Hybrid Staff Software Engineer, Developer Productivity – Rails

at Gusto

• Job title: Staff Software Engineer, Developer Productivity – Rails
• Job type: Full Time
• Experience level: Lead
• Salary: $190,000 - $215,000 per year
• Degree requirement: No Education Requirement
• Tech skills: Python, Ruby, Ruby on Rails, TypeScript, Go
• Location requirements: Hybrid, Toronto, United States

About the role

• Staff Software Engineer on Developer Productivity team at Gusto, enhancing Rails applications and tools for engineers. Collaborate with teams and improve productivity with automation and AI-assisted tooling.

Responsibilities

• Seek out and solve inefficiencies in the tooling, frameworks, and feedback mechanisms available to product engineers to improve developer productivity
• Advance Rails and Ruby upgrades across Gusto's core applications, developing automation and AI-assisted tooling to scale this work across a growing number of services
• Build and maintain reusable libraries, gems, and patterns that commonize best practices so teams are productive from day one in any service
• Steward and improve shared CI tooling, including Danger, Sorbet, RuboCop, database migration checks, and other developer-facing guardrails
• Collaborate with product engineering teams as their partner and 'internal customer advocate,' understanding their pain points and shipping solutions iteratively
• Contribute to observable standards and scorecards that make the health and maturity of our services visible and actionable
• Leverage AI tools (Cursor, Claude, automation agents) as part of your daily workflow and help shape how AI augments developer productivity across the organization

Requirements

• 10+ years of professional software development experience with solid architecture and systems thinking skills
• Deep working knowledge of Ruby on Rails, or equivalent backend experience (Python, Go, TypeScript) with a genuine willingness to go deep on Rails
• Experience building developer tooling, shared libraries, or platform infrastructure that serves 10s or 100s of engineers
• Comfort working with colleagues as your 'customers,' you're a great communicator who can plan, document, consult, and collaborate effectively on changes that affect how others work
• Familiarity with AI-assisted development workflows (e.g., Cursor, Copilot, or similar) and enthusiasm for applying AI to scale infrastructure and automation work
• Experience with some combination of: type systems (Sorbet/RBS), CI/CD pipelines, code generation, linting/static analysis, or framework upgrades at scale
• A tendency toward making things observable, repeatable, and automated, you'd rather build the machine than do it by hand twice.

Benefits

• Health insurance
• 401(k) plans
• Paid time off
• Flexible work arrangements