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:

The Engineering Manager, Payroll Canada role is a foundational position on Gusto’s vanguard Payroll Canada team — a small, mission-driven group building the next evolution of Gusto’s payroll engine for a new market.

As the People Engineering (PE) leader for Payroll Canada, you’ll lead and grow a talented team of engineers who are architecting and building the systems that power Canadian payroll from the ground up. You’ll set the technical direction, ensure alignment across product and operations partners, and foster an environment where engineers can do the best work of their careers.

This role blends hands-on technical leadership, people management, and strategic influence. You’ll guide your team through complex, high-impact work — ensuring accuracy, compliance, and scalability — while shaping how Gusto’s payroll platform evolves to support new countries and markets.

This is a rare opportunity to lead at the intersection of technical vision, product impact, and team growth — helping define the future of Gusto’s global payroll platform while empowering your team to build systems that truly matter.

About the Team:

The Payroll Canada team is part of Gusto’s broader Payroll organization, which builds the core systems that ensure people get paid accurately and on time — every time. Our mission is to bring Gusto’s trusted payroll experience to Canada, crafting a platform that’s compliant, reliable, and delightful for employers and employees alike.

You’ll join a tight-knit, multidisciplinary team of engineers, product managers, designers, and operations experts united by a shared goal: to design and deliver payroll for Canada with the same simplicity and care that define Gusto’s products today. The work is both deeply technical and deeply human — requiring architectural foresight, cross-functional collaboration, and empathy for customers and teammates alike.

Here’s what you’ll do day-to-day:

• Lead and grow a team of software engineers, fostering a culture of technical excellence, ownership, and inclusion.
• Set technical direction for Gusto’s Canadian payroll systems — architecting APIs, services, and data models that scale from early pilots to a multi-country platform.
• Drive execution of complex, cross-functional initiatives from inception to production, ensuring systems are correct, compliant, and resilient under load.
• Collaborate closely with Product, Design, and Operations partners to shape the customer experience for Canadian payroll, balancing speed with long-term scalability.
• Mentor engineers through thoughtful feedback, design reviews, and hands-on guidance — helping them grow technically and professionally.
• Promote engineering excellence through best practices in testing, observability, performance, and maintainability.
• Build strong partnerships across Gusto’s R&D and operations organizations, ensuring alignment on technical strategy and execution.
• Influence global payroll evolution, contributing to Gusto’s long-term strategy for scaling payroll systems to new markets.

Here’s what we're looking for:

• 8+ years of experience in software engineering, with a proven record of driving IC-level impact through technical direction and execution on complex, distributed systems.
• 2+ years of full-time experience as an Engineering People Manager or PE, leading product engineering team(s).
• Proven success building or modernizing high-availability, transactional, or compliance-critical systems, ideally (though not required) within payroll, fintech, or tax domains.
• Deep experience designing APIs, data models, and customer-facing experiences that perform reliably at scale.
• Demonstrated ability to lead cross-functional technical initiatives from inception to production, balancing speed, quality, and operational excellence.
• Experience working with systems that integrate third-party APIs, handle sensitive financial data, or require high auditability.
• Strong track record of mentoring senior engineers, influencing system design beyond direct ownership, and establishing engineering best practices.
• Comfortable operating across infrastructure and product layers — from backend logic to orchestration, observability, and deployment.
• Proven ability to build and sustain high-performing teams, fostering trust, collaboration, and a sense of shared purpose.
• Bonus experience with global payroll, multi-currency systems, or region-specific compliance frameworks.
• Bonus experience with Kafka, event-driven architectures, or distributed data consistency models.
• Bonus familiarity with Ruby on Rails or similar web frameworks.
• End-to-end systems thinker who understands the interconnected nature of payroll systems — from compliance logic and data pipelines to product workflows and customer experience.
• Technical visionary and hands-on builder who combines architectural foresight with deep implementation experience.
• Champion of engineering excellence who sets a high bar for code quality, testing rigor, and observability.
• Master executor in ambiguous domains who thrives in “0→1” environments and drives clarity through complexity.
• Cross-functional collaborator and influencer who builds strong, trust-based relationships with Product, Design, Ops, and CX partners.
• Builder of scalable foundations who recognizes patterns that generalize across regions to enable future growth.
• Cultural contributor and mentor who leads by example and fosters a culture of curiosity, ownership, and inclusivity.