Principal Software Engineer, Money Group

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: We're hiring a Principal Engineer to serve as a Technical Lead across multiple teams in the Money Group – Gusto's fastest-growing organization and a cornerstone of the company's transformation into the Small Business Finance Platform. You'll define the long-term technical vision for systems that power cash flow management, lending, expense controls, invoicing, payments, and tax optimization (something about consumer financial health?)– ensuring the architecture scales as we grow. This role spans strategy and execution: setting architectural direction across 5+ teams, vetting external partners, prototyping new product lines to unblock product decisions, extracting services from our monolith, and mentoring the engineers around you. You'll be the person who fills whatever role the group needs to hit its goals – from hands-on coding to strategic planning to unblocking other teams. If you're excited about building financial infrastructure with real impact on the people and businesses that power the modern economy, we'd love for you to join us. About the Team: Money is Gusto's fastest-growing group, building financial products for both sides of the employment relationship. For small businesses, we're extending the category of employer-facing financial services – bill pay, invoicing, working capital, expense cards, and cash flow insights that help SMBs get paid faster and pay others with confidence. For employees, we build tools that reduce financial stress: on-demand pay, high-yield cash accounts, automated savings, and credit-building features. This is a deeply technical domain spanning payments infrastructure, lending, multi-party integrations, and mobile-first experiences – with the complexity and scale to match. Together, these teams are building toward a unified financial operating system for small businesses – accounting, banking, payments, lending, and tax – all connected to Gusto's payroll and people platform. Our unique advantage is Gusto's authority over payroll data, which we leverage to build a payroll-confidence engine no standalone fintech can replicate. Here’s what you’ll do day-to-day: 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 acr ... (truncated, view full listing at source)