Payment Operations & Compliance Specialist
Chexy
Operations, Compliance / Regulatory
United States · Toronto, ON, Canada
Posted on Jan 20, 2026
At Chexy, we’re reshaping the way money moves - making payments smarter, faster, and more rewarding.
We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we’re on a much bigger mission: to build a super app that acts as your co-pilot for all your money—helping you get more value from every dollar you spend.
As a high-growth fintech startup, we’re at the forefront of payments innovation, and we’re looking for hungry, ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we’d love to work with you.
The Role
We’re looking for a detail-obsessed, high-ownership Payment Operations & Compliance Specialist to serve as the "Financial Detective" and "Source of Truth" for Chexy. In this role, you will own the end-to-end integrity of our financial plumbing, managing the daily pulse of our FBO and DDA accounts to ensure every dollar is perfectly accounted for.
As a unique hybrid of operations lead and regulatory steward, you will build the "playbooks" for our chargeback strategy and revenue protection while ensuring we remain a gold standard for FINTRAC and Bank of Canada compliance. This is a full-time, in-office position (5 days a week) where you’ll work side-by-side with our senior leadership team to master the "how" behind a scaling fintech. You will be the bridge between complex financial movement and a seamless customer experience, ensuring our ledgers remain balanced while we build the future of rent payments.
Key Responsibilities
- Payment Reconciliation: Perform daily reconciliation of our float balances. You will track the movement of money across all payment rails, ensuring bank balances, daily ledgers, and internal records are in perfect synchronization.
- Operational Integrity: Act as the first line of defense for payment failures. Whether the issue is technical, operational, or a banking "glitch," you will identify the discrepancy and coordinate with the team to resolve it immediately.
- Compliance Subject Matter Expert: Support our compliance framework by staying up-to-date with FINTRAC and Bank of Canada (RPAA) requirements. You will help ensure our reporting is flawless and our policies are audit-ready.
- Chargeback Innovation: Bring a fresh, data-driven approach to our chargeback management. You will handle the dispute lifecycle while actively looking for innovative ways to increase our win rates and decrease fraud-related losses.
- Technical Evolution: While this role deals with financial records, we are a tech-first company. You will use SQL to investigate data and be expected to learn and adopt new automation tools (including AI-driven processes) to move us away from manual spreadsheets.
Qualifications
- Experience: 2–4 years in Fintech Operations, Bank Reconciliation, or a Compliance-heavy role.
- Knowledge Base: A solid understanding of Canadian financial regulations and payment systems (EFT, Credit Card rails, FBO structures).
- The "Tedious" Mastery: You find satisfaction in a balanced ledger. You have the patience for hectic month-end closes and the precision to find a single missing cent.
- Technical Curiosity: Proficiency in SQL (or a strong willingness to learn it within your first 3 months). You understand that the future of finance is technical and are eager to grow your skills.
- Problem Solver: You don’t just report a problem; you investigate the "why" and suggest a structural fix.
- Payments Ecosystem Experience (Nice to Have): Hands-on experience working with payment processors, acquiring banks, card networks, or issuing banks—particularly in areas such as settlement, disputes, or reconciliation.
Why Join Chexy?
- Mentorship from the Best: You’ll be a core member of our analytics and operations team, working directly with leaders who live and breathe fintech. It’s a front-row seat to building a category-defining company.
- Strategic Impact: You are the guardian of our capital. Your oversight ensures the financial health and regulatory safety of thousands of tenants across Canada.
- The "Chexy" Vibe: We’re a high-performance team that actually likes each other. Expect a culture where we debate SQL optimization and payment logic with the same passion we use to pick a lunch spot. We are fast, ambitious, and have zero tolerance for "corporate boredom."
- Work with the "Extra-Talented": You’ll be part of a team that is genuinely obsessed with fintech. If you want to be around people who are smarter than you (in a good way) and can teach you something new every single day, this is the place.
- Sassy & Serious: We take the money very seriously, but we don't take ourselves too seriously. We move fast, we laugh a lot, and we never let "that’s how it’s always been done" get in the way of a better idea.