Chexy raises USD $14 million to widen payments push

Canadian fintech Chexy has raised USD $14 million in a Series A round led by Khosla Ventures, with follow-on investment from Air Canada, as it expands beyond rent payments into utilities, taxes and business outgoings.

The Toronto-based company will use the funding to expand its payments platform across Canada, add partners and hire staff. Chexy lets consumers and businesses use credit cards for payments that often do not accept them directly, allowing users to earn points or cashback on expenses such as rent, childcare, personal and property taxes, payroll and vendor payments.

The round gives Chexy backing from a Silicon Valley investor known for betting on large technology companies, while deepening its ties with Air Canada through Aeroplan. That partnership allows users to collect loyalty points on recurring household payments and other large bills.

Chexy says it now has more than 200,000 users across Canada, who have earned more than USD $35 million in rewards and cashback since the business launched in 2023.

The company first gained traction among renters looking to earn travel rewards on monthly housing costs. It is now widening its focus to homeowners and small businesses, reflecting rising demand for ways to extract more value from essential spending as household budgets remain under pressure.

Wider Scope

Chexy's model targets a gap in the payments market: many of the largest regular expenses faced by households and smaller companies cannot usually be paid by credit card, or are difficult to put on one. Chexy processes those payments on behalf of users and links them to rewards cards, creating a way to earn points and cashback on transactions that would otherwise generate nothing.

The approach also appeals to small and medium-sized businesses, which use the platform for payroll, tax bills and supplier payments while managing short-term cash flow.

Chexy remains focused on Canada and has no immediate plans to enter the US market. That stance stands out at a time when many Canadian technology companies have looked south for deeper pools of capital and faster growth.

Against that backdrop, the latest round suggests investors see room to build a larger financial services business focused squarely on Canadian consumers and businesses.

"Before Chexy, an entire category of earning simply didn't exist. Trillions of dollars in essential payments - rent, taxes, and bills - generated zero rewards. We built Chexy to change that," said Liza Akhvledziani Carew, co-founder and CEO of Chexy.

Carew added: "This financing round reflects strong conviction in the opportunity to build better financial tools for Canadians and deliver meaningful rewards on everyday spending."

Investor Backing

Khosla Ventures said the investment reflects confidence in both Chexy's founders and the size of the market for consumer payment products built around everyday expenses rather than discretionary purchases.

"Khosla Ventures backs great founders determined to deliver breakthrough value to consumers by reinventing entire industries. Keith Rabois, myself and our partners believe Liza and Chexy are poised to do just that," said David Weiden, managing director at Khosla Ventures.

Air Canada's continued support highlights the commercial importance of extending loyalty schemes beyond flights and travel spending into more routine parts of household finance.

Through Aeroplan, the airline has already linked its programme to sectors including banking and retail. Chexy gives it another route into recurring spending categories that account for a large share of monthly budgets.

Households And SMEs

Chexy says its users broadly fall into two groups: customers trying to offset living costs through cashback and savings, and those aiming to maximise travel and loyalty points. The company argues both are drawn to the same core proposition: earning something back on spending that cannot easily be avoided.

Its expansion beyond rent also broadens the addressable market. In addition to utilities and taxes, Chexy is targeting landlords and property managers that want to offer more modern payment options, while continuing to build out services for smaller businesses.

Over time, the company plans to develop into a broader household finance platform, with tools for paying bills, tracking spending and managing financial decisions. For now, its immediate focus is on adding more payment categories that can generate rewards and increasing loyalty partnerships tied to essential spending.