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Sentry Logo Sentry · IT - Administration

Manager, Technical Support

Canada, Toronto 160000.00 - 180000.00 CAD / Year · Job Posted January 22, 2026
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Job Description

At Sentry, our customers are software developers. Solving their problems is complex, technical, and requires deep code literacy. We don't believe in 'managers who don't know the product.' We are looking for a Technical Support Manager who leads from the front lines. You will lead a team of high-performing Support Engineers, but you won't be managing from an ivory tower. You will be a 'Player-Coach' - spending a significant portion of your week in the queue, handling the most complex technical escalations, debugging code in open-source repos, chatting with engineers at Discord, and acting as the primary Subject Matter Expert (SME) for your team. You are a former engineer or high-level support architect who loves the technical hunt but is ready to force-multiply that passion by mentoring a team. You will drive success not just by tracking metrics, but by showing your team how to solve the unsolvable.

Job Responsibility

  • Lead from the Front (Technical Execution): Be the Technical SME: Serve as the ultimate escalation point for complex questions regarding Sentry’s SDKs, trace propagation, and more
  • Active Queue Participation: Dedicate a portion of your week to answering inbound support requests, keeping your product knowledge sharp and setting the standard for quality
  • Triage & Debug: Triage, reproduce, and report complex product bugs. You will be expected to read source code to distinguish between a user error and a true platform bug before escalating to Engineering
  • Community Engagement: Engage directly with users in our public channels (Discord, GitHub) to solve problems and represent the Sentry brand technically
  • Manage & Mentor (Team Leadership): Develop the Team: Conduct code reviews on ticket responses, provide deep technical feedback, and mentor engineers on debugging strategies and software fundamentals
  • Drive Performance: Own your team’s core metrics (CSAT, Response Time, Resolution Time) and workload balancing
  • Shape the Knowledge Base: Not only write articles yourself but curate the team's output to ensure our internal guides and customer-facing docs are technically accurate and up-to-date
  • Incident Command: Participate in the on-call rotation for high-severity issues and act as the Incident Commander for support during critical outages.

Requirements

  • 8+ years of total experience in technical support, software engineering, or sales engineering
  • 2+ years of people management or team lead experience, with a track record of hiring and mentoring technical talent
  • Deep Technical Proficiency: You must be able to read and debug code. Experience with Python, JavaScript, or other languages is required. You should be comfortable opening a browser console or a terminal to reproduce an issue
  • Modern Stack Knowledge: Strong understanding of the modern dev landscape (CI/CD, APIs, Microservices, Frontend vs. Backend, Observability)
  • Hands-On Philosophy: A willingness to roll up your sleeves and work tickets. If you are looking to move away from technical work entirely, this is not the role for you.

Nice to have

  • Previous experience working as a Software Engineer or in a DevOps role
  • Active contributions to Open Source projects (please share your GitHub!)
  • Experience implementing Support tools or workflows (Zendesk, JIRA, Linear).

What we offer

  • incentive compensation
  • equity grants
  • paid time off
  • group health insurance coverage
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