Principal Software Engineer, Money Group

Gusto•San Francisco, NY

28d•$214,000 - $300,000•Hybrid

About The Position

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. 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.

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,

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.