League Employee Spotlight: Meet Stew!

by: | February 9, 2017

Ever wonder what it’s like behind the spotlight 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? Now you can stop wondering. Get to know our talented team members in the new League Employee Spotlight series.

Where are you from, what did you study and why?

I was born and raised in Toronto, though a big piece of who I am stems from my summers spent on an island out in Georgian Bay. The cottage probably isn’t the typical place for nurturing the entrepreneurial spirit. But for me, this was where a lot of my passions and creativity started to germinate.

While I studied communications and business administration at Wilfrid Laurier University, I had always had a passion for industrial design/industrial engineering and the efficiencies that are integral to such work. As I took a different path school/career-wise, this naturally turned into my #1 hobby.

What led you to the sales field?

A lot of the time you hear things like, “I fell into sales.” But for me, it was quite the opposite. It was the result of my ruthless pursuit to combine all of my passions—designing concepts, analyzing data, forging relationships, coaching and learning—with my natural competitive drive.

It really began in my third year of university, when I convinced a startup founder to hire me for a two-week trade show stint he was going on. During that time, I created a lead list of 340 prospects, and rolled out a drip campaign shortly thereafter. Once I had left, the leads started funneling in—he ended up hiring me two weeks later. I was going into my fourth year of school, and I was suddenly the new Sales and Marketing Manager at a two-man tech company, one that had yet to bring its product to market.

When the CEO handed me a credit card and told me to go buy some desks (and a coffee machine!) for the office, it made me realize how comfortable I was with the uncomfortable. It also triggered my entrepreneurial aspirations from the past, and solidified my passion for risk and ownership. My startup sales career had begun.


Check out our careers page to join the League Team.

What do you love about your job?

In sales, you have to truly believe in what you’re selling, so the fact that we’re solving a real problem at League (enabling people to be healthier) makes my job easy. My family has experienced a lot of serious cardiac issues over the years, so working in a field that encourages preventative health is important to me. Making sure the battles you fight in your everyday life align with what you do at work every day helps ensure you’re pursuing something you’re passionate about.

At League, we are redefining SaaS sales, while building an incubator for future sales leaders. No two days are the same and that’s exciting. I love making people feel comfortable in what can be an uncomfortable environment. I love teaching, building and owning a company revenue target. I love how we blend data, process, strategy and great people together to build something pretty amazing from scratch. I love the rush and ownership. The revenue numbers my team posts each month are the numbers our executive team presents to the board—I like that pressure.

And finally, and most importantly, I love my team—it’s why I come into work every day, excited and pumped to win—the people who make up my team make my day. We’ve got a really special group here at League. The sales crew is going on 30 people and will be climbing to 100 by the end of the year. We have a wild ride ahead of us.

What do you think are the key assets to kick ass in today’s sales environment?

Creativity and curiosity are vital. When starting off, coachability is an overseen quality that forecasts huge potential. In our business here at League, reflection and refinement are key to our success. I would say that they’re important in all sales organizations. Just because something is working today doesn’t mean it will work tomorrow. When you achieve success the best thing to do is step back. Outline the things that helped you get there and the hurdles you overcame, then share that with the team so everyone can achieve the same success… faster and with fewer hurdles.

In sales, if you get in the habit of reflecting when you succeed, you will build a routine that demands excellence. You’ll achieve success today, but you will always be hungry for 10 times that success tomorrow. Nobody wants 0% month/month growth—how do we do 10 times more, how do we win faster, how can we share our learning with the team so they can achieve the same success in half the time?

What would you say to recent graduates wanting to enter this Field?

There used to be a stigma around sales—but the days of a “used car salesman” persona are dead. Sales is very calculated and strategic. It combines a bunch of different elements that most people think are completely unrelated to sales like data, process, psychology, strategic communication and methodology, to name a few.

You very much get what you put into sales. You can’t just go to the gym one day and achieve an optimal level of fitness. You have to work hard and keep your head down and in time, you will achieve those goals. You’re tearing muscle fibres and need time for them to heal; similar to trial and error in sales, experience makes you stronger. Sales is the same way: results come after weeks and sometimes months of hard work on deals, and years of work in terms of strategy. That being said, you must be dedicated and passionate about what you’re selling. If you love going to the gym, becoming fit will be a blast…. If you love what you sell—and the company you work for, and the people you work with—putting in the work and watching it come to fruition is an incredible rush.

Quirky factoid about yourself:

I love working with my hands, specifically building furniture with reclaimed wood. I also own a show goat that finished second in show at the Royal Winter Fair (don’t ask).

League is hiring!

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.