Staff Software Engineer, AI Developer Tooling

Sentry4 days ago

Location

San Francisco, California

Type

Full Time

Salary

USD 240,000 – 320,000

Level

Staff

Role

Staff Software Engineer

Posted

Jul 10, 2026

Full TimeStaff

The role

Summary

Staff Software Engineer, AI Developer Tooling at Sentry focuses on building infrastructure and tools that enable AI coding agents to operate effectively within Sentry's development lifecycle. This Platform Engineering role involves auditing internal systems for API accessibility, creating harness tooling and context systems for high-quality code generation, automating routine engineering work, and removing organizational friction across the engineering organization. The ideal candidate has 10+ years of software engineering experience with expertise in developer infrastructure, CI/CD systems, or AI-assisted workflows, combined with strong system design fundamentals and cross-team communication skills.

What you'll do

API Infrastructure Audit and Exposure: Conduct comprehensive audits of Sentry's internal developer systems to identify gaps in API accessibility for AI agents. Prioritize and drive the programmatic exposure of internal systems, building end-to-end connections that enable AI tools like Claude Code to operate directly on engineering infrastructure without requiring human UI interaction.

AI Agent Harness and Context System Development: Design and build harness tooling, context engineering systems, and feedback loops that enable AI agents to generate high-quality, repository-aware pull requests. Implement automated pre-review checks, PR quality measurement systems tailored to Sentry's codebase, and intelligent guardrails that ensure code reliability and organizational standards compliance.

Engineering Work Automation: Identify and automate high-volume, low-priority engineering tasks including security dependency upgrades, minor bug fixes, and routine maintenance tasks. Enable Sentry engineers to redirect focus from toil-heavy work toward higher-value architectural and feature development initiatives.

Developer Experience and Productivity Tooling: Design and build internal tools and systems that measurably improve engineering effectiveness across the organization. This includes productivity dashboards, AI-assisted issue triage platforms, CI/CD pipeline optimizations, and tooling that reduces development friction and accelerates time-to-deployment.

Organizational Friction Identification and Resolution: Use data analysis and direct observation to identify systemic bottlenecks and friction points in the engineering organization. Develop data-backed recommendations for leadership, build cross-team consensus for changes, and drive adoption of improvements that enhance overall engineering velocity and satisfaction.

What we look for

Technical

Software and System Design FundamentalsDemonstrated mastery of designing scalable, maintainable systems with clear abstractions, API contracts, and architectural patterns. Ability to think through complex system interactions, trade-offs between performance and maintainability, and long-term implications of design decisions.

Developer Infrastructure and Platform EngineeringProven experience building, maintaining, or designing developer infrastructure systems, including API servers, service mesh architecture, or platform abstractions that enable other engineers to build efficiently. Understanding of how infrastructure decisions impact developer productivity and build/deployment cycles.

CI/CD and Automation Pipeline ArchitectureHands-on experience designing and implementing continuous integration and deployment pipelines, automated testing frameworks, and deployment automation. Experience with tools and patterns that reduce manual work and improve code quality through automation.

AI Coding Tools and Agent IntegrationGenuine, hands-on familiarity with modern AI coding tools and agents such as Claude, GitHub Copilot, or similar systems. Understanding of how these tools can be integrated into development workflows, their capabilities, limitations, and practical considerations for enterprise adoption.

Large-Scale System ArchitectureExperience working with distributed systems, microservices architectures, monolith decomposition strategies, or high-scale backend systems. Ability to design systems that handle complexity, maintain reliability under load, and scale across organization-wide initiatives.

Education

Computer Science or Related FieldBachelor's degree in Computer Science, Software Engineering, or equivalent professional experience demonstrating strong fundamentals in algorithms, data structures, system design, and software architecture. Experience demonstrating equivalent depth of technical knowledge is highly valued.

Experience

10+ Years of Software EngineeringSubstantial track record spanning over a decade of building production software systems at scale. Demonstrates comprehensive understanding of software development lifecycle, architectural patterns, and the discipline required to ship reliable systems that impact users and organizations.

Developer Tools or Workflow OptimizationProven experience building tools, frameworks, or workflows that meaningfully improve how developers or AI agents work. This may include CI/CD platform experience, developer infrastructure projects, AI-first coding workflows, or public open-source contributions that enhance developer productivity.

Cross-Team Technical LeadershipTrack record of driving complex technical initiatives across multiple teams and organizational boundaries. Demonstrated ability to influence stakeholders, gather requirements from diverse teams, maintain momentum through ambiguity, and deliver projects that require coordination and buy-in from multiple engineering groups.

Developer Experience and Productivity ProgramsPrior involvement in engineering productivity initiatives, developer experience improvements, or projects aimed at reducing developer toil. Understanding of how to measure productivity improvements, identify high-impact pain points, and implement solutions that resonate with engineering teams.

Code Review and Quality ToolingFamiliarity with code review platforms, static analysis tools, automated PR quality gates, and similar systems that enforce code standards and quality. Understanding of how to integrate automated quality checks into development workflows without creating friction.

Skills

Required skills

System Design and ArchitectureAbility to design large-scale systems with clear separation of concerns, scalability considerations, and maintainability. Skill in defining API contracts, selecting appropriate technologies for different problems, and thinking through failure modes and edge cases.

Backend Software EngineeringCore competency in building robust backend systems and services. Strong understanding of API design, database design, caching strategies, asynchronous processing, and the operational considerations that make systems reliable and performant at scale.

Developer Infrastructure and DevOpsHands-on experience with infrastructure-as-code, containerization, orchestration, CI/CD pipeline design, and deployment automation. Ability to design systems that enable other engineers to build, test, and deploy efficiently.

Python or Go ProgrammingProduction-level proficiency in Python, Go, or similar languages commonly used in infrastructure and backend systems. Ability to write clean, maintainable code at scale and work comfortably with large, complex codebases.

API Design and IntegrationExpertise in designing clean, intuitive APIs that other systems can integrate with. Understanding of REST principles, gRPC, authentication/authorization patterns, versioning strategies, and designing APIs that serve automation and agent-based workflows.

Technical Communication and LeadershipAbility to communicate complex technical concepts clearly in written and verbal form. Skill in presenting technical recommendations to senior leaders, writing detailed design documents, and influencing stakeholders without formal authority.

Nice to have

AI and Machine Learning IntegrationFamiliarity with integrating AI models into production systems, understanding of LLM capabilities and limitations, experience with prompt engineering, RAG systems, or similar AI-native architectures. Understanding of how to design systems that work effectively with AI agents.

Open Source ContributionPublic contributions to open-source projects, particularly those focused on developer tools, infrastructure, or AI-native workflows. Demonstrates initiative, understanding of community-driven development, and passion for building tools that benefit the broader engineering community.

Monolith Decomposition and MigrationHands-on experience breaking down monolithic systems into microservices, managing database migrations, or orchestrating large-scale system refactors. Understanding of strategies for maintaining reliability during significant architectural changes.

Observability and Monitoring SystemsExperience designing or working with monitoring, logging, and observability platforms. Understanding of how to instrument systems effectively, aggregate signals from distributed systems, and use observability data to drive engineering decisions and identify system health.

Performance Optimization and ProfilingExperience profiling production systems, identifying bottlenecks, and implementing performance optimizations. Skill in measuring impact of optimizations and understanding trade-offs between performance, maintainability, and resource utilization.

High-Agency Project OwnershipDemonstrated ability to identify problems independently, structure solutions, and drive initiatives from conception to completion with minimal oversight. Comfort operating in ambiguous situations and making good judgment calls about what to build, what to delegate, and what to deprioritize.

Compensation & benefits

Salary

USD 240,000 – 320,000 (annual)

Stock options

Available

Benefits

Equity Participation

Grant of company stock options providing long-term upside participation in Sentry's growth as a trusted platform used by over 200,000 organizations globally.

Comprehensive Health Insurance

Group health insurance coverage including medical, dental, and vision plans designed for employees at a rapidly growing technology company.

Paid Time Off

Competitive paid time off policy allowing substantial vacation days and work-life balance, critical for sustaining high performance on challenging technical projects.

Incentive Compensation

Performance-based bonus structure tied to company and individual achievement, recognizing impact on Sentry's mission and engineering efficiency.

Professional Development

Access to training, conferences, and learning opportunities to stay current with rapidly evolving AI, infrastructure, and software engineering practices.

Remote Work Flexibility

Flexibility in work location and arrangement, enabling work that fits your lifestyle while collaborating effectively with a distributed team.

Collaborative Engineering Culture

Work environment emphasizing technical excellence, cross-team collaboration, and building tools that solve real developer pain points at scale.

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