The noted Canuck transplanted himself in 1998 from Goderich, Ont. to Silicon Valley, where he will be based for the venture capital outfit. Sagard also announced Jonathan Tétrault, until recently the second-in-command at Cirque du Soleil, as its new managing partner. (La Presse)

Talking point: O’Neill is expected to add heft to Portag3’s crop of investments, as well as help devise strategies for the fund and for Sagard Holdings, the Desmarais-owned asset manager that oversees Portag3. A proponent of Google X, the company’s impossibilist lab, O’Neill focused on wearables during his decade-long stint at Google Canada—one of the notably noble failures of the company. As an investor and adviser, O’Neill also helped secure exits for Relay, Layer6 and Helpful. In December 2019, Portag3 closed a $427-million early-stage fund, the largest of its kind in Canada.

The Winnipeg-based company, which uses artificial intelligence to gauge the effect of financial-planning decisions on long-term savings health, has raised a total of $4 million since launching in 2018. (The Logic)

Talking point: The bet on Conquest Planning marks the first Canadian investment for Portag3 since it closed its $427-million second fund in December. Clearly, the Toronto-based early stage venture capital firm likes what Conquest is offering, which is simplified financial tools for the hoi polloi: In October, Conquest won $1 million from Portag3 via Finance Montréal’s Start-up Pitch contest.

Existing anchor investor Portag3 Ventures—the fintech arm of Power Financial—led the investment in Diagram, which uses its money to co-found new businesses with entrepreneurs in financial services, health care and insurance. Angela Strange, a partner at Andreessen Horowitz, and Bruce Heyman, the former U.S. ambassador to Canada and former managing director of Goldman Sachs, were among the high-profile angel investors who also participated in the fund. (Financial Post)

Talking point: Access to Diagram’s portfolio companies could help Power’s core insurance operations understand what new technologies to apply to their businesses. In the past, the firms have also matched up the startups in which they have invested to increase their chances of finding customers. In 2017, one of Diagram’s first investments, Dialogue, integrated its service—which allows customers’ employees to chat with doctors—with benefits platform League, a Power Financial portfolio company. A year later, Power Corp. subsidiary Great-West Life launched Dialogue to employers across Canada. Power and its subsidiaries own robo-adviser Wealthsimple, while Portag3 has invested in digital account service Koho and Borrowell, which provides credit scores and facilitates personal loans. The startups in Diagram’s second fund could benefit from the customer base of those existing scale-ups.

Sun Life is investing $32.7 million for a minority stake in Dialogue. A number of existing investors, including the Caisse de dépôt et placement du Québec and Portag3 Ventures, participated in the round. (The Logic)

Talking point: The investment comes as Canadians are increasingly turning to virtual health care due to the pandemic. Sun Life has the right to exercise additional options under the deal, but will remain a minority shareholder even if it does. In May, The Logic reported that Dialogue had quadrupled its workforce from 250 to 1,000 during the pandemic and was looking to add an additional 150 staff. The fresh financing will be used for acquisitions as well as an expansion into virtual treatments for chronic diseases and women’s health services. The Canadian telehealth market is growing increasingly competitive. Telus and Morneau Shepell have made deals with provincial governments during the pandemic to provide services. Other firms, like OnCall Health and Well Health, are also seeking to carve out more of the market.

The round, led by Portag3 Ventures, will allow the Toronto-based company to further develop Boosted Insights, its AI-based investment tool. Founded in 2017, the company has raised a total of $11 million. (The Logic)

Talking point: Boosted’s AI-based product uses machine learning to highlight market patterns. Canadian SaaS purveyors harvested over $5 billion in investment in 2019.