Senior Developer Support Engineer (Agentic Ops & AI)

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, support is an engineering discipline. Our customers are developers building the future of software, and they deserve answers that go deeper than a knowledge base link. We are redefining the standard of technical support by combining deep human expertise with advanced AI agents. We need you to not just solve complex technical issues, but to architect the systems that help us scale that expertise to millions of developers.

Sentry Support Engineers don't just clear queues; they are orchestrators. You will engage with our users across GitHub, Discord, and our support systems, while also acting as the product owner for our AI Agents. You ensure that when a developer asks a complex question, our AI has the right context, the right data, and a seamless "Human-in-the-Loop" path to you when deep expertise is required.

We’re looking for a coder who is passionate about both customer experience and the cutting edge of Agentic Operations. You will drive success by scaling our support through AI, while personally stepping in as a strategic consultant for the most nuanced architectural challenges.

In this role you will

Master the Sentry Ecosystem

• Become a Platform Expert: Develop deep authority on Sentry’s features to guide customers through complex debugging workflows.

• Resolve Technical Inquiries: Answer inbound support requests with a focus on teaching and enabling developers, not just closing tickets.

• Troubleshoot SDK Implementations: Go beyond the UI to help developers instrument Sentry’s SDKs within their specific codebases and frameworks.

• Manage Bugs & Escalations: Triage and reproduce product bugs, serving as the bridge between customers and our Engineering teams.

Pioneer AI-First Support

• Train our AI Agents: Manage the performance of our support bots (Triage, Billing, and Technical), ensuring they provide accurate, high-quality assistance.

• Curate "AI-Ready" Knowledge: Write and structure documentation specifically optimized for RAG (Retrieval-Augmented Generation), ensuring our AI can easily find and use the right information.

• Design Human-in-the-Loop Flows: Define the logic for when an AI should hand off to a human, ensuring context is preserved so customers never have to repeat themselves.

• Monitor & Refine: Review AI responses for accuracy or hallucinations, creating examples of "perfect answers" to continuously fine-tune the model’s performance.

• Handle Complex "Edge Cases": Step in as the expert "Solutions Architect" for gray-area technical issues where AI reaches its limit.

• Drive Automation Strategy: Focus on solving problems at the source—building systems and content that resolve issues before a human ever needs to intervene.

You’ll love this job if you

• You’re an AI-First Tinkerer: You believe things should "just work," and you’re excited to use MCP (Model Context Protocol) to connect AI agents to our internal tools.

• You Value Evidence-Based Support: You prefer looking at data trends over anecdotal evidence.