Toronto-based fintech Chexy announced it secured $14 million in Series A financing, allowing the firm to further transform how Canadians pay recurring and large expenses, and earn rewards while doing so.

This Series A financing round was led by Khosla Ventures, a Silicon Valley venture firm that has backed OpenAI, DoorDash, Stripe and Instacart. The financing also included support from Air Canada.

The platform lets Canadians pay large recurring obligations — including rent, utilities, government taxes and vendor payments with a credit card, unlocking travel rewards or cashback on payments that traditionally do not qualify.

Co-founder and CEO Liza Akhvledziani Carew said the idea for Chexy came from the frustration she had in paying rent on an apartment in Toronto. She had just moved to the city while working for Square Canada and found that paying monthly rent was still done by paper, post-dated checks. 

“Here I am working for one of the fastest growing digital payments companies in the world, but my largest and most painful expense is still done by this kind of method.” she said in an interview with TechNX. 

Earning rewards on recurring, large payments

Chexy launched in 2023 having secured early backing from such venture capital funders as Antler, a global accelerator for zero-day founders of some $150,000 and later $1.3 million from New York-based Gallery Ventures.

The idea behind Chexy is simple. Allow Canadians to pay such things as rent with a credit card, even if a landlord does not accept credit card payments. Chexy lets a user use their credit card and when it comes time to pay the monthly rent, charges the credit card, then pays the landlord by their preferred method, Interact e-transfer or bill pay.

Since it launched, the number of users of Chexy has grown rapidly. It is now used by over 200,000 Canadians, according to the company.

“We were getting so much demand not just from renters, but from Canadians wanting to pay for all kinds of things through Chexy: childcare, utilities, property taxes, you name it,” Akhvledziani Carew added.

By expanding what recurring bills can be paid with Chexy, it allowed users to earn reward points on those transactions with their credit cards that were not possible before. 

“Before Chexy, an entire category of (reward) earning simply didn’t exist,” she continued. “Thousands of dollars in essential payments generated zero rewards. Chexy changes that.”

This soon caught the eye of Aeroplan, one of Canada’s largest travel loyalty programs with some nine million active members. Chexy and Aeroplan launched a rewards integration program last April letting Aeroplan members earn bonus points on large recurring payments made through Chexy.

“It’s not dissimilar to the partnerships Aeroplan has with Uber and Starbucks, or with the LCBO where you earn bonus points for buying a bottle of wine,” Akhvledziani Carew said.

“Chexy is defining a category that didn't exist before, making rewards a reality on the payments that matter most in Canadians' everyday lives. As that mission scales, so does the opportunity for our members, and we're so proud to be a partner at the centre of it,” Scott O’Leary, vice-president, loyalty and product at Air Canada, said in the press release announcing the Chexy new round of financing.

Staying in Canada as a fintech

Akhvledziani Carew said this new round of financing will be used to expand Chexy’s engineering and product teams, accelerate marketing and build new and deepen existing partnerships with payment operators and loyalty programs.

She said the firm has no plans to move to the United States, as some other fintech startups have done in the past. “We built Chexy to help Canadians get more out of the payments they already have to make.”

Starting a fintech company in Canada has its challenges, Akhvledziani Carew admitted.

“The regulatory side is certainly a big hurdle,” she continued. ”You need to be a money services business, registered with FINTRAC and now also registered with the Bank of Canada under the Retails Payment Activities Act.”

Having overcome those challenges has in many ways made the company more nimble and even better positioned to continue to succeed going forward, she said.