Software Engineering Manager, Gusto
Payroll Canada
$163-247k
Salary dependent on location. Salary benchmarked in USD rates and may differ on location + Equity
2-3 days a week in office
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$163-247k
Salary dependent on location. Salary benchmarked in USD rates and may differ on location + Equity
2-3 days a week in office
1001+ employees
Company mission
To create a world where work empowers a better life.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 200,000 customers and a multi-billion dollar valuation. In 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that will see it reach key profitability benchmarks. It continues to consolidate its platform, for example by integrating with OpenComp to grant its users access to the company's Compensation Intelligence Platform.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Comprehensive medical, dental, and vision benefits, plus a variety of mental health resources
- Flexible vacation - Gusties are encouraged to take the time off they need to continue doing great work
- Fertility treatments, parental leave, pregnancy termination, caregiving, gender-affirming surgery, hormone treatments, transgender-inclusive services, and more
- If you work at one of our homebases, enjoy food, drinks, and good conversation — on us
- Celebrate 5 or 10 years at Gusto and take a month off to recharge
- Take advantage of internet, phone, commuter, and wellness stipends each month, along with a WFH stipend and cash for anniversaries
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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