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Michael Serbinis, League founder, works with Christine Noonan, a Toronto-based yoga instructor and an early adopter of League, in his home in Toronto.

Glenn Lowson/The Globe and Mail

The series: We look at decision makers among Canada's mid-sized companies who took successful action in a competitive global digital economy.

Initially, Mike Serbinis founded League Inc. as a way to redefine the future of health care, operating an Uber-like platform for customers to access wellness services. So whether a client wanted a Swedish massage or an eye exam, finding a provider, scheduling an appointment and paying for that service were a few smartphone taps away.

But even as that business flourished after getting off the ground in 2015, he was constantly hit with the same question from human resources personnel and company executives using his platform.

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"Why wouldn't you provide the entire experience for my health benefits?" he says they told him. "Why would I give my employees what looks like an Elon Musk rocket ship and then for the rest of their benefits have them drive around in an old Lada? Makes no sense, so why wouldn't you do the whole thing?"

So in the summer of 2016, Mr. Serbinis and his team of 30 or so employees decided to also use their platform to go after the traditional health insurance industry and to leave behind paper booklets.

Starting with RBC Insurance as its first partner to underwrite its offerings, League introduced a full suite of insurance products through licensed subsidiary League Insurance Agency Inc. The resulting smartphone app and website gives customers a 100-per-cent digital experience, allowing employers to tailor an a-la-carte solution to its employees' health and insurance needs.

Mr. Serbinis describes it as the time where the company had to decide whether it wanted to be the elephant or just merely the fly on the elephant.

"It was a bet-the-company moment," he says. "We could continue on [the way we were] but over time we might also get elbowed out by somebody bigger that says … I'm providing the rest of the service to the client."

Though he didn't understand exactly how he was going to do it, he determined he had to do it anyway, and learn what he didn't know as he went along. As the co-founder of both document security company DocSpace and e-book reader company Kobo (both of which he had previously sold), Mr. Serbinis was no stranger to disruption.

"I've heard, 'Oh, this looks impossible, what are you thinking?'" he says. "To me that's a signal that I might be on the right track."

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With today's consumer more concerned with prevention than treatment, he knew that employees expect their employers to be a stakeholder in their health and workplace health benefits form a big part of that. However, getting insurance companies to adopt new technology was not easy, particularly as they were being asked to fix something that wasn't entirely broken.

Mr. Serbinis admitted that even as a CEO that understands technology and entrepreneurs, he doesn't always trust the new guys on the block, so he understood the hurdles his company faced. He also knew how to overcome them.

"Earning people's trust and getting credibility meant starting small and getting an account in the door and doing right by that employer and their employees," he adds.

So League started with restaurants and manufacturers, brewers and farmers and built its way up from there. Exactly 12 months later, its customers include companies such as Shopify and employers with thousands of employees.

Mr. Serbinis says that business in 2017 is 40 times what League did last year, and the company has grown to about 130 employees as a result.

"Now we're expanding into the United States, and there we have a market where it's not only a lot more people but they spend a lot more money, or employers do," he says, estimating that U.S.-based companies spend three to five times more per employee in offering health insurance.

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Innovation is key to the company's competitiveness, one consultant says, but companies should beware before striking out in a different direction.

"It's innovative and a lot of organizations struggle in the innovation space," says Sandi Verrecchia, president and chief executive officer of Satori Consulting Inc. in Burlington, Ont. "For them to listen to their customers and be able to be flexible enough to innovate in something like that, kudos to them."

In some ways, the success of League's decision was also helped because health insurance was a complementary product to the health benefits that it was already offering. In that regard, Ms. Verrecchia says the progression to insurance was a natural fit, but companies should beware of new directions that don't mesh with their business strategy.

"When it doesn't align with where they're going and they're trying to shoe-horn it in, because they think it's interesting or somebody has a passion for it, that's when things start to fall off the rails," she adds.

League's decision to streamline services, to add insurance to health benefits in a one-stop online portal shop, as it were, should also make it an easier sell to clients.

Sally De Rosa, the human resources lead for business strategy consulting firm Diabsolut Inc. in Montreal, says that today's business world is all about business leaders trying to centralize focus. So multiple systems and platforms can actually be detrimental to a firm's success.

"Make the user experience as smooth as possible, so they can focus more directly and intently on the things they're meant to be focusing on," she says.

But the company needs to be proactive about explaining to customers how the company's decision benefits them, Satori Consulting's Ms. Verrecchia says.

The marketing side, particularly of a complementary product, may be as important as the innovation of the product itself, she says.

"Especially if you've had a long-term customer base that knows you," she says. "Trying to get them to understand why you've expanded is fine, but how it benefits them, what's in it for me as a customer, is really what you need to convey."

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