers all over the world.

With our 10th anniversary fast approaching I'm commemorating our journey in a 10-part series. This is the fifth, if you missed the first you can read it here. My intent is simple - share some of the learnings through our story to celebrate our team, and to inspire or help other aspiring entrepreneurs.

Note: For almost all ten years, I’ve written something each week called “TWA” or The Week Ahead, and shared it with all Leaguers - that’s nearly 500 posts! This is a great chronicle of our journey, and beyond my memory, the primary source material for these posts.

The Relentless Pursuit of Viability

Andy Grove and I first met when I was 18, on stage in Nashville, Tennessee at the International Science and Engineering Fair, or what I fondly remember as the Nerd Olympics.? I was called up on stage for the Gold Medal, or 1st in the Engineering category for my work on high temperature superconductor based propulsion systems.? Yes, I was a super nerd.? He was the CEO of Intel at the time, a company that was in hypergrowth, and driving the computer revolution alongside Microsoft.??

I went off to study Engineering Physics in college, and in the summer of my freshman year I got a job working for Microsoft, doing AI software development on a project that would solve the traveling salesman problem, applied to network routing, and this work was very close to what the Intel processors of the day could handle in terms of multithreading and parallel processing.? I got to meet Andy a couple of other times after that first time on stage in Nashville, and each time I was just in awe of the man.??

While small in stature, Andy was a giant among technology company leaders.?A Hungarian immigrant to the US, he was a powerhouse that in many ways drove the personal computing revolution.?Andy was known to be hard driving, and a student of the game when it comes to management.?Andy famously said that "Success breeds complacency.?Complacency breeds failure.? Only the paranoid survive."

Triple → Triple → Double?

Our fifth year at League (2018-2019) started with great momentum and an aspiration to double the business again after two consecutive triplings.?We had a plan. It involved moving further upmarket to the enterprise segment of the employer market.?Doubling again was going to be a real stretch, but we were compelled to achieve industry-leading growth, at all costs.??

One of the things you always think constantly about as a founder is: “Is this it? Have we figured it out? Is it clear sailing from here on out?? Can I let up?”??

Studying Grove would lead you to an easy “no.”?

Another powerhouse, my co-founder and friend of 27 years, Dan Leibu, once said that succeeding in high growth tech is a Relentless Pursuit of Viability.?It never stops, and while you should have a plan, you need to be working on the ‘next plan’ at the same time because you never know when you’ll need it.??

Every year at League starts with our annual kickoff event, now called League Ignite.? This started in the theater room at the local Soho House, and over the years the venues have expanded and contracted (COVID).?In January 2019 we were in the Bell Lightbox, the host venue for the Toronto International Film Festival.?

At the 2019 kickoff, I told a story about the importance of digital transformation in healthcare. Starting with today’s consumer, “they do not want their grand/parents cable TV”....

They want Netflix.?A user experience that was personalized, digital, and always on.?

We were convinced that there would be a pure-play in the category of healthcare digital infrastructure.?We saw a new “tech stack” emerging in the industry and we could be a critical part of that stack enabling user experiences that were more like Netflix, and less like grandma’s TV.?

In just two years of selling into employers, our average deal size had grown 48X exiting 2018.?Our closed annual recurring revenue (ARR) was up 68X.?Our largest deal was 610X bigger than our first.?Total contracted users were over 65,000, up significantly year over year.?We were absolutely ripping.?And our people were feeling it.?

And we were starting to enable real impact, which after all, was what our mission was all about.?This was just mind blowing.?We were really helping people with our technology:

Things felt good, but I was uneasy.??

Malcolm Gladwell, a New York Times bestselling author, whom I got to know during my years as Founder & CEO of Kobo, once wrote about the tipping point.?Of course, this often gets applied to business, and the dream of any founder is for you to hit that point when everything just rips and gets easier.??

Amazon had just announced a joint venture with Berkshire Hathaway and JPMorgan to tackle America’s growing healthcare challenge.?All the media pundits called the “race” as won. This threesome would dominate the market whenever they came out with their magical new service (they accomplished zero).

There were a number of companies ‘ahead of us’ in years (Castlight, Accolade, Collective Health) with very different models and they were getting a lot of attention among investors and the media. But honestly, I just didn’t get it.?They fit a pattern I had seen before: the first companies out of the gate, the look good, until they don’t. And often become footnotes in history of the category.??

The market was shifting.?Or at least that’s what I felt.?Something in the back of my mind (paranoia) told me we were doing a fine job climbing the hill but there was a different way.? We just didn’t know what it was yet.?So I did two things as CEO: I made sure we ran the play we had, and keeping Dan in the back of my mind, I was looking for the next play.? After all, only the paranoid survive.?????

Running the Play

There was of course a growing intensity and volume of activity to achieve our next double.?I hired a new Chief Commercial Officer with an incredible career in enterprise sales, selling into HR across North America.?She brought in key leaders, scaled our sales organization and set up the machine for a new stage of growth.?There are moments when it all feels right and easy, even though you are spending your brains out.?This is one of those moments.?We were building an enterprise sales machine.???

And while we were at it, we also grew our team significantly and increased our gender representation. 53% of all Leaguers, 62% of senior leadership, and 30% of Exec were women. We were inspired by the diversity of thought we were achieving and sought to actively invest in diversity and inclusion more broadly.?

On the product front, we renamed our core offering “HBX,” short for Health Benefits Experience running on our “Health/OS” technology platform.?All of our messaging, sales collateral, and sales tools went through a big update cycle.?We ramped up our HR focused events and marketing strategy, including increasing our relationships with industry analysts.?

We were in the big Leagues.?We had our first mega-wins and mega-losses.?One of those losses was with Google’s global HR team.?That was a defining moment that significantly pushed us to level up, and we did - but just not enough.?Sometimes the losses are more important than the wins, and this case was one of those times.?Google made us better, and it made us hungrier and more competitive still.?

Our business caught the attention of Workday and a budding partnership began.?We saw what we were doing as an extension of the Workday enterprise platform, the dominant enterprise system of record in the market.?We started working with Workday’s head of strategy and ventures, Leighanne Levensaler, on how 1 + 1 could equal a million.?Working with big partners can be exhausting and also a huge waste of time.?This one felt right and we pursued it.?Leighanne would go on to invest in League, and upon leaving Workday, join the League Board of Directors.???

As we moved up market, we saw the importance of relationships with system-integrators like Deloitte. They, of course, are among the biggest players when it comes to enterprise transformation, moving to the cloud, and implementing Workday.?So we became friends, drafted partnership agreements, and began teaming together in the market.??

With greater scale, we also started to see the importance of clinical information, navigation and connectivity to the US healthcare system.?We ended up partnering with one of the marquee names in the market - The Cleveland Clinic. The Cleveland Clinic became our “Chief Medical Officer” and a strategic partner as we began creating an intense health program catalog with impressive depth and breadth.?Visiting the Clinic opened my eyes to how little we knew, and just how much we needed to boost our healthcare IQ.??

While our mission is to empower people with their health everyday, we were absolutely, and still are to this day, a technology company first. This partnership was vital in boosting our sense of urgency when it came to the mission, and the people and partnerships we needed to be successful.?

Like a good tech company, we came home from that trip and ran a “health hackathon” to ideate on how we could boost the health IQ of our platform.?

All of this growth required more space. ?And we took over a space in Chicago to open our new US HQ.?The US was our primary market, and Chicago was central.?It made sense and we went for it.???

The team there was really, really great.?

We went on a hiring spree, and as a part of that, we built a strong summer student and co-op program to prime the funnel with new talent.??

And we invested in a new company-wide recognition program, called LXL - short for League of Extraordinary Leaguers.?This was a President’s Club on steroids.?Not just for sales.?Not just for extraordinary performance on KPIs or objectives. But bigger, and broader, incorporating performance and display of our values across the organization.

LXL started out as a trip, but has grown to be so much more, including providing high performance leadership coaching, advanced health benefits and compensation. ? In many ways, it’s a recognition program like no other I had built for a startup.

Sometimes in the midst of all your focus on work, life can happen.??

Well, life happened.?That year, one of our most extraordinary Leaguers faced a personal health challenge of her own.?It was devastating news for her, and for her League family.? It was a defining moment for League in many ways.?How would we handle it??I remember asking, based on our values and our mission, how should we handle this??I am proud to say that as a company, as a team and as individuals we were the best version of ourselves in that moment.?Even partners of ours like the Cleveland Clinic stood up for our Leaguer.?We raised money, extended benefits, and in many ways went above and beyond to make a difference in this Leaguer’s life.?I would not change any of that for the world.?

Throughout the year, we grew our pipeline and grew sales significantly.? We signed some great logos and we continued to scale up with enterprise deals, with innovative HR champions. Average-selling-prices (ASPs) doubled, which is saying something after our performance the prior year.?

But it was also a grind, and a lot would come down to Q4 that year. A new team, a developing enterprise playbook, many twists and turns but overall, our play was working.?

An Unexpected Round

An old friend and mentor once taught me, “when the ducks are quacking, feed them.”?When it comes to fundraising, investors can show up unexpectedly, and even though you may not need the money, it’s often best to take it.?And so we did.?Workday Ventures showed up, alongside Telus Ventures, and we did a $42M fundraising round that we called our B-2. ? There were, of course, many reasons not to do the round that we ignored.???

It might be the easiest round we’ve ever done.

The Dock

The Toronto Raptors roared to the NBA finals and won the championship that year.?I got to see some incredible games, including watching Kawhi Leonard do the unthinkable. Later that summer I met with Raptors’ General Manager Masai Ujiri and members of the Raptors ownership group, including Bell CEO, George Cope.?They told some awesome stories in risk taking and leadership about how that season came together.?

I also had some great conversations with Logan Green, CEO of Lyft at the time.?He talked about deeply complex, and hard problems in healthcare, transportation and energy. And that resonated with me.?

We were at one of my favorite “un-conferences” called The Dock, modeled after Eric Schmidt’s (former Google CEO) Curiosity Camp.?The Dock is held in Muskoka, one of the most beautiful lake districts north of Toronto, often called Toronto’s version of the Hamptons.???

I had a conversation with another attendee one night on the (actual) dock over a beer.?That conversation was an example of the kinds of conversations I was having throughout the year, in the background, in search of the “next play.”?

It started with a late afternoon question: “Could we build a healthcare experience on top of the League Platform? Why would we reinvent the wheel when you’ve already figured out so much?”??

After summer was over, we agreed to get our teams together to answer this question.? Things looked very promising and there was clearly a giant opportunity for League, and a significant win-win to achieve.?We put a SWAT team on this, separate from our core direct sales team to create some separation and minimize the distraction.??

As you might imagine, there was some debate inside League on whether this made sense.? ASPs were doubling, enterprise traction was just beginning and it looked like we were going to hit our ‘double’.?There were certainly members of the team and Board that thought this was a distraction, or worse.?This was one of the first times we ever had a significant debate at our Board.? And for good reason.?Things were going well and this was, in one respect, different.??

On the other hand, this was perhaps the much bigger, and more exciting opportunity in front of us: to power all kinds of healthcare experiences, and move from thousands or tens of thousands of users impacted, to millions or tens of millions.??

The greater opportunity was intoxicating.?I remember seeing images of dozens of apps spewing out of an iPhone, celebrating the power of iOS. And similarly, many e-commerce stores coming out of the Shopify platform. I could see how we could do the same for healthcare.

We focused a SWAT team on this project, and by December we had signed an initial agreement that we would convert into a set of master agreements early in the new year. ? What could possibly go wrong?

Only the Paranoid Survive

As the year was wrapping up, our ASPs were doubling again, users were up 3.2X, and we were maintaining very high NPS of 74 and super high engagement of 60% MAU.?Our deals were bigger, and mainly coming from the US with long 3 year+ terms.?We exceeded the ARR double we were shooting for and we had signed the biggest deal in our history.??

By most measures, we were crushing it.?

The play we were running seemed to be working very well, by all accounts.?

And believe it or not, I remained uneasy.??

League was already getting recognized in Canada by the Deloitte Fast 50 program, across the US and Canada by various awards, and we achieved our first global recognition with CB Insights Digital Health 150.?We were one of the few international winners outside the US and the only Canadian company.

Our first platform deal, launching what we would later dub?“Powered by League”,?was either a wild distraction, or the start of something spectacular.? After all, our vision was about accelerating the digital transformation of healthcare, and our mission was about empowering people with their health everyday.?The idea of powering applications - many or all the applications that mattered in healthcare was a mind-virus that was growing and in direct conflict with our core enterprise playbook.??

But it just felt right, and it connected to my sneaking suspicion that there was a bigger play for League, and a better path to achieve our mission.??

At the end of the year we thought 2020 growth would come from continued direct sales expansion, and new channel partners like Workday and Deloitte.?Which upon reflection, made a lot of sense.?Our third growth vector was a long shot that was hard to ignore due its scale, the logic supporting it, and its connection to the growing market opportunity in digital transformation in healthcare.??

Looking at our 2020 risks slide from my Board deck that fall, the risks were tied almost exclusively to achieving the next tier of growth: hiring and ramping attainment, funnel conversion, and customer success development.??

I was feeling the intensity. Recognizing what we had achieved, but was still uneasy.?We were firing on all cylinders but we had no idea what was about to hit us.?And it if it were not for that conversation on a dock, on a lake in Muskoka, Canada, and the risks we took afterwards, our future would look very different indeed.??

Thankfully, we had our next play already in motion.

Sometimes you need to capitalize on that feeling of ‘unease.’ As Andy Grove once said, only the paranoid survive.

Keep reading for the summary on year 6, the year that changed everything.