Staff Software Engineer, AI Developer Tooling

About the role

This position sits within the Platform Engineering organization to lead the development of AI-assisted coding workflows across the entire company. You will transform internal systems into agent-ready platforms, enabling tools like Claude Code to interact with our infrastructure programmatically. This role focuses on the full lifecycle of AI engineering, from context management and harness design to automated pull request generation and system guardrails.

Key facts

What you'll do

• Audit existing internal developer systems to identify gaps and prioritize the creation of APIs that support end-to-end AI agent functionality.
• Develop the harness, feedback loops, and context engineering systems required for agents to produce high-quality, repository-aware pull requests.
• Automate routine engineering tasks such as security dependency updates, minor bug fixes, and general maintenance.
• Design internal tools including productivity dashboards, automated issue triage, and CI/CD optimizations to reduce developer toil.
• Identify organizational bottlenecks through data analysis and direct observation, then secure cross-team buy-in to implement solutions.

Requirements

• 10+ years of professional software engineering experience.
• Demonstrated background in building developer tools, CI/CD pipelines, or AI-first coding workflows.
• Strong foundation in software and system design.
• Hands-on experience with AI coding tools and agents.
• Ability to communicate complex technical strategies to senior leadership.
• Proven track record of leading and completing cross-team technical initiatives.

Nice to have

• Experience working with large-scale distributed systems or monolith decomposition.
• Prior involvement in engineering productivity or developer experience programs.
• Familiarity with static analysis, code review tooling, or automated PR pipelines.

Skills & tools

• AI coding agents
• API development
• CI/CD infrastructure
• System architecture
• Developer tooling
• Context engineering

Practical notes

• Compensation includes eligibility for employee benefit plans, including group health insurance and paid time off.
• Sentry provides reasonable accommodations for candidates with disabilities during the application process; contact accommodations@sentry.io for assistance.