Head of AI and Machine Learning Engineering

About the company

• Gusto is on a mission to grow the small business economy, handling payroll, health insurance, 401(k)s, and HR for more than 500,000 small businesses nationwide.
• Teams in Denver, San Francisco, and New York.

About the role

• We are seeking a strategic Head of AI/MLE to lead this next chapter, defining 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.

Responsibilities

• Lead, manage, and develop a broad AI/MLE organization, fostering a culture of technical excellence and continuous learning.
• Define and execute Gusto's AI/ML systems strategy, unifying classical ML, GenAI, risk modeling, and platform capabilities.
• Partner with senior leaders across Product, Engineering, Design, Data, Risk, Legal, Security, and business teams.
• Shape how AI-native products and internal systems are built, with clear standards for evaluation, monitoring, observability, reliability, safety, governance, and maintainability.
• Lead the development and maturation of AI/ML platform capabilities, tooling, primitives, guardrails, and deployment patterns.
• Set clear goals, KPIs, and operating rhythms to measure performance, adoption, and business impact.

Requirements

• 10+ years of experience leading teams in applied machine learning, AI, engineering, or data science roles.
• 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.
• Experience leading and scaling high-performing technical organizations.
• Experience evolving ML teams toward a stronger software engineering and systems orientation.

Conditions

• Hybrid role based in Denver, CO; San Francisco, CA; or New York, NY.