Principal Engineer

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k) s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve.

Learn more about our Total Rewards philosophy.

About the Role

We’re hiring a seasoned engineer to join our Integrated Benefits team that works on improving our existing systems for extensibility and scalability, and building the future of Gusto's Benefits ecosystem. As a Gusto Software Engineer at this level, you’ll be guiding projects end-to-end by influencing initial feature specs, understanding how to take existing systems closer to desired end states, executing on projects, and maintaining code that powers core experiences.

The Integrated Benefits team focuses on the integration of users' existing benefits providers and the development of Voluntary Life and Disability (vLiDi) products. In this role, you will operate as a Builder, focusing on the architecture of complex and interconnected technical systems. You will have a scaled impact across the wider Benefits engineering organization by augmenting our Product Engineering culture with reusable capabilities and solid technical foundations.

We are looking for engineers who are ready to solve deep, ambiguous architectural puzzles and apply AI tools to accelerate development and deliver new product capabilities. If you’re interested in building elegant software with far-reaching effects in our modern economy, join us!

About the Team

The Integrated Benefits (IB) team operates with a heart for complex challenge within the larger Gusto Benefits organization, serving as the critical link for users' existing benefits providers and the development of Voluntary Life and Disability (vLiDi) products. Our work enables customers to work with an external broker while still leveraging Gusto’s people platform to seamlessly integrate and manage their benefits.

We offer the unique opportunity to solve deep, ambiguous architectural puzzles and integrate our systems with the org-wide push for AI. This high-performing, independent group values humor and casual connection, fostering an environment that enjoys pairing and problem-solving together.

Here’s what you’ll do day-to-day

• Function as a Technical Lead within the Integrated Benefits team, using leadership and soft power to influence the wider Benefits engineering organization of ~60 engineers.

• Design, build, and test the solid technical foundations and reusable "LEGO blocks" that support our Voluntary Life and Disability (vLiDi) products and broker integrations.

• Help scale our platform by architecting complex, interconnected technical systems and executing within a Ruby on Rails environment.

• Collaborate on complex and ambiguous problems, partnering with cross-functional teams to solve deep architectural puzzles and take existing systems closer to desired end states.

• Mentor and grow fellow engineers, fostering a culture of ownership and mentorship within a high-performing, self-organized team.

• Drive the product development process for platform capabilities, from influencing initial feature specs to maintaining code that powers core experiences.

• Improve the productivity of our product engineering culture by building tools and shared capabilities that allow teams to move faster.

• Continuously apply AI tools to accelerate development, using AI to build, test, and iterate quickly while staying curious about emerging frameworks and patterns.

Here’s what we're looking for

• 12+ years of relevant professional experience in software engineering.

• Able to build maintainable, structured, well-documented code, with specific proficiency in Ruby on Rails and a strong focus on architectural patterns.

• Strong knowledge of data structures, data modeling, and system design, particularly within complex, interconnected systems.

• Experience working across multiple teams, influencing both product and team direction by…