Staircase Ventures is a Toronto-based seed-stage venture capital firm founded in 2023 by Janet Bannister, one of Canada's most recognized startup investors. The firm was built around a single premise: that by investing in the development of founders as people, not just their companies, you can meaningfully change the trajectory of those businesses. Two funds in, the firm has established itself as the most founder-development-focused VC in the Canadian ecosystem.
Staircase invests primarily in Canadian B2B software companies that use technology to deliver measurably better efficiency or effectiveness to their customers. The firm looks for companies with a product already in market and early signs of product-market fit. Approximately half the current portfolio has LLMs at the core of the product; the other half leverages AI to enhance an existing offering.
Staircase closed Fund II at $50 million CAD in March 2026, exceeding its original $40 million target in an oversubscribed round. More than 80% of Fund I LPs returned, alongside new investors including BDC Capital, the University of Alberta endowment, and InBC Investment Corp. (British Columbia). Other LPs include Royal Bank of Canada, Northleaf Capital Partners, PointClickCare co-founder Mike Wessinger, and former Shopify CPO Craig Miller. Fund II plans to invest in approximately 12 companies with initial checks of $1M to $2.5M, reserving 40% of capital for follow-on. The first investment from Fund II has already been made in MedEssist, a Toronto healthtech startup helping independent pharmacies modernize operations.
Leadership
Janet Bannister is Founder and Managing Partner. She previously served as Managing Partner at Real Ventures, where she led investments in BenchSci, Clutch, and League. Before that she founded and scaled Kijiji.ca at eBay, growing it into one of Canada's most-visited websites. She is Co-Chair of C100 and serves on the boards of Communitech, the Vector Institute, and Ivey Business School. Andrew Tiffin joined as Operating Partner in early 2026, bringing experience from Shopify (Chief of Staff to the CRO), Uber Eats, Clutch, and strategy consulting at Monitor Group.
Investment Strategy
Staircase leads pre-seed and seed rounds with checks of $1M to $2.5M, targeting a concentrated portfolio of approximately 12 companies per fund. The firm invests in Canadian companies, most of which target North American or global markets. Its five-pillar Founder Development Platform is a defining differentiator: founders receive executive coaching (6 to 12 months of one-on-one sessions), peer support groups with other founders across North America, a dedicated Cleveland Clinic Canada health coach, a personal financial advisor specializing in tech founders, and parenting and family support. Staircase also shares 20% of its carried interest with founders and advisors, aligning the entire portfolio community around shared upside.
Notable Investments
The Fund I portfolio of 12 companies includes:
Other
Five of the 12 Fund I companies have raised follow-on financing at higher valuations. The shared carry model creates an unusually collaborative portfolio community: founders have a financial incentive to support each other, and Staircase deliberately facilitates this through peer groups, founder offsites, and advisor introductions. The advisory board includes founders and operators who have built $1B+ businesses. Staircase is one of the few Canadian funds to make personal wellbeing a contractual part of its investor-founder relationship.
Canada
