Manager, Technical Support

Sentry
Toronto, Ontario, Canada$160k – $180kPosted 7 April 2026

Job Description

Manager, Technical Support ABOUT SENTRY Bad software is everywhere, and we’re tired of it. Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology. With more than $217 million in funding and 100,000+ organizations that believe we’re on to something, we're building performance and error monitoring tools that help companies like Disney, Microsoft, and Atlassian spend less time fixing bugs and more time building products. Sentry embraces a hybrid work model across our global hubs, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration. If you like to selfishly build things that make your digital life better, come help us build the next generation of software monitoring tools. About the Role 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. In this role you will 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. You’ll love this job if - You are a "Tinkerer-in-Chief": You love leadership, but you miss the thrill of fixing a broken build or finding a needle-in-a-haystack bug. - You lead by doing: You believe the best way to earn a team's respect is to be the person they turn to when they are technically stuck. - You are obsessed with "The Why": You don't just want your team to close tickets; you want them to understand the underlying architecture of why the error happened. - You thrive in the deep end: You are comfortable reading stack traces in languages you might not write fluently, and you can explain complex technical concepts to both junior devs and CTOs. Qualifications - 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 me ... (truncated, view full listing at source)
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