Scaling Up [S6.E2]: In a League of their Own with Mike Serbinis, CEO and Co-founder of League
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Mike has built businesses alongside Bill Gates and the Musk brothers. In this conversation, Mike shares his lessons and points-of-view on a variety of topics including the emergence of cloud marketplaces and their impact on enterprise technology deals and the deliberate and thoughtful nature of culture at League.







Ed (03:14): Mike, welcome to Scaling Up. It’s an absolute treat to have you on the show. I think a great place to start is maybe just to set the tone and give people  a quick thumbnail sketch of what has been an incredible entrepreneurial career, League is not your first rodeo. You’ve had some great experiences that have built up to this. Maybe let’s start there and hear how we got to you starting League.

Mike (03:41): Yeah, great to be with you here today. It’s been a long story; I’ll try to make it a shorter one. You know, I was the kid that grew up and all of a sudden was, you know, the math and science kid that won the Nerd Olympics. You know, I ended up true story winning this international science and engineering fair that the US Department of Defense and National Science Foundation puts on. And that got me, a gig at NASA’s Jet Propulsion Lab. So as a teenager, working on Next Gen Super conducting propulsion systems, I kind of got the bug building things was fun, you know, imagining a better way to do something, trying it out, figuring it out, building it. That was my first kind of spark of excitement around being a, an engineer, I guess is how I thought about it. Initially, that NASA gig led to working at Microsoft, and so graduating from college, great opportunity to go work at Microsoft, Big job, you know, access to Bill and Nathan.

And yet I got this call, and the call was from a guy I met in my dorm, my college residence, Big South African guy named Kimble Musk. And Kimble was like, hey, you know, my brother and I we’re building this company and we’d love, you know, you to come and help us. And I, I was like, Sounds amazing. What, you know, what’s the company? And he’s like, well, you know, we don’t really know yet. It’s going to be on the internet. And I said, Oh okay. That could be a lot of things. You know what’s, it called? Well, we don’t really have a name yet, but Global Linking Information Network is what we incorporated. Like, okay, that name sucks. But , you know, what can you pay? Like I had the six figure Microsoft research job, which in those days that was a big number.

You know, I came from pretty humble roots. My parents were immigrants to Canada, from Greece. Buying my first computer was like several months of pay from my dad. And so, the several, you know, a hundred thousand dollars job was a big deal. And yet these guys were offering something called Options and no cash. And so, believe it or not, I took the job in San Francisco or actually in Palo Alto making no money working with Kimball and his funny brother Elon. And that was my first experience building a company and not just a technology or a product. And it was a lot of fun. And I thought, wow, I really, this whole concept that people will give you money to really fund you building something that may or may not work out. So, I I got the bug and I’ve been on this awesome journey since cloud storage was next dock space.

We exited a few days before the peak of the market in the year 2000. We had no idea what any of that meant, but it was sometimes, I guess it’s better to be a bit lucky than good. And we grew the next company to, you know, reach a billion people. We were the largest consumer email platform. I moved back to Canada, launched a company that was Amazon Kindle’s biggest competitor worldwide called Kobo. We exited that to Rakuten, and then I just wanted to keep going. And so, this thought of transforming healthcare and the consumer experience and healthcare was really the next big exciting, impactful thing. And that’s when we started leak.

Ed (07:18): What an incredible snapshot. Thanks for sharing all of that. And the common thread throughout this, it feels as though you’ve attacked problems with a consumer lens right throughout your career. And I think that will become evident as to how you’ve thought about League over that journey. We’ve got a bit of an international audience and so I think it’s probably worth also just taking a moment to provide a snapshot of the US health ecosystem to which League plays in, because it is convoluted, it is complex, and for many that don’t have a day-to-day touchpoint, it can be very confusing. So maybe just as a starting point to set a baseline, a quick snapshot as you see it, of the landscape in health.

Mike (08:00): Yeah, it absolutely is very complex. And if you did not grow up in the US you would find it incredibly confusing. I think if you did grow up in the US you would find it incredibly confusing. The US is the world’s largest healthcare market. It is about 4 trillion, a year represents just under 20% of GDP. It’s an incredible complex machine. A ton of money gets spent each year. It gets more expensive each year. You know, the US is a market where people can regularly go bankrupt, having not the cash that they need to support their healthcare needs, which coming from Canada, or other markets in Europe or Australia. And that’s a very foreign thing for such a big part of the economy, something that so many people depend on and so important, it has a massive experience problem. Healthcare, NPS is, you know, low single digits.

It’s lower than what prisoners feel about prisons in America, believe it or not. That is a higher NPS score. It generally has a huge engagement problem, when it comes to people engaging with their health plan or health insurer with their provider, you know, hospital or clinic or primary care. When I ask the question to us healthcare executives, you know, talk to me about the engagement, like how often do you reach or touch or communicate with your members, patients, consumers, most people actually don’t know the answer to that question because they just don’t think about it that way.

And so, this initial idea that we had, that the mass consumerization of everything has been going on for now, you know, a decade or two, and somehow, somehow healthcare is escaped, being transformed, and this idea was it would happen. And you know, people, myself, certainly my kids, I mean, they have a very different idea about how things should work than, than I would say we have patience for. And you know, their view is healthcare should be more like Netflix and less like their grandparent’s cable, tv, personalized, digital, always on. But it’s just not that today. It’s the system that was created in a very different way, very mixed incentives and you know, it’s just untenable. It cannot sustain itself in its current format. It has to change and the consumer’s going to be in the center and that, that changes started.

Ed (10:32): A great description. And of course, there are a couple of big different stakeholders involved in this ecosystem, namely the payers or insurers as would know them here in Australia, the providers of healthcare directly and indirectly, and of course in the US employers who provide a lot of the healthcare plans as opposed to on an individual level. So just trying to set the landscape.

Maybe it’s just worth now working within this ecosystem were League fits in today. You talked about being at the center and the consumer being at the center. Traditionally there’ve been multiple touch points for the consumer within this ecosystem. If I want to go to a healthcare payer or provider, I needed to do so individually. Where League is today is providing a platform for the consumer to do this in one place. And we’ll work our way through this because it is complex, but maybe just in your own words, where League fits in today in your mind and the problem that you’re solving today.

Mike (11:29): Yeah, so I think your description of the landscape and the big actors in the landscape, is really important. Payers are your insurance companies. Providers are your hospital systems, hospitals, primary care pharmacies are a big part of the equation as well. Other consumer health organizations, employers are really where most people get their insurance from if they don’t get it from the government in the form of, you know, Medicare or Medicaid. And all of these organizations recognize their leadership, their boards, they recognize they have a serious problem, that they are not delivering an experience that the consumer loves, can engage with, wants to stick to, and it leads to all kinds of problems. Those problems really depend on where you are, but they lead to essentially bad economics and bad outcomes. Neither of those are good. So, they’re all trying to transform, they’re all trying to change their experience and in some ways they’re business models and how they engage with that end consumer.

If you’re a payer, you talk about that person as a member. If you’re a provider, you talk about that person as a patient. If you’re an employer, obviously you talk about them as an employee. And so, as they go through this process of transformation, there’s options. They could do it all themselves, building it from scratch entirely, you know, that would be close to impossible for most organizations. They certainly won’t have the capital, the time, or a time machine to make that happen. They can become an integrator or work with an integrator to assemble a litany of different point solutions to try and kind of create an experience that will work in the future. Our view is that healthcare needs infrastructure, just like eCommerce needed a Shopify like the cloud needed a Salesforce, a healthcare needs a League, a digital platform that becomes the basis that everybody builds on to quickly transform the experience for that end customer and frankly transform the business of healthcare.

Ed (13:41): I love the Shopify analogy and I think people will probably gravitate to that cause it’s easy to get your mind around this consumer centric digital front door and the analogy plays out. You have this huge legacy and large retailers who may want to in fact build their own proprietary technology stack of which the eCommerce is the front door to that. But that is a massive lift that requires not just dollar investment, but a huge amount of time and also risk. And all of a sudden to have this plug and play infrastructure layer that they can build on top of to create the output of a consumer centric app, a front door where all your touchpoints take place is really powerful. And that to me really brings what the League customer proposition is to life.

Mike (14:30): Yeah, you can think about a model where it’s a lot of broken telephone and nothing works and nobody knows who I am and I’ve got to fill stuff out again and I’m getting generic advice or I’m getting advice that I cannot afford, or I’m getting directed or not even directed to something that is just not for me and is not going to help me imagine that shifting to a model that I have one place to go that helps me access, navigate, pay for healthcare, where I have a personalized health journey that is all about keeping me healthy, happy living to be able to do all the things I want to do with, you know, myself and my family live longer and frankly afford it. Whatever the business model may be. Whether that you’re living in Canada, the US, Australia, Europe, it doesn’t matter. The economics are a part of this and an enabler, imagine that better experience that just makes it all simple where I have this one place to go.

That’s the kind of experience that League enables. The NPS score is not a seven or an eight, it’s more like a 70 or an 80. The engagement is not like once in two or three years. It’s all the time. It’s not this annoying place that you need to go to do something that never works. It’s that trusted partner in your health that just makes things happen. So that’s the kind of experience that we’re enabling, and you know, many organizations have tried to do it on their own and they’ve generally not succeeded, and they’ve spent hundreds of millions of dollars big IT departments, big contracts with global systems integrators, hundreds of point solutions, and ultimately, you know, a whole bunch of spaghetti code and you know, an experience that just didn’t work well. We have a, a way to do it that’s fast cost a fraction of what it would cost otherwise and delivers a proven experience at the end of the day.

Ed (16:29): We touched on it to start with and hopefully it’s emerging. This customer experience and centricity that is being provided around the consumerization of healthcare in this case, and I guess at the center of this as you pointed out, is engagement and driving simplicity in amongst the very convoluted, of course, this is what kickstart your flywheel in my mind, and that’s member engagement and that can provide more data, that can allow for more services and attract more payers and more insurers. Am I right in thinking about it like that? Yeah,

Mike (17:01): Absolutely. When you have the old model, which is people barely connect with you, they file a claim or they go for a procedure and that’s really about it, you know, there’s very little data that you get, there’s very little ability to personalize the experience, either to drive better health outcomes or better cost management or revenues on the other side of it, however, if you haven’t experience it captures the entire person and, you know, knows that person brings not only your medical record, but other health information your profile together to help really create a, an experience that’s personalized to you.

Well now your potential to drive not only this positive great NPS score, but to drive an experience that drives real benefit for people. And you know, the greater benefit you have for people and you know, the more that they are engaged with your brand, you know, the more that they stick generally the more that they can have better health outcomes and ultimately that just drives, frankly, competitiveness for both a payer or provider or whomever it is in the ecosystem, which frankly just makes the other players in the ecosystem want to transform faster.

And once you fall behind building it on your own over the next 10 years is not an option, right? You, you need the platform, whether it’s the Shopify of or you know, the old Intel inside analogy. Yeah, sure, you can go build a microchip on your own, but why would you do that?

Ed (18:32): It’s fair to say we have a, a pretty good picture here of League in its current form, but one of the, the lessons I’m keen to extract from you is around this idea. I’ve heard you talk about product market fit against this relentless pursuit of viability because League wasn’t always an infrastructure layer. It started off almost in a marketplace capacity and has evolved over time. But keen to understand the lessons that you’ve drawn over time to really shape the strategy of League as we see it today.

Mike (19:03): I think over, over the years of building different companies in very different industries and ultimately having very good or excellent outcomes, you have the opportunity to do the pattern recognition. And I, I feel like I’m a student of the game so I’m always trying to hone the craft, so to speak. And you know, I guess a few things that I’ve noticed, consistent vision, consistent mission is pretty vital, you know, and your vision can evolve almost like you know, a sculpture can be refined over time, your mission. And I think of that as, you know, who is your customer and what value will you bring to them. Honestly, I think that mission has to remain pretty true and pretty consistent over time, almost everything else. And I’m, I’m skipping over values, but I want to come back to that later cause that’s a whole other conversation.

But almost everything else, like the nature of the business, how your model works today, honestly, I believe is up for iteration and adaptation. And so, we always say, you know, consistent mission, relentless adaptability, you know, relentless pursuit of viability. I’m not in this to lose, I’m not in this to make something that’s not going to work because I have an old idea, frankly, that was arbitrary about what the business model should be. So yeah, we started with a marketplace type model here, but really that was testing out the consumer experience, which in many ways it’s so funny like how everything that goes around comes around. So many of these, and I’m talking about the largest brands in healthcare, they’re the leaders. They have the most capital, the most innovation dollars to spend. They have the biggest profit bulls, what they want from us is really a lot like that very first experience.

But it just had a, we had a direct-to-consumer marketplace model, which is just not the right model. We evolved that to a small business model, small business SaaS, okay? There was something there. We saw traction, we saw version of product market fit. The old mathematician slash physicist in me thinks of product market fit like a landscape, lots of hills and valleys, but ultimately only one mountain. And sometimes you could be on a hill and think you’ve arrived at the mountain, but you’re just on a hill. And so that’s the small business SaaS offering where we built an application on our platform, and we sold it as a way to centralize health and benefits and wellness for employers. That was a hill. And we migrated from that hill to a bigger hill selling to larger companies. Our average deal size went up 10 x and then another 10 x year over year.

And then we thought, wait a minute, everybody wants a version of this same thing, but they just want it in a slightly different way. This is not a product market. This is a platform market opportunity where we can provide that fundamental platform the Shopify of the SAP of and help accelerate companies. So yeah, we’ve been relentless and even today’s version of it, I’m working on the five-year version, you know, from now and how this one will evolve still, but I think the platform is here to stay. It just makes sense the in the economics of this market and how, you know, how this market needs to transform.

Ed (22:30): I think that’s a nice place to segue into other scaling challenges as it relates to what you’ve just discussed. And one that comes to mind is the go-to market, and you’ve touched on it already, but these huge deals that Leagues trying to put together around massive digital transformation for some huge businesses. We’re talking tens and hundreds of millions of dollars in many cases. We also have multiple potential customers in various channels, be it payers or providers. You’ve had already great product market fit in the insurance space and there’s appetite for other deals to be done in the other channels. How do you think about resource allocation and actually making sure that you are focused while all the more growing the business, but ensuring the core is strong?

Mike (23:20): You know, I think this is a constant problem that every founding team or every executive team, every CEO faces, how do you prioritize and allocate resources, so you get the best outcomes that you’re looking for. In our case, we saw that form of product market fit initially in the employer space, and we just followed it iterated on it to get to a better place, the best version of that. But it was still suboptimal in the platform shift. You know, when we saw payers as the natural place to focus, because they all had those employers as customers, they have them as customers and they saw what we did and they thought, we want that, but we just don’t want to build it all ourselves. We want to build on top of your platform. So, there is absolutely a lot of runway in the payer vertical. However, providers are becoming payers too, and the pharmacy or that consumer health, they’re becoming providers and some of them are also becoming payers.

So, it makes it a bit murkier, and it makes prioritizing, you know, more challenging. So, our view is we started a bit wider. We created some experiments across different segments knowing that these segments, they would transform over time. They all will, or they’ll, they’ll perish, but no one knows which ones will go first. Yeah, I’m sure there’s a McKinsey paper on this somewhere. In fact, McKinsey was here last week, they gave me the, a hundred-page slide deck. But you got to do some experimentation, you know, in your focus. I think of focus like a portfolio manager, you know, so I’m like 80% allocated to the payer segment, but I’m going to leave some room from experimentation and the provider segment, consumer health segment where we are seeing product market fit, but there’s just not many big pharmacy retailers that matter. Walgreens in the US shoppers in Canada, Walmart, and Amazon, CVS, and that’s kind of it. So, portfolio approach, got to leave some room for experimentation and you got to leave room in your process. And here we run very much a quarterly process. You got to leave room in your, in your cadence to constantly iterate.

Ed (25:56): Love that portfolio, mental model, great CEOs that we’ve seen over time are great capital allocators. And so that naturally plays into that. Of course, with the go to market, traditionally these enterprise deals, it’s not just direct, but can also be driven by the essentials and Deloittes of the world, these huge consulting firms that are paid to drive digital transformation. But one emergence that I do want to talk to is cloud marketplaces. You know, you are starting to think three to five years out and it feels as though this is where things are moving. Cloud marketplaces are an extremely fast mechanism to sell and to buy and transact. And it allows enterprises, I guess, to extract more out of these big deals that they’re doing with their cloud providers. This is probably a new idea for many listeners. Maybe can you give some colour around what these cloud marketplaces look like and how Leagues thinking about interacting with them?

Mike (26:54): Yeah, absolutely. All of the major clouds, public clouds like Google’s GCP, Amazon’s AWS, Microsoft’s Azure, they’re all assembling marketplaces. And in those marketplaces, a company like League can list its enterprise software or services in that marketplace for sale, either at a prescribed price or to some price TBD. And then ultimately the marketplace acts. It acts like an app store really for enterprise software. And just like, you know, the original Apple app store, how they would manage payments. These marketplaces like the Google marketplace, it does the same thing, collects dollars from the actual end customer and then routes dollars into our bank account. What’s interesting is how they are shaping up and why they are shaping up. And they generally have different reasons, but ultimately, if you think about it, a cloud provider is ultimately trying to amass scale. They’re trying to amass customers that will use them for storage and compute and services.

And those are all good commodities, and you know, they’re just raw resource. How do you actually get a customer to, you know, want to use more of those resources while you build great software that can consume those resources. And so, it’s not enough if you’re one of these organizations to sign a big commit to spend this money annually on compute and storage and services that commit will go away in a heartbeat if there’s no meaningful applications using or consuming those resources. So that’s where stacks like the League platform come in. We are avid users of compute and storage and services, and so we look like an interface to accelerate the adoption of the cloud for an entire industry healthcare, which is, you know, the biggest industry.

Ed (28:59): It’s crazy to even start to imagine what this can look like; enterprise deals being done in marketplaces as opposed to these long slow sales cycles. It’s mind boggling to be at the forefront of it.

Mike (29:13): You know, I’ll interject this one thought. , when we were first in our enterprise kind of phase of growth at League, I kept getting asked by all kinds of investors, board members, you know, to really refine and share, you know, what’s our, what’s our rep, you know, scaling model quota times rep times attainment equals , you know, summed over a spreadsheet equals what I can accomplish in a year. And I had this moment where I met a CEO in healthcare, seasoned individual, and I asked him, I said, you want to tell me about your rep model and how you’re scaling? And he’s like, oh, is your board telling you got to hire more reps, or you got to, you know, make your enablement you know, more efficient, effective? I’m like, Yeah, I’m hearing all this, and you know, I’ve run different go to market models over the years, many different ones, but this one was kind of new to me to be totally candid.

And so, this CEO says to me, I have only 10 reps. I’m like, how is that possible? You’ve hundreds of millions of dollars of revenue, you’ve only been around for like seven to eight years. And he is like, oh, I figured out a different model and this model is very efficient. I mean, he was talking about three to 400% efficiency sales and marketing efficiency League’s model today is about that three to 400% sales efficiency. It’s not a model that requires hundreds of reps. It’s a model that’s more of a team-based approach and it leverages partners like the global systems integrators, the cloud companies like GCP. Google is a big partner of ours. It’s a highly efficient model. And to your point, I think it’s going to get more efficient over time. Now we still got work to do, but I think these cloud marketplaces are going to play a big part of that.

Ed (31:06): The beauty of enterprise software is, is only going to get more beautiful as a, as a business model. It’s hard to imagine. The next topic I want to tackle is something that I know you are passionate about and it’s something that you’ve seen over time and, and that passion has only grown and that’s around scaling people and culture. And there’s many elements to this. And listeners of this podcast know that there’s always a good chunk of time allocated to this particular topic, be it compensation or hiring or just scaling culture and embedding mission and values and what that actually looks like.

There’s so many lessons that other business builders can take. So let try and dig into a few of these. And the one that I want to start with is probably that last one, and that is embedding values, embedding the culture as you want to see it, what that actually looks like in practice. And I know that you use culture cards at the town halls, but maybe it’s worth just shaping this up as to how League thinks about scaling culture more generally.

Mike (32:09): Yeah, so how League thinks about it is really informed by years of trying out different systems at different companies that I’ve built and, and recognizing this headline that culture is is a superpower and you can’t outsource it to anyone. It’s the CEO and founding team, exec team’s responsibility. But ultimately, you know, it has to be a big portion of the CEO’s time because it does require constant adaptation, constant growth or it goes stale and then it’s no longer a superpower for me. It starts with not the what or the why, it starts with the how, how do you want to compete? How do you want to play on the field of play? Are you going to be fast or slow? Are you going to be focused on quality? You know, that’s the Toyota way. What things will you stick to even if you get punished for them?

That’s an old Jim Collins adage, which I learned from him feels like 20 years ago. And, you know, that was for us a day one exercise in the League sort of founding story. And we came up with our version of how, and we’re very particular about what we picked because we believed those values would actually be a competitive advantage or help us shape a competitive advantage. And so, you have to think about all the kinds of ways that you can reinforce, add colour, add texture, you know, grow how you deploy and recognize people reward people and ultimately, you know, continue to develop those values. And so, you mentioned culture cards. It’s a simple expression of appreciation from one league to another in front of the entire company at our town halls, which happen every Thursday at 4:00 PM like clockwork since the very beginning of the company.

And the culture cards are, you know, token of appreciation. They usually are attached to one of the values like dream team or in it to win it. And, you know, a short anecdote that honestly that little bit of authenticity from one League to another in a small, small gift that you know, is more just token of our appreciation. It goes a long way. There’s so many other examples that are woven into the fabric of how we work every day and every week, whether it’s in Slack, which we’re big users of in our HR system, where you can reward people and recognize and give people props. In our performance system, we talk about all stars and strong performers, and you know, newly on deck Leaguers. And so yeah, it’s just a part of everything we do. And I always ask in the first month that I meet a new league, I host this like coffee with Mike. I always ask at the end of that, it’s usually an hour that it’s everybody who’s new. It’s everybody’s job to be thinking about what are new ways that we can weave into the fabric of, you know, our business ways to reinforce our culture, make it stronger.

Ed (35:23): It’s these little moments that build tradition and build legacy and it’s wonderful to hear you describe that. Thank you for sharing. One of the interesting scaling challenges that I know that you’ve had to deal with over time is the moment that the business inflects and goes from hiring generalists and people just have this ability to solve complex problems and, and drive things forward to specialists. And I imagine this is even more pertinent in healthcare where the specialization is important. Can you talk to the journey that you’ve been on and as a leader around this inflection point of moving from hiring generalists to specialists?

Mike (36:01): It’s a journey that typically happens in every company as it scales. In the beginning, you know, generalists, smart people that can solve problems and figure things out and don’t have preconceived notions and frankly have a beginner’s mind. They’re super valuable specialists too soon perhaps you can get down a path that is too close to the status quo or you know, the blinders come on, the expressions of, oh, that will, that won’t work, that will never work. You know, those things start to, I would say dampen the creative process, but eventually those generalists are not enough in this market, in healthcare. And with League I had zero prior healthcare knowledge. I just had dissatisfaction as a customer and I had it in many different ways and I experienced it with my family and with my friends, but I knew nothing like zero about the, I had never even attended like a healthcare lecture or like a talk.

So yeah, eventually you got to bring in somebody that knows something that frankly can lend credibility, can bring knowledge and experience in. The question is where do you bring that specialization in first? Because it’s possible to bring in specialist even past an inflection point that bring you to a, an old way of doing things or bringing you to a way of doing things that is just not going to work too rigid or frankly, you’re at still a stage even though you’ve passed an inflection point with a rate of change is high. And if you bring in a specialist that has had a career 20 years, 10 years, 30 years in an industry, honestly dealing with this rate of change can be frantic, can be anxiety rid can feel not in control, can feel not good. And you find, you know, the performance equation doesn’t work out.

So, figuring out where to bring the specialists in and not to overdo it when you do. So, I always like to think in terms of experiments, let’s try it out, let’s learn. Let’s see what works and what doesn’t. That’s really served us well. And you know, in League I’d say we had some misfires where we brought in specialists from, let’s say the brokerage part of the business, which is another important actor in the us even Canadian healthcare systems. What we’ve since learned is, you know, we’re selling platform infrastructure, software, and solutions, bringing in market experts that have sold technology in that have become generalists in such a way, but started as specialists in healthcare, from tech, from Salesforce, from, you know, GCP, from ServiceNow, from Accenture. You know, these are the kinds of people that can be very helpful to us right now, but it’s a constant process and I feel like I’ve made all the mistakes, right, and I never want to make them again, but inevitably you make some of them and so you just got to keep on it. It’s an important part of scaling.

Ed (39:04): One thing that it feels like you have cracked when it comes to hiring is being able to attract a great diverse workforce. And some of these statistics are incredible and really define market leadership. In my mind, 50% of your engineering leadership team is female. 40% or more of the engineering team more broadly are female. 40% of Leaguers identify as non-white and 20% identify as LGBTQ. How have you thought about diversity and to achieve this has obviously been very structured, methodical, and thoughtful, and many businesses have diversity debt and are, are trying to think about how to move to something as I’ve just described. What lessons have you learned along the way that many other business builders could maybe take out around building a diverse workforce?

Mike (39:57): You know, I, I guess I’ve had the experience over time and some great role models through those experiences that, you know, diverse teams are just, they’re better teams, they’re better at winning. And so, diversity of thought, diversity of decision-making diversity of experiences, diversity of life experiences. And when you’re building a company, especially in our case that’s trying to empower people, all people, not just some people with their health every day, equity is a real important dimension. And health equity is a theme that gets talked about a lot in US healthcare. I think in, in most countries, you know, your quality of healthcare tends to follow your socioeconomic class or your zip code where you live. And so, it’s really rooted here in the mission that we’re here to empower all people. Now that said, you can say that and you can write it and print it on the wall and print it in your presentations, but you still have to act and turn those words into execution.

We’ve had very coordinated, let’s say, projects or efforts, you know, the how we do things when it comes to, for example, women in leadership or black professionals in technology. And I’ve had a very I would say coordinated plan around women on our overall leadership team. My first independent board member. You know, often in boards, especially early stage, you kind of get who you get from your investor and I feel like that’s starting to change, but it’s, you know, it’s something that has some structural challenges, but on independent board members you can absolutely make decisions and choose people that, you know, bring a diversity of thought and a diversity of, you know, race, religion, orientation, et cetera. So, we’ve been very deliberate, and we’ve measured, and we quote those statistics because we’ve been measuring them to the degree that we can. I mean, not everybody wants to provide that information and I understand, I understand that, but to the degree we can, we measure it, and we observe areas that are at risk for, you know, unconscious bias and the hiring process is a big part of that onboarding process is a big part of that performance management.

So, I’d say overall we’ve been very systematic. There’s a lot to be proud of. I was the kid got a trophy and looked at it on the mantle for a day and then took it down the next day because, you know, yesterday’s trophy is not as important as the one that we’re going to get tomorrow. So yeah, we still have plenty of work to do. , being in Toronto, which is where, you know, one of our HQs is having a, I think it’s 49% non-white diversity is actually, I don’t want to say it’s easy but Toronto is , you know, it’s a cultural wonderland. Like there’s people from everywhere here. So, I wouldn’t give us super high marks on that alone. But having people of diverse backgrounds in leadership positions in the board and the, you know, the executive team and then, you know, driving this more broadly, like having an engineering team that is so diverse and in particular strong women leadership, I think that is, that is unique. So, I’m really proud of what we’ve done, but lots more to do.

Ed (43:17): You should be proud you’re leading the way without doubt. Part of this to me also plays into this policy that League has around work your way, I think you call it, which gives all the Leaguers an opportunity to, to really define how they want to work, where they want to work, and scheduling around that. This is a hot topic as you can imagine at the moment coming out of the pandemic and many CEOs are up and down and in and out of offices and haven’t really settled on a clearly defined policy. But just having heard you speak so passionately about diversity becomes very clear. While this policy is such an important part to league.

Mike (43:56): It’s funny, you know, it only became a policy in writing in recent, the recent, you know, 12 to 24 months. But we kind of always had that mindset. I mean, League did not discover Zoom and Slack because of the pandemic happened. League did not discover come to an office or stay at home because of pandemic happened. We kind of worked that way beforehand and honestly it kind of started with , you know, mine and Dan and Dan’s and Todd’s, you know, experiences built several companies over the years and honestly some of the structure and some of the norms that are from television or the movies or, or popular culture norms about the office I mean some of them are just without a lot of merit. , so we’ve always had a kind of work your way mentality.

You know, we’ve always had a, you know, a family first. I mean this is a work family, but you have your family, and you know, life happens, you know, you don’t have to be in the office if something is wrong at home or you’ve got to deal with something at home. So that’s always been us enter pandemic and you know, we kind of took an early stance. I mean, I remember I was on spring break with my kids and my wife. We were in Hawaii, we cut that trip short, we went early to kind of virtual and by August of that same year of 2020 we started to open again. I was a part of a separate from League a part of a national rapid screening program, introducing it and this idea of getting people back to life into being social in a healthy way and to be working in a healthy way, safe way.

So, I was kind of adamant about the office needs to be an option, but it’s not going to be an option for everyone and it’s not going to be an option that makes sense for everyone all the time. So, we’ve put some structure and some meat on the bone, so to speak, to what hybrid and work your way means. But I will tell you, and I, I’ll be totally candid here, I regularly am hearing everyday part of all sorts of different, you know, CEO groups and chat groups and you know, friend groups and a lot of my friends who are, you know, leading companies are flipping to everyone’s got to be back in the office, the hard mandate. And I know there’s anxiety around that. I’m sure it exists in the, the walls or the slack walls. Even at League and I, I try to reiterate, I write something every week called TWA the Week ahead, which I write every Monday or Sunday since the beginning of League something I post’s very transparent and it’s one of the things I reiterate like where we believe in this hybrid model work your way.

And that’s not new, it’s just better than it was two years ago. But I am thinking about what are the ways we can be pushing it forward and adapting it and making it better. Because I also know that, you know, it takes hard work, and it takes teamwork to build an awesome enterprise and change an industry. And sometimes that is just really hard to do for certain functions or certain goals in a completely remote way. I just, I haven’t figured it out yet. And if Dan were here, he’d be like, Mike is mostly right, but there are exceptions that I disagree with him on. That’s okay. So, work in progress, but I don’t think we’re done. We’re not going back to a hundred percent in office all the time. We were never there. We’ve hired hundreds of people that are not in Toronto or Chicago. So, it’s like structurally now not easy for us to go back to that anyway. Even if we, we wanted to and frankly this version is better cause we found great people in places we otherwise wouldn’t have found them. So, a lot of work to do, still not done. But I think the core principles around work your Way make a lot of sense and they do work. We’ve never been more productive.


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