Technical Support Engineer II

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take ownership of high-complexity escalations from start to finish — troubleshoot, replicate, and drive them to resolution with minimal guidance, even when the way forward is not clearly outlined.

• Act as the incident coordinator during production incidents; restore systems to a steady state, manage communication with stakeholders, and ensure smooth post-incident transitions to the Engineering team.

• Manage technical communications under pressure; set expectations and provide timely, clear updates until the issue is resolved.

• Utilize Cursor as your main AI workspace to triage, diagnose, and resolve issues more efficiently. Conduct log analysis, code exploration, and automation through Cursor agents, while sharing effective prompts, workflows, and patterns with the team.

• Develop lightweight scripts, automations, and macros in Cursor that minimize manual efforts and expedite root cause identification.

• Create dashboards and saved searches across logs, product analytics (Metabase, Pendo), and tickets to identify regressions and emerging trends early — leveraging Cursor to speed up querying, scripting, and synthesis processes.

• Oversee external documentation reviews; assess and approve troubleshooting, runbook, and process documentation to ensure accuracy, testability, and version control for both customer-facing and internal content.

• Contribute to case handoff standards to Engineering, including necessary logs, timelines, and impact assessments.

• Serve as a liaison between TSE, Engineering, and Product — translating recurring customer pain points into prioritized feature requests with clear impact, frequency, and suggested acceptance criteria.

• Lead technical discussions with internal teams regarding complex, multi-system issues.

⛳️ Requirements

• 3–5 years of experience supporting SaaS products with a demonstrated ability to handle complex escalations.

• Bachelor's degree in Computer Science, Engineering, or a related field — or equivalent practical experience.

• Proficient in SQL — including filters, sorting, joins, aggregations, and subqueries — with production or warehouse data.

• Skilled in using REST APIs to replicate issues, validate server responses, and create minimal test cases.

• Experienced with session replay tools (e.g., LogRocket, FullStory) to reconstruct user flows and isolate issues related to UX, product, and data.

• Familiarity with version control systems (e.g., git); able to navigate repositories and interpret diffs comfortably.

• Advanced troubleshooting skills across client, network, API, and data layers utilizing logs, traces, and evidence-based reasoning.

• Comfortable with basic scripting to parse logs, automate reproductions, or generate diagnostics.

🏝️ Benefits

• 💵 Salary – $80,000 - $90,000 CAD. Your base salary compensation will be determined based on factors such as skills, education, experience, and geographic location.

• 🏝️ Paid Time Off

• Canada: Everyone receives 4 weeks of paid leave plus 11 public holidays, along with an 'end of year shutdown' providing an additional 2-week company holiday. You are also entitled to generous paid sick leave.

• 🌴 Work remotely – We are a remote-first company — you can live and work wherever you feel happiest. We also provide a monthly stipend for co-working (in case you want to get out of the house 😉)

• 🤷 Training – We will support you in learning new skills or cover costs for conference or course tickets.

• ❤️ Health Coverage & Retirement – Canada: We offer comprehensive medical, dental, vision, disability, and life insurance coverage, along with a 4% match on Retirement.