Principal Software Engineer - Contractors Payroll

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: As the Principal Engineer for the Contractors team, you will play a pivotal role in shaping the future of Gusto’s flagship Payroll product—one of the core pillars of our platform. You will design, build, and scale the capabilities that power essential experiences for our customers. Working collaboratively with product managers, designers, and other engineers, you will deliver impactful features that meet customer needs and elevate user experiences. As a Gusto Engineer at this level, you’ll guide projects end-to-end—shaping initial feature specifications, driving architectural decisions to bring systems closer to their desired end states, executing on complex initiatives, and maintaining code that powers mission-critical functionality. Beyond technical contributions, you’ll help define and contribute to the broader strategy of how Gusto continues to build and scale its Payroll product. If you’re excited about solving complex, high-impact problems and want to contribute to a product that touches the lives of millions, we’d love to have you on board! About the Team: Payroll serves as Gusto's core product, used by each of our 500,000+ customers and contributing significantly to our annual recurring revenue of over $800,000,000. Although we hold the leading market position for SMBs in the US, the market remains highly fragmented, with an estimated 90% still in need of a superior solution. The Contractors team empowers businesses to onboard and pay contractors in 120+ countries with ease and speed. This includes critical functionalities such as payroll setup, preparation, and submission, historical reporting, time tracking, and shift scheduling. As a key member of this team, you’ll have the opportunity to make a profound impact on both the product and the customers who depend on it daily. Here’s what you’ll do day-to-day: Architect, build, and maintain scalable, secure, and resilient backend systems to support Gusto’s Payroll products. Function as a Technical Lead across multiple teams in Pay Group, helping us keep engineers unblocked and deliver high-quality work supporting our long-term goals. Help scale one of the largest Ruby/Rails and TypeScript/React applications in the world. Collaborate on complex and ambiguous problems with partnerships from Engineering, Product Management, Design, Data Science, Compliance, Operations, and other cross-functional teams. Mentor and grow fellow engineers working to create holistic and scalable solutions. Drive the product development process from concept to launch, delivering delightful products that make payroll, taxes, and compliance simple and easy. Engage in a highly supportive environment working with others to drive productivity and innovation. Here’s what we're looking for: 15+ years of professional software development experience. Experience as a tech lead, overseeing and successfully delivering projects that span multiple teams. Enthusiasm for a collaborative, test-driven development environment. Proven experience building and maintaining resilient backend systems that support customer-facing products, including optimizing existing systems for performance, reliability, and scalability. Ability to produce maintainable, structured, and well-documented code. Expertise in developing and maintaining RESTful APIs, GraphQL endpoints, and backend services, ensuring seamless integration with frontend systems and third-party services. Demonstrated ability in scaling engineering organizations, with a strong focus on individual and team development and mentorship. Experience in highly cross-functional environments working on highly complex products. Ability to clearly communicate technical complexity and facilitate informed trade-offs among stakeholders. Experience using AI tools to build, test, and iterate on products quickly. Understanding of how to evaluate AI-driven outputs using clear success criteria. A commitment to staying current on emerging backend technologies and AI frameworks and patterns, regularly experimenting with new approaches. Willingness to contribute to shared tools or templates that enhance the speed and safety of AI experimentation. Our cash compensation amount for this role is targeted at $251,000-$309,000 /yr for New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above. 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. 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