Technical Support Engineer

About the Role

Sentry is a leader in application monitoring, trusted by over 200,000 organizations worldwide. Our technical support team is at the forefront of this effort, providing strategic consulting services to senior engineers at our largest enterprise customers. As a Technical Support Engineer, you will be responsible for mastering the Sentry ecosystem, performing root-cause analysis, and troubleshooting SDK implementations.

The role is based in Toronto, Ontario, Canada, and offers the opportunity to work remotely. You will engage with users across GitHub, Discord, and our internal systems, acting as a Technical Lead for our Agentic Ops. Your expertise will ensure that when a developer asks a complex question, our systems have the right context and a seamless "Human-in-the-Loop" path to you when deep, nuanced expertise is required.

What You Will Do

• Master the Sentry Ecosystem & Support Elite Developers: Deep-Dive Debugging, Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments
• Support the Great Minds: Act as a strategic consultant for senior engineers at our largest enterprise customers, solving high-stakes architectural challenges that push the boundaries of observability
• Troubleshoot SDK Implementations: Go deep into the source code of Sentry’s SDKs to help developers instrument complex frameworks and custom environments
• Engineer Agentic Operations (The Scaling Engine): Engineer the logic that powers our support agents, moving beyond probabilistic guesses to high-fidelity, autonomous resolutions
• Knowledge Engineering: Build the right context into our systems so they can resolve issues consistently and indefinitely
• Agentic Tooling Development: Use MCP (Model Context Protocol) and Sentry’s internal APIs to build "skills" for our agents, allowing them to perform complex lookups or state-checks autonomously
• The Seer Philosophy: Apply the same philosophy to the support lifecycle—moving us from a "Help Desk" to an "Autonomous Resolution Engine"
• Serve as the bridge between the world's best developers and our product teams, using data from your systems to prioritize high-impact platform fixes
• Collaborate with cross-functional teams to develop and implement automated resolution paths
• Develop and maintain technical documentation and knowledge bases

What We Are Looking For

• 4+ years of experience in technical support engineering, systems engineering, or software development, with a track record of solving high-complexity SaaS problems
• Strong Coding Foundations: Mastery of Python, JavaScript, Java, or Ruby
• Systems Depth: Deep understanding of distributed systems, microservices, APIs, and the "path of a pixel" from frontend to backend
• Experience with automation tools and technologies, such as MCP and internal APIs
• Strong analytical and problem-solving skills, with the ability to debug complex issues
• Excellent communication skills, with the ability to act as a strategic consultant for senior engineers
• Experience working with GitHub, Discord, and other collaboration tools
• Ability to work in a fast-paced environment, with a focus on innovation and experimentation

Nice to Have

• Experience with AI-native systems and autonomous agentic systems
• Knowledge of DevOps practices and tools, such as CI/CD pipelines and containerization
• Experience with cloud-based infrastructure and platforms, such as AWS or Azure
• Familiarity with Sentry’s products and services, including Sentry’s SDKs and APIs

Benefits and Perks

• Competitive salary and benefits package
• Opportunity to work remotely, with a flexible and autonomous work environment
• Professional development opportunities, including training and education programs
• Access to cutting-edge technologies and tools, including AI-native systems and autonomous agentic systems
• Collaborative and dynamic work environment, with a focus on innovation and experimentation
• Recognition and rewards for outstanding performance, including bonuses and stock options
• Comprehensive health and wellness program, including mental health support and employee assistance programs
• Flexible PTO and vacation policy, with a focus on work-life balance

• Develop a strong portfolio that showcases your technical skills and experience, including examples of complex issues you've resolved and automated resolution paths you've developed
• Prepare to showcase your coding foundations, including your proficiency in languages such as Python, JavaScript, and Ruby
• Research Sentry's products and services, including their SDKs and APIs, to demonstrate your knowledge and interest in the company
• Highlight your experience working with automation tools and technologies, such as MCP and internal APIs
• Be prepared to discuss your approach to problem-solving and debugging complex issues, including your use of data and analytics to inform your decisions
• Show your passion for innovation and experimentation, and your ability to work in a fast-paced environment with a focus on autonomy and self-directed work
• Don't be afraid to ask questions during the interview process, including about the company culture and values, as well as the opportunities for growth and professional development