Staff Software Engineer, AI Developer Tooling

Sentry2 weeks ago

Location

San Francisco, California

Type

Full Time

Salary

USD 240,000 – 320,000

Level

Staff

Role

Staff Software Engineer

Posted

Jun 4, 2026

Full TimeStaff

The role

Summary

Sentry is seeking a Staff Software Engineer specializing in AI Developer Tooling to revolutionize how AI coding agents integrate into the software development lifecycle. The ideal candidate will build innovative tooling that enables AI agents to seamlessly interact with internal systems, automate engineering processes, and enhance developer productivity across the organization.

What you'll do

AI Systems Integration: Audit Sentry's internal developer systems and make them API-ready for AI agents, prioritizing and driving programmatic exposures for end-to-end agent operations.

AI Tooling Development: Build harness tooling, context systems, and feedback loops to generate high-quality, repository-aware pull requests with automated pre-review checks and quality measurement.

Engineering Automation: Automate high-volume, low-priority engineering work including security dependency upgrades, minor bug fixes, and routine maintenance to optimize engineering focus.

Internal Tool Development: Design and construct internal tools to enhance engineering effectiveness, including productivity dashboards, AI-assisted issue triage, and CI/CD optimizations.

Organizational Optimization: Identify and remove engineering friction by using data and direct observation to recommend solutions and build cross-team consensus for strategic improvements.

What we look for

Technical

AI Coding ToolsDeep understanding and hands-on experience with AI coding agents and development workflows

System DesignStrong software and system design fundamentals with ability to work across infrastructure, backend, and developer tooling domains

API DevelopmentExperience in creating programmatic interfaces and exposing internal systems for automated interactions

Education

Technical BackgroundAdvanced degree in Computer Science, Software Engineering, or equivalent professional experience preferred

Experience

Engineering Tenure10+ years of comprehensive software engineering experience

Cross-Team InitiativesProven track record of driving technical initiatives across multiple teams to successful completion

Skills

Required skills

AI DevelopmentPractical experience with AI coding tools and agents

Cross-Functional CommunicationAbility to clearly communicate technical concepts and influence without direct authority

Systems ThinkingCapacity to understand and optimize complex engineering ecosystems

Nice to have

Large-Scale SystemsExperience with distributed systems or monolith decomposition

Developer ExperienceBackground in engineering productivity programs or tooling

Code Review ToolsFamiliarity with static analysis and automated PR pipeline technologies

Compensation & benefits

Salary

USD 240,000 – 320,000 (annual)

Benefits

Competitive Compensation

Salary range of $240,000 to $300,000 with potential equity grants

Health Insurance

Comprehensive group health insurance coverage

Flexible Work

Hybrid work arrangement with location flexibility

Professional Growth

Opportunity to work at the forefront of AI-assisted software development

Interview process

1
Initial Screening — Phone or video interview to assess background and initial fit
2
Technical Assessment — Comprehensive evaluation of technical skills, system design capabilities, and AI tooling experience
3
Leadership Interview — Discussion with senior technical leadership to assess cross-team collaboration and strategic thinking
4
Final Panel Interview — Comprehensive interview with potential team members and engineering leadership