Head of Machine Learning and AI

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy. 

About the Role:

Gusto’s Data team harnesses our rich dataset to guide strategic decisions and shape product direction. Operating full-stack, we conduct deep analyses, prototype and deploy predictive models, and build statistical tools that drive value for both internal teams and our customers.

We are seeking a visionary and enterprise-minded Head of Machine Learning and AI to establish and lead Gusto’s ML and AI strategy. Reporting directly to the Head of Data, you will define and drive the strategic agenda for ML and AI, influencing business priorities, shaping product and platform investments, and ensuring advanced data-driven capabilities are a competitive advantage for Gusto.

You’ll partner with senior leaders across Product, Engineering, Design, as well as peers on the Data team, to drive initiatives that transform customer experiences and optimize operations. You’ll also collaborate closely with Platform and Engineering teams to ensure our ML and AI solutions are scalable, robust, and seamlessly integrated.

As the Head of ML/AI, you’ll own the end-to-end lifecycle of ML/AI initiatives—from strategy and opportunity identification to production deployment and performance measurement. Your leadership will be critical in shaping the future of ML/AI within Gusto, setting strategic direction, building a high-performing team of ML/AI practitioners, and driving a culture of responsible innovation.

Here’s what you’ll do day-to-day:

• Define and champion Gusto’s enterprise-wide ML and AI vision and roadmap, aligning initiatives with corporate strategy, customer needs, and long-term business objectives.
• Build, scale, and inspire a world-class ML/AI organization, cultivating senior leadership within the team and fostering a culture of innovation, accountability, and excellence.
• Own the ML/AI portfolio’s strategic planning, resource allocation, and investment decisions, ensuring high-impact delivery and measurable return on investment.
• Guide data-driven strategies across diverse domains — from customer growth and product expansion to operational optimization and risk mitigation — ensuring Gusto scales responsibly while delivering exceptional customer experiences.
• Identify and drive opportunities to build agentic solutions.
• Serve as a strategic partner to Gusto leadership, shaping company priorities and identifying transformational opportunities where ML and AI deliver differentiated customer and business value.
• Drive enterprise-wide adoption of best practices in model development, deployment, monitoring, and lifecycle management, including rigorous approaches to model retraining and MLOps.
• Collaborate closely with Platform and Engineering teams to ensure seamless integration and deployment of models into production environments.
• Advocate for and embed frameworks that ensure fairness, transparency, and accountability in all ML initiatives, championing responsible AI usage throughout the company.
• Establish and track KPIs to measure the performance and business value of ML and AI solutions, reporting results to senior leadership and shaping future roadmaps
• Stay at the forefront of developments in ML and AI, guiding Gusto to remain an industry leader in innovative, data-driven products.

Here’s what we're looking for:

• 10+ years of executive or senior leadership experience leading high-impact ML/AI or data science organizations, with a proven track record of setting enterprise strategy and delivering transformative, scaled solutions.
• Deep expertise in machine learning, statistical modeling, and AI, with a strong track record of leading teams to develop and deploy impactful models at scale.
• Strong understanding of software engineering best practices and scalable system design, with the ability to partner closely with engineering leaders and ensure high standards across ML solutions.
• Exceptional leadership and people management skills; you know how to inspire, motivate, and scale high-performing teams.
• Demonstrated ability to influence execut