Senior Staff Software Engineer, Benefits

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves.

About the Role

As a Staff Software Engineer on the Benefits Advisory team, you will be directly accountable for key architectural improvements to Gusto's benefits platform. This is a full-stack role where you will design and build platform capabilities that enable customers to explore, apply for, and maintain their benefits within your product area.

Your work will focus on transforming our benefits opportunity, shopping, and renewal flows, creating clear system boundaries that enable efficient reuse and increased scalability, allowing the ability to offer a wider variety of products more quickly. You will design services that continue to scale the organization, with an emphasis on enabling novel AI-driven interfaces to deliver a delightful benefits shopping experience.

Key Responsibilities

• Architect and evolve customer-facing web platforms with a focus on scale and performance.
• Build innovative AI interfaces to best assist customers.
• Design, build, and maintain shared services to enable rapid iteration on product offerings.
• Implement and optimize key workflows for a best-in-class customer experience.
• Write high-quality, well-tested code across the stack, leveraging AI-powered tools to accelerate development and improve reliability.
• Support, mentor, and up-level fellow engineers on the team, helping establish best practices for AI-native design patterns.
• Partner cross-functionally with Marketing, Sales, Operations, and leadership to translate business needs into technical solutions.
• Influence the technical roadmap for your area of the Benefits Advisory platform, ensuring alignment with Gusto's AI-native strategy and team goals.

Qualifications

Required

• 8+ years of experience building scalable full-stack web applications with expertise in both frontend (React, TypeScript) and backend (API development, data modeling, database schema design).
• Extensive experience building AI interfaces, iterating on prompts, and maintaining high-quality evals.
• Extensive experience applying AI tools to accelerate full-stack development, improve code quality, and build intelligent user experiences.
• Familiarity with AI-driven personalization patterns and willingness to experiment with AI techniques to improve the benefits shopping experience.
• Deep experience in CI/CD and observability best practices.
• Ability to act as a thought partner for both technical and business teams.
• A balance of pragmatic execution and long-term architectural thinking.
• Experience enabling productivity across large engineering organizations.

Preferred

• Direct familiarity with React and Ruby on Rails.
• Experience with robust recommendation systems.
• AI architecture and scalability for reliable platform services.