League enters 2022 as Canada’s newest unicorn with TDM Growth Partners-led round

League's Michael Serbinis
League will watch the ball drop with a billion-dollar valuation.

In a historic year for valuations, League‘s new funding round has squeezed in one more Canadian tech unicorn before the clock strikes midnight on 2021, BetaKit has learned.

Sources confirmed to BetaKit that the Toronto-based healthcare startup has raised $70 million USD in new financing, which closed today. Those sources, who wished to remain anonymous because they are not permitted to speak on behalf of the company, indicated that the pre-money valuation of the financing priced League at $850 million USD, or $1.1 billion CAD, making it Canada’s newest tech unicorn.

Sources indicated that the pre-money valuation of the financing priced League at $850 million USD, or $1.1 billion CAD, making it Canada’s newest tech unicorn.

Per Crunchbase, the new investment puts League’s total financing at over $140 million USD. Notable past investors include Telus Ventures, Wittington Ventures, RBC Ventures, OMERS Ventures, Portag3 Ventures, Real Ventures, Manulife, and BDC, among others.

The investment was led by Sydney, Australia, and New York-based TDM Growth Partners. The firm has invested in a variety of notable tech companies, including Square, Twilio, Spotify, and Canadian-bred Slack.

TDM could not be reached for comment by time of publication. When reached by phone, League CEO and founder Michael Serbinis declined to comment.

A spokesperson for League told BetaKit the company was “in the midst of fundraising and are speaking to multiple potential investors but can’t provide any information at this time.”

UPDATE 01/02/2022: One month after League closed the $70 million USD the company announced it has secured an additional $25 million. This brings the total round size to $95 million, with Workday Ventures and existing investors taking part. The company says this brings League’s total funding to date to $205 million.

It has been a long road to unicorn status for League and its founder – who had once set the ambitious goal of reaching a billion-dollar valuation by 2018. Founded by the serial entrepreneur in 2014 after selling e-reader startup Kobo to Rakuten for $315 million USD, the initial vision of League was that of an Uber for healthcare services, allowing users to find, connect, and chat with medical professionals and health practitioners in their local area.

A look at the League app from its Canada launch in 2015.

“We’re building a data-rich mobile platform that will focus on prevention and give people the power to take control of their health,” Serbinis told BetaKit prior to League’s Canadian launch. “We want to help people stay healthy every day, to connect them with a wide range of health professionals and personalized services through easy-to-use mobile experience.”

At that time, the company was already exploring partnerships with insurers and employers, and by 2016, League was raising money from insurance and finance strategics like Manulife and Power Financial. Later that year, League added former Sun Life Financial executive Lori Casselman (now president of Toronto-based Wello) as chief health officer, before launching insurance products with RBC.

“In the nine months that we’ve been selling our benefits platform, the bulk of sales has been in spending accounts or health and wellness services,” Serbinis told BetaKit in 2016. “And over that time, we’ve had an overwhelming demand from customers who say ‘this is such an amazing experience, the paper and all these forms and frustration with existing health insurance is so out of date and difficult, so why can’t you provide health insurance?’”

By 2018, League didn’t have a billion-dollar valuation, but it did have a $62 million CAD Series B round led by Telus Ventures, and a growing portfolio that included AETNA, Humana, Cigna, United Healthcare, and MetLife as insurance partners.

Since then, the company has appeared to put a greater emphasis on building the technology infrastructure to power digital health experiences for providers, payers, and consumer health practitioners.

Per Crunchbase, League raised an unannounced ‘corporate round’ in 2019, shortly after launching its Health Benefits Experience (HBX) platform. By February 2020, League was offering its HBX to wealth management and benefits provider Canada Life‘s customers. Months later, the company announced its ‘Powered by League’ partner program to power digital health infrastructure for pharmacies, health systems, and financial institutions. By the end of the year, League had partnered with Loblaw Companies to build the grocery giant’s new health-focused app, PC Health (Wittington Ventures is also notably the subsidiary of a holding company owned by the Weston family, which also owns and operates Loblaws). League also signed agreements in 2021 to build the health and benefits and benefits platform for Humana, the third-largest health insurance provider in the United States.

Just in under the wire, League joins a growing list of Canadian tech companies to secure a unicorn valuation in 2021, including Trulioo, Ada, Blockstream, Dapper Labs, Clio, FreshBooks, and Clearco.

Douglas Soltys

Douglas Soltys

Douglas Soltys is the Editor-in-Chief of BetaKit and founder of BetaKit Incorporated. He has worked for a few failed companies and written about many more. He spends too much time on the Internet.

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