Principal Software Engineer - Pay Group Engineering

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 and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. 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. AI experience requirements vary by role and will be assessed during the interview process. About the Role We're hiring a seasoned engineer to help stand up a newly formed team dedicated to State Tax Registration & Closure — the systems that get Gusto customers registered with state tax agencies when they start operating in a new state, and cleanly closed out when they stop. As a Principal Software Engineer, you'll shape this team's technical direction from the ground up: defining the architecture, evolving legacy registration and closure workflows toward a more scalable and automated future, and partnering closely with Compliance and Operations to keep customers in good standing across every state they touch. This role starts focused: get State Tax Registration & Closure onto solid technical footing in the first year. From there, we expect your scope to grow — taking on broader technical influence across Company Group as you prove out the team's foundation. If you're excited about building elegant software with far-reaching effects in the modern economy, and about growing your impact alongside a newly forming team, we'd love for you to join us! About the Team Company Group builds the products that help small businesses become — and stay — legitimate, compliant companies, tackling the "back office" work that has everything to do with keeping a business in good standing. That spans forming a legal entity, registering and filing with state and local agencies, business insurance, and the ongoing compliance obligations that come with operating across multiple states. Our Products Business Compliance & Entity Management: Owns the products that help customers form and maintain their legal entity — filings, registered agent services, annual reports, and the ongoing paperwork that keeps a business in good legal standing. Start Your Business: Helps first‑time founders go from idea to registered, compliant business — entity formation, EIN setup, and the guidance new business owners need to get started with confidence. Solo: Builds a back-office experience tailored to solo entrepreneurs and S‑corp owners, simplifying the compliance and tax decisions that typically require an accountant. Business Insurance: Owns the end‑to‑end business insurance experience, helping customers find and maintain the coverage (workers' comp, general liability, PEO) their state and industry require. State Tax Registration & Closure (what you'll build): The future of how Gusto customers register for state payroll taxes as they expand into new states, and how those state tax accounts get cleanly closed out when a customer stops operating there. Multi‑state registration and closure today is a maze of shifting agency requirements, inconsistent (and often paper‑based) processes, and manual workarounds — the job here is to build AI‑first, agentic automation that takes action on a customer's behalf (filling out and filing registration paperwork, following up with agencies, closing accounts) instead of routing everything through manual review, giving customers and Gusto's Compliance and Operations teams confidence at scale. Here's what you'll do day-to-day: Function as the founding Technical Lead for State Tax Registration & Closure, standing up the team's technical foundation and setting technical direction from day one. Design, build, and test the systems that register and close out Gusto customers' state tax accounts as they start and stop operating across all 50 states. Grow your remit over your first year — from building and scaling State Tax Registration & Closure to taking on broader technical influence across Company Group. Help scale one of the largest Ruby on Rails and TypeScript/React applications in the world. Collaborate on complex and ambiguous problems in partnership with Engineering, Product Management, Design, Data Science, Compliance, Operations, and other cross‑functional teams. Mentor and support fellow engineers in creating holistic, scalable solutions. Drive the product development process from concept to launch, delivering products that make company compliance simple and easy. Build services, tools, and APIs that make Gusto's engineering, compliance, and operations teams more effective. Work in a highly supportive environment that fosters collaboration, productivity, and innovation. Stay current with advancements in AI and Machine Learning, applying this knowledge to our projects. Here's what we're looking for: 15+ years of experience (successful applicants typically meet or exceed this). Ability to build maintainable, structured, and well‑documented code. Strong knowledge of data structures, data modeling, and system design. Experience working across 3+ teams, influencing both product and team direction. Experience developing platform products that are relied on company‑wide. Proven background in engineering, designing, building, and supporting large‑scale production systems. Ability to bring clarity and simplicity to complex problems, communicate technical complexity, and facilitate informed trade‑offs with major stakeholders. Experience operationalizing and scaling large, interconnected production systems. Enthusiasm for a collaborative, test‑driven environment. Experience in complex, highly regulated domains (e.g., HR, Payroll, Taxes, Compliance), ideally including direct integration with government agencies and their idiosyncratic systems. Experience using AI tools to build, test, and iterate on products quickly. Understanding of how to evaluate AI‑driven outputs using clear success criteria. Experience building agentic systems that take action and/or automate toil, and a commitment to staying current on emerging backend technologies and AI frameworks and patterns. Willingness to contribute to shared tools or templates that enhance the speed and safety of AI experimentation. Our cash compensation for this role is targeted at $239,000–$264,000 per year in Denver and most remote locations, and $280,000–$309,000 per year in San Francisco, Seattle, and New York. Stock equity is offered in addition. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the ranges 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. 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. 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