Stories From The First Ten - Year 3

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 third, you can read the first here and second 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.

Culture Eats Strategy for Breakfast, Lunch and Dinner

I’ll never forget a dinner I attended in Toronto one night with “the Great One,” Wayne Gretzky.?

Culture of Winning

Towards the end of the dinner, someone asked him how he created a ‘culture of winning’ when he won all those Stanley Cups in Edmonton.

In a very polished way, Gretzky didn’t immediately answer and he asked for the question to be repeated.? It was almost as if he was perturbed that some MBA school phrase could capture the countless hours of blood, sweat and tears that went into becoming the best in the world and winning hockey’s highest honour.? He went on to explain (sarcastically) that hockey is actually a simple game - as long as you score more goals than your goalie lets in, you win the game. And when you win, you feel pretty good.

When you win, you want to do everything possible, every minute of the day, each and every day, to win again.? Winning begets winning. He spoke about how winning, with your ultimate focus on the Stanley Cup, was all that mattered, and that drove everything - how they practiced, how they communicated, and how they related on and off the ice.? It became an obsession.

Later that night at the bar, I walked up to him and he was incredulous that anyone could believe that they read some book on corporate culture and that led to their success.? Many years later, at a rink in Las Vegas, he said to me, “Serbinis! Are you here to play or to win? There’s a difference.”

It’s the entirety of all your behaviors - how you do things as individuals and more importantly, as a team, that is the scaffolding that forms your culture.? Intentionally investing time to building your culture, nurturing it, adjusting or correcting it, and growing it is an activity that I’ve seen pay massive dividends.

While establishing your values is a year one exercise, building your culture is an ongoing one. Your culture can be a secret weapon, and as a leader, you need to invest time in it - every day.? One of League’s core values of “In it to Win it” intertwined our culture and winning from the get-go.?

Back in college I had the opportunity to work at Microsoft and I got to experience the intensity of their focus on winning.? I got to see how Microsoft competed from the inside, during a time when Bill Gates was CEO, Larry Ellison was the enemy and tech was an extreme sport.

That left a lasting mark on me that I took with me to Silicon Valley in 1996, helping Kimbal and Elon Musk build a company called Zip2.? I was only there a short while but I picked up some new lessons on ‘how’ to build a company and ‘how to win’ that I took with me when I co-founded my first startup, DocSpace.? At DocSpace we built a company, but more importantly, a culture that was wired to win against all odds.? I’ve continuously rewritten and refined that playbook ever since.

For me, culture was never about a class in business school (I studied Engineering Physics).? It has always been about the “how?”? And the ‘how’ specifically is about how you compete to win on the ‘field of play’ (i.e. your market).?

Ignition

Our third year at League started with a lot of celebrating, including League’s Year-End Townhall in December 2016.? This longer-than-usual townhall meeting started as a recap of our achievements, milestones and learnings plus food and drinks.? These days, it has evolved into a sport, with every year better than the last, and with teams competing with near-broadway-level performances recapping each month, our annual song, poetry and reflections on the year that was.? This Townhall is followed by our annual holiday party where there is always a bit of singing, including Journey’s “Don’t Stop Believing” and of course, “Everlong” which has become a company theme song.

2017 was a big year of scaling, but on reflection it is a year where we invested heavily in the foundation of our culture at League.

We always start the year with our annual kickoff event, where we “ignite” the year.? You guessed it, it’s called League Ignite.? In January of 2017 we were blessed with the “flash” himself, my friend and former Sports Illustrated cover-model, four-time Olympic Gold Medalist and founder of Right to Play, Johann Olav Koss.

Johann told a great story about how he once asked his speed skating coach what he had to do to “be the best.”? His coach said, ‘“simple, just find one thing you can help each of your teammates with.”? Johann was confused.? “How does that help me get better?”? His coach went on to explain that if he did that, and everyone on the team also did the same, he’d have six of the best young speed skaters in the world engaged with him on making him the best he could be.? This story left a mark on me, and also on League as we have built a culture with a relentless pursuit of viability, and constant adaptation to win, and achieve our mission.?

Johann got us fired up and we started the year strong.? Soon after, we heard some news that landed with a thud.? A Silicon Valley darling in our space called Zenefits admitted to some wrongdoing, laid off 450 people, and had to refactor their entire business.??

Sometimes you build your culture with examples of what’s not ok.? Most of the time, you need to invest - time and energy - and lean into things that ‘you’ or ‘the future you’ are building.? Year three was very much a year of building the scaffolding of our culture while continuing to scale up.? We invested in people, connection, and we celebrated our people, and winning together as a team.

One of my greatest joys in building companies is watching people grow to become bigger, better, more awesome versions of themselves.

We encouraged mentorship and sponsorship at League.? Earlier that year, our finance leader Danielle Cerisano, asked me to sponsor her as part of an external program focused on championing women and creating gender parity in the boardroom. We went to lunch to discuss her career aspirations and how I could help. Today, Danielle is League’s CFO,? having raised over $200M, driving a 150% compound annual growth rate (CAGR) over 8 years, and putting us on the Deloitte Fast 50, and Fast 500 lists for 5+ years running.? How’s that for growth?

First Thursdays started to get a little bigger, and more active.? Yes, we had a ping pong table, and while that alone is not the ‘culture’, the time spent connecting with each other and celebrating our wins absolutely was.

We invested in our team’s health, aligned with our mission, values and our business. ? We did classes together that were almost always health related.? And almost always competitive.

We rode together to raise money for cancer research.? We connected with the community to support many, many health causes. We had some fun and competed to win on the sand. We celebrated Pride in June. And as any good group of Canadians, we played some hockey.

The Gong: We celebrated every win by striking the gong - Go Liam! Wins of course showed up in my weekly memo to the company (“TWA” - The Week Ahead.) ? And they absolutely showed up at Townhall.?

Townhall & Culture Cards: Every Thursday at 4pm, since the beginning, we’ve shared updates, celebrated wins and reviewed learnings, and recognize each other with “Culture Cards.”? These are Leaguer-awarded, aligned to achievements that exemplified and reinforced our values.? We do these every Thursday to this very day, and we are constantly striving to improve how we do Townhall.

Power-Up: While Ignite happens in January, and Townhalls happen weekly, we decided that we needed a mid-year immersive event to refocus the team.? We celebrated our performance mid year and had a party (of course).? This is now called League Power-Up.? That particular year (2017) was special, as we rented some buses and I hosted our entire team at the lake.? Despite near gale-force winds, we achieved our goals and have been perfecting how we do Power-Up ever since.

Expansion Into the US

Meanwhile, the business was scaling nicely.? Every month ended with signing “the biggest deal ever” with Peel Elementary Teachers Local, which brought 7K teachers on to the platform.? Ecommerce leader Shopify brought thousands too, across the US, Canada and UK.?

We formally setup shop in Chicago, home of the American Medical Association (AMA), and a number of large healthcare and insurance organizations.? At first we rented some desks at at WeWork. Then a small room. Then a very large room.? Launching an office in a whole other place is a significant challenge, and for me, that challenge starts with culture.? We moved some intrepid Leaguers to Chicago to bring a seed of our culture to the US.? We did our best to connect that office to Toronto HQ and to our ‘how’ each and every week.

We continued to meet HR leaders wherever they were.? We were out in the field, learning everyday, and sharing those learnings with each other on Slack and Confluence, our ‘enterprise’ tools.?

We got invited to US Healthcare’s most important, invite-only event in Laguna Beach, Health Evolution Summit. That was both exciting, and sort of terrifying. Speeches at CES to audience of 5K to massage days at small businesses to hobnobbing with the CEOs of healthcare’s leading companies.? I was a fish out of water, but I defaulted to telling our story - origin, vision, mission, values - and I learned a ton.

We put ourselves out there, and told our story, as much as humanly possible.? Some of these moments were absolute duds.? I often say that there are only two states for a founder/entrepreneur: Zero and Hero. Most of the time, you are a Zero, trying not to wallow in disappointment or get discouraged, constantly looking to the future, and striving for better.?

From SMBs to the Mid-Market

As we scaled up, we also invested in our platform and thought of how we could best serve larger companies.? We continued to expand our platform, launching a new Health Concierge capability, while adding over 40 insurance carriers to League by August of 2017. This was important as our deal sizes continued on a doubling path and we were winning our first national and multinational mandates.?

While we had figured out how to win with SMBs, there was a lot to like about the mid-market from a scaling, economics, and mission standpoint.? We rapidly abandoned or deprioritized sub-segments of the market that we deemed to be less attractive than where we were headed. See the part about “Mountains, Hills and Valleys” in the first part of this series. This optimization behaviour continues?to this day.??

The Hard Things

Our culture and our company were both scaling nicely which is hard to do at the best of times. That October, we went through a very, very hard thing.? It was possibly the first major test of our mettle, the first test of our culture.? It was certainly a test for me as a co-founder, and as a CEO.

Our dear friend and co-founder Todd Humphrey was moving out of his day-to-day role at League.? Todd is just an awesome human being and I love him dearly.? He and I met many years ago and he was instrumental with our success at Kobo and at League.? More than driving growth, he was at the heart of the culture we were building.?

Todd lived in Seattle, and with a family so very important to him, it was not a good time for the excessive travel he was doing.? Meanwhile, the business was changing and it just demanded more of us all the time.? We worked together and made the very best of a tough situation.? Todd was a real pro throughout this period.? I am not going to lie, this personally felt devastating. There is a reason most companies do not survive losing a co-founder.? And this case was particularly hard as we’d been in the trenches together, we were friends, and we were family.?

At Townhall that week, we told the team and it was tough, but also in a way, beautiful.? Todd shared his story, but ultimately put his focus on the team and the opportunity in front of us.? “It’s a privilege to be here, at League on this mission together.? There’s a ton of people who’d kill to be here.? So remember that on your next day, next week, month and challenge.? We have and continue to build a great team who believes in our mission, and who wants to create something great.? So... be excellent, work together as a team to make extraordinary things happen.? Oh, and don’t kill the [...] cactus.”??

Todd remains a shareholder, regular speaker, and supporter of all things League.? At League Connect 2024, Todd sat on a panel alongside the former CEO of One Medical, and the VP Innovation of Disney to talk about how he is innovating in CX in the NHL as the Seattle Kraken’s Digital Innovation & Fan Experience lead.? He stole the show!

Don’t Kill the Cactus

The cactus was a lovely (and large) succulent that had been gifted to League.? It sat in the office, and we took turns caring for it.? In some ways, it became a living breathing symbol of what we were building and what was special about us: our culture.

Our third year was about investing in our culture, while still growing the company at an impressive rate.? Some of our most important scaffolding was put up and remains until this day.? And it wasn’t all parties and ping pong, it was sponsorship, health-oriented causes and partnerships, kickoffs, Townhalls and the OODA loop (Observe, Orient, Decide and Act)- a decision making framework used by fighter jet pilots, adapted to startups.

You may think that we spent a lot of time on ‘culture’ and not on the business.? Quite the contrary.? Time spent on building our culture energized, fueled, and catalyzed the business.??

I believe culture is more important than any plan or strategy. ?My feeling, a play on Peter Drucker’s famous quote, is that “culture eats strategy for breakfast, lunch and dinner.”?

It was our culture that ultimately defined us and how we competed in the market.? How we played? to win.? How we would get back up when we were knocked down.? Those words left a mark on me.? Todd knew that we had built something special? and the really special part of it was not initiative #22 on our strategic plan, the business model of the day, or a new feature we just launched - it was the team, who was in it, and how that team worked together to compete to win in this brand new market we were going after.??

I am proud to say, that many years later…. the cactus is alive and well. We have been actively investing in our culture ever since.

Keep following along and check out the recap of year 4.?