Chexy raises $14 million Series A led by Khosla Ventures

Chexy has raised a $14-million CAD Series A round to fund its expansion from helping tenants earn credit card rewards into supporting more everyday expenses, including business payments.

The round was led by Khosla Ventures, one of Silicon Valley’s most reputable venture firms, which has backed giant tech companies like OpenAI, DoorDash, Stripe, and Instacart. Returning investors such as Crossbeam, Venrex, and Air Canada, which partnered with Chexy for its Aeroplan program, also participated in the round.

Chexy remains Canadian-controlled, with no immediate plans to expand into or serve the US market.

Launched in 2023, Chexy initially focused solely on helping tenants earn credit card rewards through rent payments. The company pays bills and rent on consumers’ behalf, while the consumer pays Chexy with a credit card. This means consumers get points or cash back to use on rewards like vacations or other luxuries by simply paying the bills.

Chexy said in a statement that it will use its latest funding to scale its payments platform across Canada, expand its partnership ecosystem, and grow its team. The company said it’s aiming to “become a financial hub for households”—a platform for Canadians to pay bills and track spending.

Chexy has also found a “huge opportunity” in the small-to-medium-sized business (SMB) market, where the company said businesses are turning to its platform to manage payroll, business taxes, and vendor payments. SMB demand came “naturally” following Chexy’s Aeroplan partnership, co-founder and CEO Liza Akhvledziani Carew told BetaKit in an email statement. She added that the company is scaling its product capability for SMBs over the coming months.

SMBs “see Chexy as a great way to digitize payments, extend cash flow, and earn rewards on business payments,” Akhvledziani Carew said. “This was a surprise to us, but we see this as a huge opportunity now.”

While Canadian tech startups often face pressure to relocate to the United States to secure investment from deep-pocketed Silicon Valley investors, Chexy said it remains Canadian-controlled and headquartered in Toronto, with no immediate plans to expand into or serve the US market. In a statement, Khosla Ventures founding partner David Weiden said he believes Chexy is “poised” to reinvent the industry.

Chexy last raised $4.1 million in 2024 to build out payments infrastructure to support more household services beyond rent. At that point, Chexy had 16 employees and processed more than $10 million in rent every month. Akhvledziani Carew said that Chexy is now processing over $1 billion in annualized payment volume, and is on track to process over $2 billion in payments next month.

Chexy said it serves more than 200,000 users nationwide who have earned over $35 million in rewards and cash back value since it launched.

Akhvledziani Carew said Chexy has added 10 employees across its growth, product, engineering, and operations teams in downtown Toronto over the past month, bringing its total headcount to 32 employees. She added that she anticipates hiring another five to 10 team members over the next year, primarily within its operations team.

Feature image courtesy Chexy.