Head of AI and Machine Learning Engineering

About the Role:

Gusto is looking for a strategic Head of AI/MLE to lead its next chapter in leveraging AI and ML to improve customer experiences, automate complex work, support better decision-making, and help small businesses thrive. This role involves defining how Gusto builds, deploys, evaluates, and scales AI/ML systems across the company. You will lead a broad organization encompassing Machine Learning Engineering, ML Platform, Risk Data Science, and AI Scientists, collaborating closely with senior business leaders to identify impactful applications of AI.

As the Head of AI/MLE, you will unify classical ML and GenAI into a coherent technical strategy, mature the platform for broader self-service adoption, and shape how AI-native products and production systems are built. Your teams will translate business problems into end-to-end AI/ML systems, covering experimentation, prototyping, evaluation, deployment, monitoring, feedback loops, and operational governance. This senior technical executive role requires deep engineering credibility, strong business judgment, and executive-level influence to establish AI as a durable advantage for Gusto.

Here’s what you’ll do day-to-day:

• 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.

Here’s what we're 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.