Payment Operations & Compliance Specialist

Chexy Co.; Toronto; On-site; CAD 65,000 - 85,000; Full time

Job summary

A fintech company in Toronto is seeking a detail-obsessed Payment Operations & Compliance Specialist to manage the integrity of financial operations. The role involves daily reconciliation of payment systems, acting as an escalation point for issues, and ensuring compliance with regulatory frameworks. Ideal candidates should have 3-5 years of experience in fintech operations and a strong understanding of Canadian payment systems. This full-time position promises involvement in strategic operations and mentorship from industry leaders.

Benefits

Mentorship from industry leaders

High-performance team culture

Opportunities for growth and learning

Qualifications

• 3–5 years in fintech operations or payments operations.
• Strong understanding of Canadian payment systems.
• Familiarity with PCI DSS and SOC 2 frameworks.

Responsibilities

• Own daily reconciliation across all payment rails.
• Act as first-line escalation for payment failures.
• Support compliance framework across FINTRAC and Bank of Canada.

Skills

Detail-oriented

Investigative mindset

SQL proficiency

Job description

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.

Payment Operations & Reconciliation

• Own daily reconciliation across all payment rails (cards, EFT, e-transfer), ensuring FBO/DDA balances, processor reports, and internal ledgers are fully aligned.


• Investigate and resolve payment discrepancies, settlement breaks, and processor-level anomalies with urgency and precision.

Operational Risk & Integrity

• Act as first-line escalation for payment failures, delayed settlements, and payout exceptions, coordinating across engineering, banking partners, and support.


• Maintain operational controls that protect customer funds and ensure accurate, timely movement of money.

Regulatory & Compliance Stewardship

• Support Chexy’s compliance framework across FINTRAC, Bank of Canada (RPAA), and sponsor-bank requirements.


• Assist with regulatory reporting, audits, policy updates, and evidence gathering to ensure audit readiness at all times.

Chargeback & Dispute Strategy

• Own the end-to-end chargeback lifecycle across card networks.


• Develop data-driven playbooks to improve win rates, reduce fraud exposure, and strengthen evidentiary standards in disputes.

IT & Security Compliance (NEW – scoped appropriately)

• Partner with engineering and security teams to support compliance with PCI DSS, SOC 2, and internal security controls.


• Assist with evidence collection, control testing, and remediation tracking for IT and security audits (e.g., access controls, logging, incident response).


• Ensure operational processes align with security requirements (e.g., least privilege, data handling, vendor access).

Technical & Process Evolution

• Use SQL to investigate data issues, reconcile discrepancies, and support compliance analysis.


• Drive automation and tooling improvements (including AI-assisted workflows) to reduce manual effort and operational risk.

Qualifications

Experience

• 3–5 years in fintech operations, payments operations, banking operations, or compliance-heavy roles within financial services.

Payments & Regulatory Knowledge

• Strong understanding of Canadian payment systems (cards, EFT, FBO structures).


• Working knowledge of FINTRAC and Bank of Canada (RPAA) expectations.

IT / Security Compliance Exposure (NEW)

• Familiarity with PCI DSS and SOC 2 frameworks (hands-on audit experience not required, but exposure is).


• Experience supporting audits, gathering evidence, or working cross-functionally with security/engineering teams.


• Understanding of basic security concepts: access controls, logging, incident response, vendor risk.

Operational Rigor

• Extremely detail-oriented; comfortable with reconciliations, deadlines, and high accountability.


• Strong investigative mindset — you trace issues to root cause, not just symptoms.

Technical Curiosity

• Comfortable working with data (SQL proficiency preferred).


• Curious about automation, tooling, and scalable systems.

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.