Principal Software Engineer

About Gusto

Gusto is a leading provider of cloud-based payroll, benefits, and HR management solutions dedicated to empowering small businesses across the United States. With a mission to grow the small business economy, Gusto simplifies complex processes such as payroll, health insurance, 401(k) administration, and compliance management, allowing business owners to focus on their core activities and customer relationships. The company boasts a diverse team operating from Denver, San Francisco, and New York, supporting over 400,000 small businesses nationwide. Gusto’s commitment to innovation, inclusivity, and customer-centricity has established it as a trusted partner for entrepreneurs seeking reliable and scalable HR solutions.

About The Role: Principal Software Engineer

Gusto is seeking an experienced Principal Software Engineer to join the Pay Group Engineering team, focusing on core platform capabilities that enhance the scalability, extensibility, and reliability of Gusto’s Payroll and Tax systems. In this strategic role, you will lead end-to-end projects, influence system architecture, and guide cross-functional teams to deliver high-quality, compliant payroll solutions for millions of users. Your expertise will help shape the future of Gusto’s payroll infrastructure, ensuring it remains robust, flexible, and aligned with industry standards and regulatory requirements. This position offers an opportunity to work on large-scale, complex systems, leveraging your technical leadership skills to drive innovation in a highly regulated and dynamic domain.

Qualifications

• At least 15+ years of professional software engineering experience.
• Proficiency in building maintainable, structured, and well-documented codebases.
• Strong knowledge of data structures, data modeling, and system design principles.
• Experience collaborating across three or more teams, influencing product and technical direction.
• Hands-on experience developing platform products relied upon throughout an organization.
• Proven track record of engineering, designing, building, and supporting large-scale production systems.
• Ability to simplify complex problems and communicate technical concepts effectively to stakeholders.
• Experience operationalizing and scaling interconnected, highly regulated systems such as HR, payroll, or tax platforms.
• Familiarity with AI tools for rapid product development, testing, and iteration.
• Understanding of evaluating AI outputs using clear success criteria and integrating AI-driven features responsibly.
• Commitment to staying current with emerging backend technologies, AI frameworks, and industry best practices.
• Willingness to contribute to shared tools, templates, and processes that accelerate AI experimentation and deployment.

Responsibilities

• Serve as a technical leader across multiple teams within Payroll Services, providing guidance and removing blockers to ensure timely, high-quality delivery.
• Design, develop, and test foundational components that support compliant payroll processing for millions of users.
• Contribute to scaling and maintaining one of the largest Ruby/Rails and TypeScript/React applications globally.
• Collaborate with cross-functional partners, including Engineering, Product Management, Design, Data Science, Compliance, and Operations, to solve complex and ambiguous problems.
• Mentor and grow engineering teams, fostering a culture of technical excellence and continuous learning.
• Drive product development from concept through launch, ensuring solutions are scalable, reliable, and user-centric.
• Enhance team productivity and morale by building effective tools, APIs, and services that streamline workflows.
• Stay abreast of advancements in AI and machine learning, applying innovative solutions to improve product features and processes.
• Evaluate and incorporate AI-driven outputs, establishing clear success metrics and ensuring ethical and compliant implementation.

Benefits

• Competitive cash compensation, targeted at $215,000 to $252,000 annually in Denver and most remote locations, and $251,000 to $295,000 in San Francisco, Seattle, and New York.
• Stock equity options to align long-term incentives with company success.
• Flexible work arrangements with designated in-office days, fostering collaboration and team cohesion.
• Comprehensive health insurance plans, including medical, dental, and vision coverage.
• Generous paid time off and holidays to support work-life balance.
• Professional development opportunities, including training, conferences, and continuous learning programs.
• A diverse and inclusive workplace that values innovation, collaboration, and integrity.

Key skills/competency

• Software Engineering
• System Architecture
• Payroll Systems
• Tax Compliance
• Ruby on Rails
• TypeScript React
• Large-scale Systems
• Technical Leadership
• AI Machine Learning
• Data Modeling
• Scalability