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Wealthsimple in its $750-million Series E round at a post-money valuation of $10 billion

On October 27, 2025, Wealthsimple announced that it has signed a Series E round of up to $750 million at a post-money valuation of $10 billion. The round, which includes both a $550-million primary offering and a secondary offering of up to $200 million, is co-led by Dragoneer Investment Group and...

Lead Office: Toronto Date Announced: October 27, 2025 Value: $750 million

Wealthsimple in connection with Tetra Trust’s $10-million financing

On September 8, 2025, Tetra Trust announced that its new parent company, Tetra Digital Group, closed $10 million in funding with investors including Wealthsimple, Shopify, National Bank, ATB Financial, Purpose Unlimited and Shakepay. Tetra Trust will use the new capital to launch a Canadian-dollar...

Lead Office: Toronto Date Announced: September 8, 2025 Value: $10 million

Tailscale in its US$160-million Series C financing

On April 8, 2025, Tailscale announced that it raised US$160 million of Series C financing. This round was led by Accel and had participation from returning investors including CRV, Insight Partners, Heavybit and Uncork Capital. Tailscale plans to utilize the funding towards its global expansion...

Lead Office: Toronto Date Announced: April 8, 2025 Value: US$160 million

Ribbon AI in its $8 million financing

On March 31, 2025, Ribbon AI announced that it raised $8 million of funding. This round was led by Radical Ventures and had participation from Social Leverage, Cadenza Ventures and GD1. The company plans on utilizing the funding towards expanding operations and development initiatives. Ribbon...

Lead Office: Toronto Date Announced: May 31, 2025 Value: $8 million

StructureFlow in its acquisition of Blue J Diagramming

On February 18, 2025, StructureFlow announced its acquisition of the Blue J Diagramming platform from Blue J Legal. Following this acquisition, Blue J Diagramming customers will be migrated to StructureFlow, which is part of a greater strategic shift to leverage its generative AI solution for tax...

Lead Office: Toronto Date Announced: February 18, 2025 Value: --