Principal Software Engineer, Money Group

Gusto is on a mission to grow the small business economy by providing essential services like payroll and HR. They are seeking a Principal Engineer to lead technical initiatives across multiple teams in the Money Group, focusing on building a unified financial platform for small businesses.

Responsibilities:

• Serve as a Technical Lead across multiple teams in the Money Group – setting architectural direction, unblocking engineers, and ensuring high-quality delivery aligned with long-term goals
• Define the north-star architectural vision for the Money Group and continuously identify shorter-term projects that move us toward it
• Architect the convergence of Gusto's People Stack (payroll, HR, benefits) and Finance Stack (banking, accounting, payments, lending) into a unified platform for small businesses
• Lead service migration from a large Ruby-on-Rails monolith into a service-oriented architecture, defining clean domain boundaries across money movement, lending, and tax
• Lead technical due diligence – evaluating codebases, data models, and engineering teams for compatibility with Gusto's platform
• Manage a complex partner ecosystem
• Build prototypes and proofs-of-concept to de-risk new ideas and unblock product decisions quickly
• Tackle complex, ambiguous problems in close partnership with Product Management, Design, Data Science, Compliance, and Operations
• Drive AI-native architecture decisions – from LLM-powered transaction categorization and tax optimization to conversational financial management experiences
• Act as a technical consultant across all Money sub-teams – Consumer, Business, Tax Credits, Payments – ensuring architectural coherence across the group
• Set the bar for technical excellence – through code, design reviews, and the standards you hold the group to
• Mentor fellow engineers, contribute to the growth of senior and staff engineers, and help build healthy, high-performing teams

Requirements:

• 15+ years of software engineering experience (successful applicants typically meet or exceed this)
• Deep expertise in distributed systems, particularly in payments or fintech – including data modeling for financial systems, consistency guarantees for money movement, and compliance-aware architecture
• Proven track record of engineering, scaling, and operating large, interconnected production systems
• Experience setting long-term technical vision and driving multi-year architectural transformations – not just executing migrations, but identifying the right boundaries, sequencing the work across teams, and ensuring strong technical stewards drive execution
• Experience working across multiple teams, influencing both technical direction and product strategy. Demonstrated ability to own group-level OKRs and be accountable for the technical strategy that delivers them
• Experience navigating decisions for core infrastructure, particularly in fintech – evaluating APIs, negotiating technical contracts, and leading integration from evaluation through production
• Ability to bring clarity to complex problems – communicating technical tradeoffs to non-technical stakeholders, identifying significant risks or opportunities before others, and driving decisions
• A track record of raising the technical bar – through code quality, design rigor, testing and security best practices, and the standards you set for those around you
• A track record of filling whatever role the group needs – from hands-on prototyping to strategic planning to firefighting – with a bias toward action
• Experience in complex, highly regulated domains (e.g., fintech, payments, banking, lending)