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:
At Gusto, we're on a mission to create a world where work empowers a better life. For the hundreds of thousands of small businesses we serve, this mission begins with one of their most critical and high-stakes responsibilities: their financial wellness and ability to pay their team. The Head of Engineering, Money sits at the very heart of this promise.
We are seeking a strategic and execution-focused leader to lead our end-to-end Money platform and product engineering organization. This leader will own the technical vision, architecture, and delivery across Consumer Money, Business Money (including Tax Credits), Accounting, Expenses & Invoicing, and Payments.
This is a critical leadership role responsible for building secure, scalable, and compliant financial systems that power how customers move, manage, and understand their money. You will lead multiple engineering teams, partner closely with Product, Design, Risk, Compliance, and Finance, and drive operational excellence across high-scale, high-trust financial infrastructure. This is a rare opportunity to shape the future of a product that millions of people depend on for their financial stability. You'll be challenged to modernize essential platforms, drive the next wave of product innovation (from financial wellness to AI-powered automation), and build for massive scale and unflinching reliability. We're looking for a visionary leader who can inspire a large organization, navigate immense technical complexity, and ultimately help us make the work of paying a team disappear.
About the Team:
You'll be leading the Money Engineering team, a core part of Gusto's Fintech Products and the team most directly connected to our customers' peace of mind. We believe that financial wellness isn't just a feature - it’s the foundation of trust with every business we serve. We don't just build software; we take on the immense complexity of financial wellness so our customers can focus on their passions.
What You’ll Do:
- Defines and executes the long-term technical strategy for the Money platform, ensuring scalable, resilient, and compliant financial systems across consumer and business products.
- Drives platform thinking across payments, ledgers, accounting systems, and financial data infrastructure while meeting regulatory, security, and audit requirements.
- Leads and develops senior engineering leaders, fostering a high-performing, inclusive culture focused on accountability and customer impact
- Owns org design, capacity planning, and hiring strategy, while establishing clear ownership across product and platform teams
- Oversees delivery of high-quality financial products and complex cross-functional initiatives (e.g., money movement, tax credits, invoicing, expense management)
- Improves engineering velocity, operational excellence, and incident response, partnering with Risk, Compliance, and Legal for secure delivery
- Guides architecture for critical financial systems, including ledgers, payment orchestration, reconciliation, and reporting pipelines
- Champions best practices in distributed systems, data integrity, and fault tolerance, while driving observability, auditability, and technical modernization
Here’s what you’ll do day-to-day:
- Set the technical north star for Gusto's core payments and fintech platforms, guiding the evolution of our architecture toward greater scalability, reliability, and flexibility for the future.
- Build and nurture a world-class engineering organization of over 50, fostering a culture of excellence and investing deeply in the growth of our People Empowerers and senior technical leaders.
- Deliver with excellence on a high-stakes roadmap, leading your teams to execute complex, deeply technical projects that are fundamental to our customers' trust and our business's success.
- Drive the next generation of financial products innovation by partnering with product and design leaders to transform our customer experience from simply being possible to being truly magical.
- Uplevel our engineering craft and operational rigor, championing a culture of quality, continuous improvement, and ownership for the systems that form the bedrock of Gusto.
- Act as a key voice in Gusto's engineering leadership, collaborating across the company to influence strategy and ensure our payroll platform enables the ambitious future of our entire product ecosystem.
Here’s what we're looking for:
- 12+ years of engineering experience, including 5+ years leading senior engineering leaders.
- Proven experience building and scaling fintech, payments, accounting, or financial infrastructure systems.
- Experience owning regulated financial systems with strong compliance and audit requirements.
- Demonstrated success leading multi-team organizations (50+ engineers preferred).
- Deep understanding of payment systems, ledgers, reconciliation, and financial data integrity.
- Experience with distributed systems at scale.
- Familiarity with regulatory frameworks impacting financial products.
- Strong data and platform architecture instincts.
- Strategic thinker with strong execution discipline.
- Exceptional cross-functional collaborator.
- High ownership mindset with bias for action.
- Strong communication skills with executive presence.
- Passion for building inclusive, high-performing teams.
Why This Role Matters:
Money is foundational to our platform and our customers’ success. This leader will shape the systems that power how businesses and individuals manage, move, and understand their money—ensuring trust, reliability, and innovation at scale.
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. Please review our Fraudulent Activity Disclaimer.
Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.
Top Skills
Gusto New York, New York, USA Office
Located in the heard of midtown, Penn 1 is redefining what it means to work in the Penn District. Gusto's 52nd Floor office boasts amazing views of the city and is centrally located with access to subways, LIRR, and buses, while some Gusties also bike to work!
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