Gusto, Inc. - Head of ML/AI Engineering

• We love meeting people with different technical and leadership backgrounds. 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. • Executive-level strategic judgment, with the ability to shape company-level AI/ML priorities, align senior leaders around tradeoffs, and make clear investment decisions based on customer value, business impact, technical feasibility, risk, data readiness, and operational complexity. • Strong executive communication and influence, with the ability to explain complex AI/ML concepts and technical decisions in a way that clarifies strategy, tradeoffs, risk, investment needs, and organizational implications. • Experience operating as a peer to senior cross-functional leaders across product, engineering, design, data, risk, legal, security, and business teams — bringing clarity, urgency, and practical judgment to ambiguous company-level opportunities. • A clear thesis on how classical ML and GenAI should work together, how modern AI platform capabilities like retrieval, evaluation, agents, and observability should come together, and how AI/ML teams should evolve as the field becomes more software- and systems-oriented. • Experience in fintech, risk modeling, regulated environments, or domains with high standards for reliability, trust, and compliance is a plus. • Advanced degree in computer science, data science, machine learning, statistics, or a related field is a plus, but demonstrated systems leadership, production judgment, and executive-level impact matter most. • Our cash compensation amount for this role is targeted at $245,000-272,000 in Denver & most remote locations, and $288,000-321,000 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. • 2-3 days • 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.