Where We Are and Where We’re Going

The life of a startup is like being a X Games athlete – crazy, exhilarating, and ultimately not appreciated by many (outside of those who get ESPN 8).   

The ups are awesome, and they only encourage greater thrill seeking behavior. But the downs are often desperate. I get asked all the time, “How’s it going?” and I’ll say “Great!” because any alternative seems like it would require too much of a time commitment. After years in the arena, you learn to dampen the highs and the lows to a manageable band and focus on one thing, moving forward.  Zero, hero, repeat….but always moving forward.

In the last year, League has moved forward light years. Today I thought I would share an inside look into our last year of scaling.  

Level set

League was founded in 2014 with the vision that healthcare would be different in the future – personalized, preventative, data-driven, and always on. We set out on a mission to empower people with their health everyday, and we very quickly learned that health insurance was the lens through which many people accessed health care.  

So we dug in, and learned that health insurance is getting more expensive every year, employee needs are being met less and less, and no one loves the experience of using it. We realized that we had to re-imagine the health insurance experience to achieve our mission.  

In 2016 we raised a Series A, and launched our platform to sell health benefits to employers.  Today, League is to insurers what Instacart is to grocers. We are a digital platform that offers a new experience and a new kind of channel partner for carriers.  

We do not underwrite, or take medical risk. Instead, we focus on delivering a new experience with this idea that the future of health insurance is not about insurance, but about health. We have hundreds of employers as our customers, and we are continuing to build out our platform as we expand across the US and Canada.  

Here are some of our major advances and learnings from the last year:  

Our product

We started selling insurance as a licensed broker in a few provinces in Canada in late October 2016. We thought our MVP (minimum viable product) of one plan design, one carrier, and deep integration was the winning plan. We were wrong, and it took us a while to figure that out given the sales cycles in the business.   

Today, we have partnered with multiple carriers across the US and Canada, and we think of ourselves as being plan design agnostic with an open platform and a broad assortment of products. Like Instacart is to grocers, we deliver a new experience and a new channel to carriers. It seems simple now, but getting to this point has been a tremendous amount of work –  especially given the law of inertia.

Insurance carriers are giant companies who can simultaneously view us as either the future, insignificant, or an existential threat. One of those is true. Which one is a matter of perspective.  We continue to build out our platform with an open approach, and the great news is that carriers now come to us to partner. We look forward to working with them all.

League Partners


Determining our target customer

I somehow seem to always get this wrong in the beginning. We thought really small businesses (5-20 employees) would be the ideal target for League. That turned out not to be the case.

Micro SMBs are typically super budget conscious and often experience high rates of bankruptcy. This makes cost of acquisition and lifetime value tough metrics to manage.

But the larger the business, the bigger the health insurance headache, and the bigger the overall employee benefits challenge for their CEOs and HR leaders. That’s why we have consistently moved up market in the last 18 months. Our average is squarely in the mid-market (which we think of as 50-5000 employees).  

We have signed some amazing customers like Shopify, Tucows, and Unilever and we’re continuing to grow our relevance in this segment. These larger customers have significant employee engagement/retention challenges, massive administrative headaches, and a real desire to bend their cost curve by getting employees to proactively engage with their health.

They aren’t looking for a cut-rate deal. They want more from their broker and they want more from an employee experience standpoint. That’s where we come in.   

Here’s a great example of one of our customers:  

Several hundred customers later, we’re continuing to move up market and we’re also working with thought-leaders in industry. Increasingly we are winning customers with a national and North America-wide footprint because we can deliver a unified experience across the US and Canada.  

Refining the member experience

In our early days, League was a marketplace with a consumer experience to discover – scheduling and paying healthcare providers digitally. That was the feature. Today, the product is so much more – encompassing a member experience, admin/hr experience, and an operational platform behind them that connects to carriers and other partners.

Member satisfaction

The member experience is also a lot more than a fancy app layered on top of insurance. Judging by our engagement metrics, NPS scores, and testimonials – our members think of us as something much more. We are becoming their go-to ‘portal’ for their health.  

League's NPS score


The League app is feature rich – including a digital wallet, a health concierge, a provider network/health marketplace, health reward programs, chat-based customer care and more.

League’s Digital Wallet

Our digital wallet is now a unified place for all of your employee rewards – including insurance, health and wellness, spending accounts, charitable accounts, education accounts, and transportation accounts.  

League Digital Wallet

League’s Health Concierge

Our Health Concierge feature, which is made up of a team of health professionals, is helping scores of people with issues ranging from a simple rash on a child to more serious issues like mental health and organ transplant concerns. We have thousands upon thousands of health stories of how we’ve meaningfully moved the dial on our members’ health outcomes.  

League Health Concierge

League’s Marketplace

Our marketplace, where League all started, is now filled with a wide range of products and services that compliment our provider network. Gym memberships, food delivery services, charities, specialized health services… the list goes on. Our members are able to find providers, book appointments, and make payments all through the League platform.

League Marketplace

Excellent customer service 

We’ve all had the frustrating experience of trying to understand our health benefits coverage or to deal with a claims issue. That’s why our excellent customer care has also become a real selling feature for us.  

League Customer Care

Engaging employee wellness programs

We’re also offering new employee wellness program options like JumpStart to go with our established Health@Work offerings. Our Health Rewards beta program for employees is also showing excellent engagement numbers, so we will continue to expand our offerings to include a wide range of programs designed to help people get ahead of health issues by taking preventative measures.  

League Health Rewards

More than just an App

One of our biggest learnings has also been just how much behind-the-scenes software and servicing is required to deliver a great experience for our customers in the world of health insurance. Today League actually has much more software in the back than in the front.  

We have now built operational tools for customer care, our marketplace, our Health Concierge feature, and our administrative services. We have also built connections into leading HRIS systems. For example, now when we are doing customer launches, we will often plug into a BambooHR, Workday or other HRIS platform.

And perhaps most importantly, we have built our administration platform to be a more powerful benefits-admin tool that significantly reduces the need for laborious HR admin work.  

League Admin Experience

Boosting compliance

We are also working within a highly regulated market, which means means we have made  significant investments in regulatory controls, standard operating procedures, and compliance. This process is never ending.

We have also built out our security, privacy and compliance team and we’re now working with many leading advisors. We know that the further upmarket we go, the more we will be tested and audited. But as a result, we know our platform will continue to improve for all of our customers.  

Finding the right people

Startups need to constantly augment or up-level their people. It’s very rare that the people there at the beginning are the people that will get you to the end. So its a constant effort to build the best team, and in today’s competitive environment that means being creative.   

In the last year we have brought in some industry expertise like our President Brian Ancell, who’s run a US insurance company, and Ana Perez, who ran health marketing for one of the largest HCM advisors in North America.

We’ve also started building out a team in the US, which is one of the biggest health insurance opportunities on the planet. We chose Chicago as our HQ, and are now about to open satellite offices on both the east and west coasts of the US.  

Looking forward

Building something out of nothing is easy in the beginning, but gets hard real fast. For League, working in a highly regulated market in such an important industry has meant managing many complex challenges all at once.  

We have come a long way. Solving some real hard problems in product, sales and marketing, experience, and customer service. What’s clear is that we are now way beyond product and searching for market fit. We have hundreds of employers as our customers in a trillion dollar North American market, and we are making a real impact with our members.  

Many startups say they are disrupting X or Y. But it’s mostly just a power word that everyone likes to use but never really achieves. Disruption happens when a significant group of people change their behavior and/or when incumbents start losing business to the point where it hurts.  

That’s about where League is today. Traditional benefits brokers and the traditional experiences they provide are being disrupted by League.  

This next phase of scaling and competition can go non-linear real fast. Non-linear is where X Games athletes thrive.

If you’d like to be notified when I publish new blogs throughout the year, simply signup for the League Newsletter here.

Tell us a few things about yourself, and we'll show you how we can impact your business for the better.


Thank you!

A member of our Sales team will be in touch shortly to tell you more about the services we offer and answer any questions you may have.

Get Our Newsletter

Thank you

Ready to make
employee benefits a
whole lot easier?