Staff Software Engineer, AI Developer Tooling

Sentry2 days ago

Location

San Francisco, California

Type

Full Time

Salary

USD 240,000 – 320,000

Level

Staff

Role

Staff Software Engineer

Posted

Apr 8, 2026

Full TimeStaff

The role

Summary

Sentry is seeking a Staff Software Engineer specializing in AI Developer Tooling to revolutionize software development workflows. The role focuses on building AI-ready systems, creating advanced coding agent infrastructure, and improving engineering productivity across the organization through innovative tooling and automation strategies.

What you'll do

AI Systems Integration: Audit and transform Sentry's internal developer systems to be API-ready for AI coding agents, enabling end-to-end operational capabilities.

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

Engineering Automation: Automate high-volume, low-priority engineering tasks such as security dependency upgrades, minor bug fixes, and routine maintenance.

Productivity Enhancement: Design and implement internal tools like productivity dashboards, AI-assisted issue triage, and CI/CD optimizations to reduce engineering toil.

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

What we look for

Technical

System DesignStrong software and system design fundamentals with experience in large-scale distributed systems

AI ToolingHands-on experience with AI coding tools and agents, understanding of AI-assisted development workflows

Developer InfrastructureExperience building tools or workflows that improve developer productivity, including CI/CD and developer infrastructure

Education

Computer ScienceBachelor's or equivalent practical experience in software engineering, computer science, or related technical field

Experience

Senior Engineering Experience10+ years of comprehensive software engineering experience with proven track record of driving cross-team technical initiatives

Skills

Required skills

AI Coding ToolsDeep understanding and practical experience with AI coding agents and development workflows

Systems ThinkingAbility to pattern-match across infrastructure, backend, and developer tooling domains

Cross-Team CommunicationStrong ability to communicate complex technical concepts and influence without direct authority

Nice to have

Machine Learning ContextPrior experience or exposure to machine learning concepts (not strictly required)

Developer ExperienceBackground in engineering productivity programs or developer experience optimization

Code Review ToolingFamiliarity with code review tools, static analysis, or automated PR pipelines

Compensation & benefits

Salary

USD 240,000 – 320,000 (annual)

Benefits

Competitive Compensation

Base salary range of $240,000 to $300,000 with potential additional compensation

Hybrid Work Model

Flexible work arrangement with in-office collaboration days (Mondays, Tuesdays, Thursdays)

Employee Stock Options

Potential equity grants as part of compensation package

Health Insurance

Comprehensive group health insurance coverage

Inclusive Culture

Commitment to diversity, equity, and inclusion in the workplace

Interview process

1
Initial Screening — Preliminary review of resume and qualifications
2
Technical Discussion — In-depth conversation about AI coding tools, developer infrastructure, and system design experience
3
Technical Assessment — Practical evaluation of system design and AI tooling skills
4
Leadership Interview — Discussion with senior technical leadership to assess cross-team influence and strategic thinking
5
Final Interview — Comprehensive review and potential offer discussion