Flying high and the importance of changing engines mid-flight

Flight was always something I marvelled at as a kid. Sitting on a plane as it soared through the clouds certainly felt like it’s own type of magic. Even today, with millions of air miles and a pretty solid understanding of the physics behind it, I still find flight fascinating.  

But taking flight has also become a somewhat tired business analogy for growth and success. However, there’s one key difference when it comes to “flying” a startup that makes it much more exciting. We don’t get to land.

At League there will never be a good time for us to take a pit stop, refuel, perform a bit of maintenance, and then maybe ask some management consultants to help us chart our next course.

We have to make all our adjustments in the air – which is significantly trickier. Once I did see them try to refuel Air Force One as it was flying. But that was a movie and it still almost sent Harrison Ford tumbling out the back of the plane. So yeah, it’s tough.  

I can completely understand why watching from your seat as mechanics straddle the wings installing bigger and better engines mid-flight would be pretty terrifying for most people. But that’s the life in a startup, and at League we thrive on it.  In my view, it’s part of what separates companies that succeed from those that crash and burn.

While raising money obviously provides us with the fuel we need – I like to think of “changing the engines” as an analogy for the necessary structural changes we need to make as our strategy evolves.

These structural changes tend to materialize as reorganizations of our teams, leadership changes, and new processes. Personally, I’m finding these changes extremely exciting because I can already see the potential they’re creating.

We’re also seeing an influx of new talent as we continue hiring across the board – especially in areas like our Customer Success team. Interested in jumping on board mid-flight? You can check out our job postings here.

Flight status update

These days League needs to fly with the speed and agility of a fighter jet, which is super exciting. Here are a few things that have me really excited about League right now:

Moving up market: This has been an organizational focus for a while, but now we’re really starting to reap the rewards. Currently the size of our average new customer opportunity is 10-20x larger than it was this time last year.

Major brands: Our pipeline is filling with larger accounts and we’re starting to win them. In addition to top brands like Unilever and Shopify, it’s also great to see organizations like L’Occitane, Uber, and WE deciding that League is the right choice for their employees.

Member engagement. Unlike classic insurance, League members are on the platform every month: This gets even more exciting when you dive into the frequency. Our biggest cohort is visiting 5+ times per month. Why? Beyond the League digital wallet, we offer a range of health services as a part of our experience – like Health Concierge, Marketplace and Rewards.

Our new Health Rewards incentive program has become a major driver, with 80% of members coming daily to complete a library of 21 day programs. That’s amazing. What’s even better is that we are embarking on a machine learning strategy to leverage our growing data-set to help members with their health and benefits.  

US expansion: Our US pipeline is now surpassing our Canadian business, which is unbelievable given our time-in in the market. We’re continuing to hire in our Chicago HQ, and we’re also setting up regional hubs in San Francisco and New York. Plus, we’re now licensed to do business in nearly every US state.

With that in mind, if you’re in going to be in Chicago for the SHRM18 Annual Conference make sure you stop by to chat with us. We might even be able to get you an invite to our exclusive Cubs viewing party at the famous Wrigley Rooftops. Should be a great game.

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