Head of AI and Machine Learning Engineering

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.

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.