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PSPIB and Sun Life participated in a US$205-million round for San Francisco-based Collective Health, which offers software that helps U.S. employers manage their health insurance programs, including financial reporting and administration. Employees can use Collective Health to review claims and spending and chat with customer service on one platform. SoftBank led the round; Collective Health will use the funds on product development and growing its engineering team. (The Logic)

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Talking point: The investment comes as other Canadian pension funds are ramping up their tech investments; the Canada Pension Plan Investment Board is planning to invest up to $1 billion in venture capital funds to understand how tech investments can shape or disrupt its existing portfolio. And, in May, it participated in the US$350-million close of Radical Ventures, a new Canadian artificial intelligence fund. The Ontario Teachers’ Pension Plan appointed Olivia Steedman in April to lead a new investment department dedicated to tech companies. For Sun Life, it’s an opportunity to have a stake in another tech company, as it navigates the disruption in the insurance industry; in 2018, Sun Life launched Lumino, an online portal that has ratings and costs of Canadian health providers in a marketplace that resembles the first iteration of League, which allows employers to manage health insurance for employees.

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Gildan’s Glenn Chamandy was the top Canadian in the Harvard Business Review rankings, at 49th place. Bell’s George Cope and Sun Life’s Dean Connor also made the list, which looks at both financial and environmental, social and governance (ESG) performance. (Harvard Business Review)

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Talking point: This is the first time since 2014 Bezos hasn’t come first—and he didn’t even make the top 100, largely because of a methodology change that increased the importance of ESGs in the rankings. Harvard Business Review changed its methodology because both companies and investors are increasingly focused on more than just the bottom line. In August, for example, the CEOs of 181 of the most powerful companies in the U.S. announced that a corporation has a broader social remit and should not focus solely on helping shareholders. The Canadian CEOs on the list were generally bolstered by stronger ESG metrics than financial ones. Brookfield Asset Management’s Bruce Flatt was an outlier; although he did much better on financial performance than any other Canadian CEO—reaching 25th place overall—he ranked 855th on one of the ESG metrics.

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Three-quarters of the money will be invested into venture capital funds, with the remaining quarter going to later-stage scale-ups. Northleaf has previously invested in Canadian firms like Shopify, Wattpad and Ecobee. In June 2018, the VC fund was named one of the winners of the federal government’s Venture Capital Catalyst Initiative, which split $350 million among five fund-of-funds. (Globe and Mail)

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Talking point: The Business Development Bank of Canada, the Canada Pension Plan Investment Board, Sun Life Financial and TD Bank have all invested in the fund. But it has also attracted capital from outside the country, including from Asia. Ian Carew, Northleaf director, said Canada has historically been overlooked by international investors considering North America. U.S. investors continue to be the major foreign players in the Canadian VC market, however—they accounted for 52.8 per cent of funding in Canadian tech companies in the first quarter of 2019, according to CPE Media.