Senior Backend Engineer at Chexy in Toronto

At Chexy, we're building modern financial tools for Canadians - starting with their largest expenses. We turn rent, tuition, insurance, and other big bills into opportunities to build credit, earn rewards, and gain financial flexibility.

We're the first platform in Canada that lets users pay nearly any bill using their credit card, while unlocking meaningful benefits like cashback, points, and credit-building tools. With ~$2B in annual payment volume and hundreds of thousands of transactions a month, we're building financial infrastructure that needs to be fast, reliable, and bulletproof.

About the Role

We're looking for a Senior Backend Engineer to own a payments domain in Chexy's core backend service end to end. You'll work on the systems that move money - inflows, outflows, ledgering, settlement, and direct integrations with card networks and banking systems - and you'll be the person who decides how they're built.

This is an ownership role. You'll set the architecture and the reliability bar for your domain, you'll be trusted to make calls without waiting to be told, and you'll help the engineers around you get better. The problems in front of us are the ones you don't get to work on at most companies: a chequing product, card issuance, instant payouts, and a ledger rebuild.

What You'll Be Doing

• Own a payout or pay-in rail end to end - architecture, reliability, observability, and roadmap
• Lead design on our ledger: double-entry correctness, reconciliation against processors and banks, settlement timing, auditability
• Build and harden direct integrations with payment networks and Canadian banking rails
• Design durable, event-driven workflows (Google Cloud Pub/Sub, Temporal) so money movement is idempotent, recoverable, and never double-sent
• Set the technical bar: review architecture, write the patterns others follow, and push back when something isn't safe
• Define what "reliable" means for your domain - SLOs, alerts, runbooks - and make it true
• Mentor engineers through reviews and pairing, and help them level up
• Work directly with the CTO on what we build next and in what order

What Senior Means Here

• You make trade-off calls without waiting to be told, and you're right most of the time
• You surface problems early and specifically - before they hit users or the books
• You disagree openly, then commit fully
• You multiply the team - patterns, reviews, mentoring - rather than only shipping your own work
• You own outcomes, not tasks. If your domain is broken, that's yours to fix, not someone else's to notice

Who We're Looking For

• Substantial backend experience with TypeScript/Node in production, including systems where correctness actually mattered - payments, ledgers, billing, or similar
• Deep understanding of relational databases: schema design, transactions, isolation levels, and what breaks under concurrency
• You've built or operated event-driven systems and know the failure modes - duplicate delivery, out-of-order, poison messages
• Fluent in financial systems concepts: double-entry, reconciliation, idempotency, settlement
• You already build with AI coding tools every day and have strong opinions about where they fail
• You've owned something before - a service, a domain, an integration - through incidents and all
• You've been early somewhere and liked it - you're comfortable making decisions with 70% of the information and revisiting them when the picture changes
• You communicate clearly in writing and don't need a manager to tell you what matters

Bonus Points

• Direct experience with card networks or Canadian banking APIs
• Rust, or interest in taking a ledger to Rust/TigerBeetle - we're exploring this for our next ledger
• Google Cloud Platform, Terraform, Temporal
• Background in regulated or compliance-heavy environments

How We Build

We're early. The roadmap moves as we learn from users, partners, and regulators - sometimes week to week - and you'll regularly pick things up outside your title. The people who do best here find that energizing. They'd rather make a call with most of the information than wait for all of it, they get curious instead of frustrated when a requirement changes halfway through, and they've usually been early somewhere before and wanted to do it again.

The way software gets built is changing faster than anyone's best practices can keep up, and we're not pretending otherwise. Most of what we ship is written with AI tools - but that's the least interesting part. The interesting part is working out what that means for how we review, test, and take responsibility for code: what you hand to a model and what you never do, what "I read the diff" means when the diff is two thousand lines, how a small team keeps quality up while moving faster than it should be able to. We're writing that playbook as we go, and we want people who want to write it with us, not people waiting to be handed it. We care a lot about attitude - someone who brings energy into a room rather than absorbing it. When something breaks, they're already on it before anyone asks.

Why Join Chexy?

💥 Build payments infrastructure that matters: Your code moves ~$2B a year for tens of thousands of Canadians
🤖 Work the way engineering works now: AI-native tooling, category-defining technology, and end-to-end ownership
💬 Join a tight-knit team: Work directly with the founders and CTO, who trust you to make real decisions
📈 Early equity: Access equity in a high-growth fintech
📍 Toronto office: We work in-office 5 days a week

How We Hire

We keep our hiring process clear and human. You'll go through a mix of conversational interviews and technical deep-dives designed to show how you think, how you've solved real problems, and how you work with others.

We use AI tools to help us organize and review applications; every decision about who we interview and who we hire is made by a person. This posting is for an existing vacancy. If you interview with us, we'll let you know within days of your last interview whether a decision has been made.

Chexy is an equal opportunity employer. If you require any accommodations or support during the hiring process, let us know and we'll do our best to help.
Know someone who would be a perfect fit? Let them know!