Why This Job is Featured on The SaaS Jobs
This Head of Engineering remit sits at the intersection of SaaS and embedded financial infrastructure, where product reliability and platform correctness directly shape customer trust. The listing signals a mature, high-usage environment within a payroll and fintech platform, with responsibilities spanning core payments foundations and the product surfaces built on top of them. In the SaaS ecosystem, roles like this are notable because they combine platform stewardship with business-critical outcomes rather than isolated feature delivery.
For a long-term SaaS engineering career, leading a large, multi-layered organization around a foundational platform builds durable leadership leverage. The work implies experience modernising architectures, setting technical direction across multiple teams, and partnering closely with product and design to translate complex domain constraints into scalable systems. Those are transferable skills for senior roles in subscription businesses that depend on uptime, compliance, and predictable execution across a roadmap.
This role tends to suit senior engineering leaders who are comfortable operating across strategy and deep technical detail, and who enjoy developing other leaders at scale. It also fits professionals motivated by operational rigor and by building platforms that other teams rely on, where prioritisation, risk management, and cross-functional alignment are daily requirements.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
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
You will lead a large, multi-layered engineering organization responsible for the foundational pillar of Gusto’s business - our fntech platform and products. 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.
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 to be more scalable, reliable, and flexible 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.
Here’s what we're looking for:
- A seasoned engineering leadership background with 15+ years in the industry and 7+ years leading multiple teams and other People Empowerers in a senior leadership capacity.
- A proven ability to scale and lead large organizations, with direct experience managing engineering teams of 50-100+ people, including developing other leaders and principal-level engineers.
- Deep technical credibility and a hands-on approach, with the ability to dive into the details of system architecture, design, and code when needed.
- Experience leading mature, at-scale products, with a demonstrated ability to balance long-term strategic investments with short-term business impact.
- A strategic mindset for platform modernization, with demonstrated success leading teams through the evolution of legacy systems into modern, service-oriented architectures.
- A passion for building exceptional teams and a strong track record of hiring, coaching, and retaining top-tier, diverse engineering talent.
Compensation:
Our cash compensation amount for this role is targeted at $214,000-$264,000 /yr in Denver & most remote locations, and $251,000-$309,000 /yr for San Francisco & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.
