Senior Staff Software Engineer, Integrated Benefits Platform

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 Team The Integrated Benefits (IB) team sits within Gusto’s broader Benefits organization and owns some of the most technically complex areas of the platform. The team enables customers to work with external brokers while seamlessly managing benefits through Gusto, including the development and evolution of Voluntary Life and Disability (vLiDi) products. Our work spans deeply interconnected systems, external integrations, and regulated domains. As Gusto continues its transition toward AI-native systems, the Integrated Benefits team plays a critical role in modernizing platform foundations and enabling intelligent, scalable product experiences. About the Role As a Senior Staff Software Engineer on the Integrated Benefits team, you will own and evolve key architectural areas within the Integrated Benefits platform. You will drive architectural improvements that increase system scalability, extensibility, and resilience while shaping the future of Gusto’s Benefits ecosystem. This role operates with high autonomy and scope. You will make and influence architectural decisions within your domain, partner across teams to align on technical direction, and guide systems through complex transitions. Success in this role requires comfort navigating ambiguity, leading through influence rather than authority, and balancing immediate delivery with long-term platform health. Your work will have durable impact across the Benefits organization and will shape how teams build, integrate, and evolve benefits products at Gusto. What You’ll Do Own and evolve the architecture for key areas of the Integrated Benefits platform, ensuring systems are scalable, reliable, and adaptable to future needs. Drive architectural decisions and technical strategy within your domain, making informed tradeoffs that balance business goals, technical constraints, and long-term sustainability. Contribute to the technical roadmap for your area of the platform, aligning your work with team objectives and broader Benefits engineering priorities. Design and build shared platform capabilities that support Voluntary Life and Disability (vLiDi) products and broker integrations across the Benefits ecosystem. Lead the technical approach to complex, ambiguous problem spaces, partnering with product, design, and cross-functional stakeholders to define end states and guide systems toward them. Identify cross-team dependencies and influence alignment on architectural patterns, standards, and best practices. Raise the technical bar by mentoring engineers through design reviews and, architectural guidance. Apply AI tools to accelerate development, improve code quality, and enable intelligent product capabilities, while evaluating emerging frameworks using clear success criteria. Contribute to shared tooling, patterns, or standards that enable safe and effective experimentation, including AI-driven workflows, across teams. What We’re Looking For Successful applicants will typically have 10+ years of software engineering experience building and supporting production software systems. Significant experience designing and evolving complex backend systems, including deep experience in Ruby on Rails–based environments. Demonstrated ability to own architectural decisions within a product domain and influence technical direction across teams. Experience building or contributing to platform capabilities or shared systems depended on by multiple teams. Strong foundation in system design, data modeling, and working with complex, interconnected production systems. Comfort operating in ambiguous problem spaces and leading technical decision-making through uncertainty. Strong communication and collaboration skills, with the ability to influence engineers and cross-functional partners without formal authority. Experience applying AI tools in production engineering workflows to improve development velocity, system quality, or product behavior. Familiarity with evaluating AI-driven outputs using well-defined success criteria and operational constraints. Nice to Haves Experience working in highly regulated domains such as Benefits, Payroll, HR, Taxes, or Compliance. Experience designing or evolving large-scale integration platforms or service-oriented architectures. Prior work supporting external partners or third-party integrations. Experience contributing to internal developer platforms, shared tooling, or technical standards. Exposure to AI-driven systems beyond experimentation, including monitoring, evaluation, or governance. Compensation Our cash compensation amount for this role is targeted at $223,000/yr to $265,000/yr for both San Francisco & New York locations. Stock equity is additional. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above. Location Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately two days per week (or more depending on role). Note: The San Francisco office expectations encompass both the SF and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision 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 other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.