Staff Software Engineer, Developer Productivity - Rails

About the Role:

As an engineer on the Developer Productivity Rails team, you'll work at the heart of Gusto's core applications, championing Ruby, Rails, and related technologies so that hundreds of product engineers can ship faster and more confidently. You'll modernize foundational systems, build reusable tools and patterns, and drive automation (including AI-assisted tooling) that scales our Rails applications as the number of services and engineers grows. This is high-leverage work: the improvements you make ripple nearly every engineering team at Gusto.

About the Team:

The Developer Productivity Rails team empowers Gusto engineers by keeping our core applications modern, up to date, and productive to work in. We own Rails and Ruby upgrades across all services, maintain shared libraries and CI infrastructure, and build the tooling and standards that make it easy to do the right thing, for humans and AI agents alike. We're a small team with an outsized ownership footprint, which means a high degree of autonomy and freedom to shape how engineering works at Gusto.

Here’s what you’ll do day-to-day:

• 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

Here’s what we're looking for:

• 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

Our cash compensation amount for this role is targeted at $190,000-$215,000 /yr in Denver & most remote locations, and $220,000-$250,000 /yr for San Francisco, Seattle & New York. Final offer amounts are determined by multi