Every bill earns rewards
Rent, tuition, tax and insurance normally leave a bank account by transfer and earn nothing. On Chexy they go on a credit card instead, and the points and cashback go back to the customer. Chexy also handles payments such as mortgages by bank transfer, and those earn rewards too. Over 200,000 Canadians use it, and Chexy has processed more than $2B in bills and returned $40M in rewards.
That design makes every support question specific to one customer. A customer wants to know where one payment sits, why one charge looks the way it does, or when one set of Aeroplan points will appear. The answer lives in that customer's transaction history, spread across several of Chexy's internal systems.
The month arrives in one week
Chexy's volume is not spread evenly. Half or more of a month's tickets arrive in the first week, when rent is due. Chexy expects support volume to grow roughly tenfold as it scales. The plan is to absorb that growth without growing the support team in step.
Duke Lam, who runs operations at Chexy, described what the first week did to the queue, and why more headcount was not the answer.
We would get flooded on the first week of the month and it'll take us a week or more to clear the backlog, and we get just over a week of breathing before it starts again.
Duke Lam
Head of Business Operations
Starting with what the agent could already reach
Chexy went live in November 2025 on a narrow slice of its queue. The agent, which Chexy named Chester, took identity verification and Aeroplan questions.
Those workflows run on help centre content and a short list of account attributes, so Chexy could launch them without waiting on engineering. On the tickets Chester resolved, average handle time fell from 24 hours to about a minute.
The ceiling on volume
Payments is Chexy's largest ticket category, and the agent could not reach the data it needed to answer those questions.
A payment question needs the customer's transaction record, their account status and their payment schedule, and at Chexy those lived in several internal systems with no single route in. Building that route is engineering work, and at a company growing this fast, engineering time goes to the product first.
Through those months the agent handled about 1,500 tickets a month against inbound of about 6,000. The rest of the volume stayed with the team.
Connecting Chexy's systems
In June 2026 Ben Gigone, Chexy's CTO and cofounder, connected Lorikeet to multiple internal Chexy systems.
The agent can now look up payment records, account status and eligibility during a live conversation.
We connected Lorikeet to Chexy's systems, and that allows us to give Lorikeet access to a lot of our data which we previously didn't have access to.
Ben Gigone
CTO and Cofounder
5x the volume with the same team
With the data reachable, Chexy opened Chester up to its whole inbound queue at the end of July.
The agent's share of inbound moved from about 24% to about 72% that week. Monthly tickets handled by the agent went from about 1,500 to over 7,500, with payment questions included for the first time. The support team stayed the same size.
What's next
Chester can read a customer's payment data today. The next step is to let customers act on it: change their own payments and manage their own schedule through Chester, without waiting for the team.
Each new capability builds on the connections Chexy already has to its own systems, rather than adding another integration.
