Head of AI and Machine Learning Engineering

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.

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. Your teams will help translate business problems into end-to-end AI/ML systems, from experimentation and prototyping through evaluation, deployment, monitoring, feedback loops, and operational governance.

Your leadership will be critical in setting the technical direction, operating model, and quality bar for AI at Gusto. You will help teams move quickly where speed and learning matter most, while ensuring production systems meet high standards for reliability, measurement, safety, and long-term maintainability. This is a senior technical executive role for someone who can combine deep engineering credibility, strong business judgment, and executive-level influence to make AI a durable advantage for Gusto.

• 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.

Our cash compensation amount for this role is targeted at $275,000-305,000 in Denver & most remote locations, and $320,000-350,000 for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

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