Head of AI and Machine Learning Engineering

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy . AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About the Role: 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…