Software Engineer (Python, TypeScript)

About The Company
At Gusto, we are dedicated to transforming the small business economy by providing comprehensive HR, payroll, benefits, and financial services. Our mission is to empower small business owners to focus on their craft and customers by handling the complex and time-consuming administrative tasks. With a presence in Denver, San Francisco, and New York, Gusto proudly supports over 400,000 small businesses nationwide. Our commitment to fostering an inclusive and innovative workplace is reflected in our Total Rewards philosophy, which emphasizes employee growth, well-being, and recognition. We believe that a diverse workforce enhances our ability to serve our diverse customer base and drives our continued success.
About The Role
We are seeking a highly skilled and experienced Software Engineer to join our Developer Productivity Rails team. In this role, you will work at the core of Gusto’s application infrastructure, championing Ruby, Rails, and related technologies to enable hundreds of product engineers to deliver features more efficiently and confidently. Your primary focus will be on modernizing foundational systems, developing reusable tools and patterns, and driving automation—including AI-assisted tooling—that scales with our growing engineering organization. This position offers the opportunity to make high-impact contributions that influence nearly every engineering team at Gusto, ensuring our systems remain robust, scalable, and maintainable.
Qualifications

• 10+ years of professional software development experience with strong architecture and systems thinking skills
• Deep expertise in Ruby on Rails or equivalent backend technologies (Python, Go, TypeScript) with a willingness to deepen Rails knowledge
• Experience building developer tooling, shared libraries, or platform infrastructure that supports large engineering teams
• Excellent communication skills with the ability to collaborate effectively and understand the needs of internal customers
• Familiarity with AI-assisted development workflows (e.g., Cursor, Copilot) and enthusiasm for applying AI to infrastructure and automation
• Experience with type systems (Sorbet, RBS), CI/CD pipelines, code generation, static analysis, or large-scale framework upgrades
• Strong inclination towards observability, automation, and building repeatable processes

Responsibilities

• Identify and resolve inefficiencies in tooling, frameworks, and feedback mechanisms to enhance developer productivity
• Lead Rails and Ruby upgrades across Gusto’s core applications, developing automation and AI-assisted tooling to facilitate this work at scale
• Create and maintain reusable libraries, gems, and patterns to promote best practices and accelerate team onboarding
• Manage and improve shared CI/CD tooling, including static analysis, guardrails, and migration checks
• Partner with product engineering teams to understand their pain points and deliver iterative solutions that improve their workflows
• Develop observable standards and scorecards to monitor the health and maturity of services, making insights actionable
• Leverage AI tools and automation agents to enhance development workflows and contribute to the organization’s AI strategy

Benefits

• Competitive salary aligned with experience and location, ranging from $190,000 to $250,000 annually
• Comprehensive health insurance coverage including medical, dental, and vision plans
• Generous paid time off and holiday policies to support work-life balance
• 401(k) retirement savings plan with company contributions
• Flexible work arrangements, including remote work options and hybrid models in designated offices
• Professional development opportunities and continuous learning support
• Inclusive and diverse workplace culture that values innovation and collaboration

Equal Opportunity
Gusto is proud to be an equal opportunity employer. We do not discriminate based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or any other legally protected characteristic. We are committed to fostering an inclusive environment and providing reasonable accommodations for qualified individuals with disabilities and disabled veterans throughout the application and employment process. We encourage applicants from all backgrounds to apply and look forward to welcoming diverse talents to our team.