Head of AI & ML Engineering, Gusto
$275-350k
+ RSUs. Salary is benchmarked against US rates and is dependent on location
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$275-350k
+ RSUs. Salary is benchmarked against US rates and is dependent on location
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- This is a senior technical executive role for someone who can combine deep engineering credibility, strong business judgment, and executive-level influence to make AI a durable advantage for Gusto
- We love meeting people with different technical and leadership backgrounds. For this role, we are looking for 10+ years of experience leading teams in applied machine learning, AI, engineering, or data science roles, with a track record of delivering impactful customer-facing software solutions
- Deep technical expertise across AI/ML systems, including classical ML, GenAI/LLMs, statistical modeling, risk modeling, and production-scale deployment
- Strong software engineering and systems background, with the ability to lead technical strategy across data, retrieval, evaluation, deployment, routing, monitoring, observability, feedback loops, and lifecycle management
- Experience leading and scaling high-performing technical organizations, including Machine Learning Engineers, AI/ML Platform teams, Risk Data Scientists, and/or AI Scientists
- Experience evolving ML teams toward a stronger software engineering and systems orientation, with clear ownership for building, operating, and improving production AI/ML systems
- Strong platform orientation, with experience building tools, primitives, guardrails, and self-service capabilities that help product and engineering teams build AI/ML-powered products safely and effectively
- Executive-level strategic judgment, with the ability to shape company-level AI/ML priorities, align senior leaders around tradeoffs, and make clear investment decisions based on customer value, business impact, technical feasibility, risk, data readiness, and operational complexity
- Strong executive communication and influence, with the ability to explain complex AI/ML concepts and technical decisions in a way that clarifies strategy, tradeoffs, risk, investment needs, and organizational implications
- Experience operating as a peer to senior cross-functional leaders across product, engineering, design, data, risk, legal, security, and business teams — bringing clarity, urgency, and practical judgment to ambiguous company-level opportunities
- A clear thesis on how classical ML and GenAI should work together, how modern AI platform capabilities like retrieval, evaluation, agents, and observability should come together, and how AI/ML teams should evolve as the field becomes more software- and systems-oriented
- Experience in fintech, risk modeling, regulated environments, or domains with high standards for reliability, trust, and compliance is a plus
- Advanced degree in computer science, data science, machine learning, statistics, or a related field is a plus, but demonstrated systems leadership, production judgment, and executive-level impact matter most
What the job involves
- Gusto sits at the center of many of the most important workflows for small businesses, which creates a meaningful opportunity to use rich product and customer data to build AI- and ML-powered systems that improve customer experiences, automate complex work, support better decision-making, and help small businesses thrive
- As Gusto becomes more AI-native, we are evolving how AI, ML, risk modeling, and platform capabilities come together across our products and internal systems
- We are seeking a strategic Head of AI/MLE to lead this next chapter. In this key leadership role, you will define how Gusto builds, deploys, evaluates, and scales AI/ML systems across the company
- You will lead a broad organization spanning Machine Learning Engineering, ML Platform, Risk Data Science, and AI Scientists, while partnering closely with senior business leaders to shape where AI can create durable customer and business impact
- As the Head of AI/MLE at Gusto, you will be responsible for unifying classical ML and GenAI into a coherent technical strategy, maturing the platform for broader self-service adoption, and shaping how AI-native products and production systems are built at Gusto
- Your teams will help translate business problems into end-to-end AI/ML systems, from experimentation and prototyping through evaluation, deployment, monitoring, feedback loops, and operational governance
- Your leadership will be critical in setting the technical direction, operating model, and quality bar for AI at Gusto
- You will help teams move quickly where speed and learning matter most, while ensuring production systems meet high standards for reliability, measurement, safety, and long-term maintainability
- Lead, manage, and develop a broad AI/MLE organization spanning Machine Learning Engineering, ML Platform, Risk Data Science, and AI Scientists, fostering a culture of technical excellence, customer impact, collaboration, and continuous learning
- Define and execute Gusto’s AI/ML systems strategy, unifying classical ML, GenAI, risk modeling, and platform capabilities into a coherent approach that supports Gusto’s broader business and product goals
- Partner with senior leaders across Product, Engineering, Design, Data, Risk, Legal, Security, and business teams to identify where AI/ML can create meaningful customer value, business impact, and operational leverage
- Shape how AI-native products and internal systems are built at Gusto, helping teams translate business problems into end-to-end AI/ML systems with clear standards for evaluation, monitoring, observability, reliability, safety, governance, and long-term maintainability
- Lead the development and maturation of AI/ML platform capabilities, tooling, primitives, guardrails, and deployment patterns that make it easier for product and engineering teams to build, evaluate, deploy, and operate AI/ML systems with less friction, more autonomy, and the right quality bar
- Drive disciplined technical and business judgment around AI/ML investments, including where to build, where to leverage existing capabilities, and where to avoid unnecessary complexity
- Create room for fast experimentation and learning where appropriate, while ensuring high-impact production systems meet strong standards for quality, operational rigor, and business accountability
- Set clear goals, KPIs, and operating rhythms to measure the performance, adoption, and business impact of AI/ML systems, and communicate progress and tradeoffs clearly to senior leadership
- Stay close to the frontier of AI/ML advancement and help Gusto apply new technologies pragmatically, with strong judgment about what is durable, useful, and ready for production
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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