Technical Support Engineer

2 weeks ago

Berkeley Street Suite Toronto Ontario Canada MA J Open Career Full time
Technical Support Engineer
At Chexy, we're reimagining how Canadians manage their largest expenses—like rent, tuition, and insurance—by transforming them 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 $1B+ in annual payment volume and millions of transactions per month, we're processing real money for real people—which means when something goes wrong, it needs to be handled quickly, accurately, and with care.
About the Role
We're looking for a Technical Support Engineer to sit at the intersection of our Engineering and Customer Experience teams. You'll be the critical bridge between users experiencing issues and the engineers building solutions—triaging bugs, investigating payment anomalies, writing detailed technical tickets, and resolving issues when possible.
This is a hybrid role that requires both technical chops and exceptional communication skills. You'll need to understand our payment systems well enough to debug issues, while being organized enough to manage multiple support channels and ensure nothing falls through the cracks. If you're someone who loves solving problems, thrives on organization, and wants to work at the intersection of product, engineering, and customer success, this role is for you.
What You'll Be Doing
  • Manage and respond to technical support inquiries through Intercom, our customer support platform
  • Investigate and triage technical bugs reported by users or the CX team, determining severity and priority
  • Write clear, detailed tickets for engineering with reproduction steps, user impact, and relevant data
  • Track bug statuses and communicate updates back to CX and affected users
  • Investigate payment anomalies including failed transactions, ledger discrepancies, and settlement issues
  • Resolve technical issues directly when possible, including data corrections, configuration fixes, and user account issues
  • Write and maintain internal documentation and runbooks for common issues and resolution steps
  • Coordinate between Engineering, CX, and Product teams to ensure timely issue resolution
  • Monitor support metrics and identify patterns that indicate larger systemic issues
  • Participate in incident response for production issues affecting payments or user accounts
  • Build internal tools and scripts to automate common support tasks and improve efficiency
  • Provide technical training and support to the CX team on product features and troubleshooting

Who We're Looking For
  • 1-2 years of experience in technical support, customer support, or engineering (new graduates with relevant internships or co-op experience are welcome)
  • Strong technical aptitude with ability to understand APIs, databases, and payment systems
  • Experience with at least one programming language (TypeScript, Python, JavaScript, or similar) and comfort reading and writing code
  • Exceptional organizational skills with ability to manage multiple priorities and track issues without dropping anything
  • Outstanding written and verbal communication skills—you can explain technical concepts to non-technical audiences and vice versa
  • Strong attention to detail, especially when investigating financial transactions and data accuracy
  • Experience with customer support tools (Intercom experience is a plus)
  • Ability to work under pressure when dealing with time-sensitive payment issues
  • Self-directed with ability to prioritize and make decisions independently
  • Empathy for users and commitment to delivering excellent support experiences
  • Comfort with ambiguity and ability to figure things out when documentation is incomplete

Bonus Points
  • Experience in fintech, payments, or financial services support
  • Familiarity with SQL for querying databases to investigate issues
  • Understanding of REST APIs and how to test/debug API calls
  • Experience writing technical documentation or runbooks
  • Background in QA, testing, or bug triage
  • Familiarity with , TypeScript, or NestJS
  • Experience with ticketing systems like Jira, Linear, or similar
  • Understanding of payment systems, ledgers, or financial transactions
  • Experience building internal tools or automation scripts
  • Previous experience working cross-functionally between technical and non-technical teams

Why Join Chexy?
Solve problems that matter: Your work directly impacts users experiencing real financial issues—your diligence and speed can make someone's day Join a tight-knit team: Work directly with Engineering, CX, and Product teams with visibility across the entire company Early equity: Access equity in a high-growth fintech company that's just getting started Learn fast: Gain deep exposure to payment systems, production engineering, and fintech operations Toronto office: Work in-office 5 days a week with the team in Toronto
How We Hire
We keep our hiring process clear and human. You'll go through conversational interviews and a lightweight technical assessment to showcase your problem-solving and communication skills. We care about how you think, how you organize your work, and how you communicate—not just what you know. And we make sure there's space for your questions too.

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