Janet Bannister’s firm Staircase Ventures offers more than just money and advice to founders – it also pays for coaches, financial advisers and even child care.Fred Lum/the Globe and Mail
Janet Bannister’s gambit to bring caring and sharing to the high-risk venture-capital business appears to be paying off.
Ms. Bannister, one of Canada’s best-known startup financiers, has raised $32-million for the second seed-stage fund of her firm, Staircase Ventures, two years after topping out at $34-million for her inaugural fund.
Ms. Bannister said her Toronto-based firm hopes to reach $40-million for the second fund in early 2026 despite the continuing overall fundraising challenges in the Canadian venture-capital sector.
Returning investors Royal Bank of Canada and Northleaf Capital Partners are anchoring the fund, which seeks to initially invest $1-million to $2.5-million in primarily Canadian software startups with early customers and clear market traction.
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Others backing Staircase for a second time include Mike Wessinger, co-founder and executive chairman of PointClickCare Corp., one of Canada’s largest private technology companies, and ex-Shopify chief product officer Craig Miller – both advisers to Staircase.
Tim McGuire, former leader of McKinsey & Co.’s global retail practice, who has known Ms. Bannister since she worked for the consulting giant, is also an investor.
The first Staircase fund has generated an average 50-per-cent annual internal rate of return to date – placing it among the top 10 per cent of North American funds launched in 2023 – though those early, paper gains haven’t yet crystalized into cash for investors.
Four of the 12 companies Staircase has backed have raised follow-on capital at higher valuations, including drug discovery startup Biossil Inc., led by Anthony Mouchantaf, former director of venture capital with RBC’s innovation banking unit.
Another Staircase portfolio company, Calgary-based Fillip Fleet, which provides digital fuel credit cards to fleet operators, has signed deals with Telus and Circle K.
“I’m very happy with the success of fund 1 and we have proven out the Staircase Ventures model,” Ms. Bannister said in an interview. “We want to replicate that success and maintain the same strategy with a small fund so we can be selective and really focus on getting into the very best companies in Canada.”
Ms. Bannister gained renown by overseeing the launch of the Kijiji classified business when she was an executive with eBay Inc. in the 2000s.
She became a venture capitalist in 2014, joining Montreal-based Real Ventures, where she led investments into League Inc., BenchSci and Clutch. She became managing partner and despite fixing some issues stemming from a period of inner tumult that preceded her leadership, Real was unsuccessful in raising another fund. She left in 2022.
With Staircase, Ms. Bannister decided to double down on her reputation for providing high-touch support to founders by offering more than money and advice.
Her firm pays for executive and health coaches and financial advisers for its founders and provides cash for their child-care, elder-support or other family needs. Staircase also pays to connect founders with peer support groups and puts its advisers and investors to work helping portfolio companies.
“It has to be a competitive advantage when she’s talking to founders about investing, because they know they’ll get more from her than a typical fund that just writes a cheque,” said Mr. McGuire, who has advised Fillip on strategy.
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A Staircase investment comes with another unusual perk: Staircase-backed founders collectively share in one-fifth of Ms. Bannister’s investment gains, or carry, that she earns from fund investments.
Staircase has led some investments into companies created by repeat founders, including Toronto’s Una Software Inc., an AI-powered financial-planning software provider co-founded by Don Mal. He co-founded Vena Solutions Inc., one of Canada’s largest private technology companies.
“It wasn’t so much the money but the non-capital reasons” that prompted Una to choose Staircase to lead a $5-million financing this year, he said.
Mr. Mal praised Ms. Bannister for continually engaging with Una’s leaders and for regularly connecting the company to other portfolio companies and advisers. “She’s an amazing sparkplug and positive influence” he said.
Mr. Wessinger, of PointClickCare, said in an interview: “I don’t know anybody that works harder than Janet.”
He was initially skeptical about the Staircase model, “but it seems to be working, and appeals to founders so much that they would turn down other quality investors in favour of her,” he said.
“It’s unfolding exactly how she promised.”