Head of Engineering, Gusto
Money Group
2-3 days a week in office
Automated payroll, benefits & HR platform
Open for applications
Automated payroll, benefits & HR platform
1001+ employees
Open for applications
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 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
- 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
What the job involves
- 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
- 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
- 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
- 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
- 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
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 400,000 customers and a multi-billion dollar valuation. And 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 has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
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
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & 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
(Co-Founder & 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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