League Employee Spotlight: Meet Andrew!

by: | May 9, 2017

Ever wonder what it’s like behind the scenes at League? What type of people make up our ever growing team, and what do they do to help us build a product that is revolutionizing health insurance, employee benefits and workplace wellness? Starting today, you can stop wondering. Each month, we’ll be featuring one of our talented team members in the new League Employee Spotlight series.

1.  What drew you to League and to your role?

League’s mission and League’s team.

I spent time early in my career working for a mix of healthcare and technology companies as a strategy consultant—and then tried (unsuccessfully) to start a healthcare IT company while completing my MBA. As I look back, I’ve somewhat serendipitously been on a path toward building a company that gives people the insight and resources needed to be healthy. League’s mission to empower people to be healthy every day fits that same bill.

The opportunity to pursue that mission with a team of experienced entrepreneurs and operators, at home in Toronto, sealed the deal for me.

I’ve often felt that the most transformative new products, the most exciting innovations come from people outside of an industry. That’s what I saw in the team at League: A collection of talented people asking fundamental questions about why healthcare and health insurance work the way they do.

It’s those kinds of questions that I ask myself every day as we work to build an entirely new kind of health benefits company.

2. What do you love about your job?

I like to say that I’m a “recovering” strategy consultant.  

What I love about my job at League is that I don’t just ask the fundamental questions about why things are, or propose how they might be done differently, I actually do them.

League is my third stint in the wild west that is startups—and what keeps me coming back to the frontier is the opportunity to build a company, from scratch, irrespective of the odds. To do that in the context of rethinking health, wellness and benefits (with a tangible impact on our members’ lives) is a real privilege.


Check out our careers page to join the League team.


3. What are the key assets to kick ass at League or in today’s startup environment in general?

One of League’s core values is “Own it. We trust you.” Though the words are unique to League, the sentiment is not.

From what I’ve seen at League and elsewhere, the most successful startup employees are genuinely excited to grab the ball and run with it. They attack problems with vigour.  They get work done with little direction. And they focus on what actually builds the business—and relentlessly avoid being busy for the sake of being busy.

Startups are inherently an environment without much structure—or at least as much structure as a large corporate environment. I’ve often compared startups to basketball, whereas Fortune 500-type companies are much more like football. In basketball, you draft the best athletes—the athletes that can play multiple positions—versus the best specialists like you would in football.

That adaptability, that willingness to tackle any challenge is what employees need in a startup—irrespective of the “position” they “play” in sales, engineering, finance or strategy.

4. What would you say to a recent grad looking to either get into League, or follow your career path?

I’ve increasingly let go of the traditional idea of a “career path.” I don’t entirely believe that the concept applies given how the work world is structured today—or at least that the concept doesn’t apply in the startup world.

Instead, I’ve tried to focus on my personal “themes” and to spend my time (most of which happens at work) on my themes. For me, they are:

  1. Build a company from “zero to one” at the intersection of healthcare and technology
  2. Support millennial, Canadian entrepreneurs in their quest to build the “next” great technology-driven company
  3. Reshape the dialogue and stigma related to mental health

My one piece of advice whether you’re interested in League, a startup or another profession: Be clear about your themes.

I believe that the world leaves us little clues about what our themes are—or what they might turn out to be. If we’re mindful of the clues, we’ll find the themes that guide our actions and frame our “path.”

5. Maintaining good personal health is vital to ensuring employees are able to perform at their highest standard. What is it about your health regimen that elevates you to be your best self at League?

Over the last year, I’ve developed my own personal health program that combines fitness, including yoga, nutrition and professional support. I’m not a believer in “silver bullets,” but have found that this combination keeps me physically fit and mentally strong.

Our CEO, Michael Serbinis, has often said that startups are like a “marathon sprint.” I treat my health regimen as my “work outside work” that helps me perform at my highest level (during the marathon and the sprint).

And it’s League’s benefits (such as our Health and Lifestyle Spending Accounts) that have allowed me to bring my health program to life through yoga classes, nutritional seminars, and working with healthcare providers that also work with Olympic athletes.

I’m not sure they’re as excited to work with me as I am with them!

6. What is your favourite perk at League?

Can we consider the people a perk?

If not, sparkling water on tap?

No, no… standing desks!

7. What is the one material item you would bring with you to a deserted island?

Satellite TV… so I can watch Toronto Raptors basketball.  Let’s go, Raptors!

8. Tacos or Pizza?

Tacos. From Border Cafe.

My Boston friends know what I’m talking about.


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