Head of AI & ML Engineering

Join Gusto, a company dedicated to improving the lives of small businesses. As the Head of AI & ML Engineering, you will lead the development and implementation of AI/ML systems across the company, shaping the future of Gusto's products and internal systems. You will manage a broad organization, partner with senior business leaders, and drive the technical direction and quality standards for AI at Gusto.

• Definir y ejecutar la estrategia de sistemas de IA/ML de Gusto, unificando el aprendizaje automático clásico, GenAI, la modelización de riesgos y las capacidades de la plataforma en un enfoque coherente que apoye los objetivos comerciales y de producto más amplios de Gusto.
• Liderar, gestionar y desarrollar una amplia organización de IA/ML que abarque la ingeniería de aprendizaje automático, la plataforma de ML, la ciencia de datos de riesgo y los científicos de IA, fomentando una cultura de excelencia técnica, impacto en el cliente, colaboración y aprendizaje continuo.
• Colaborar estrechamente con líderes senior de diversas áreas para identificar dónde la IA/ML puede crear un valor significativo para el cliente, un impacto comercial y una ventaja operativa.
• 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
• Experience leading and scaling high-performing technical organizations, including Machine Learning Engineers, AI/ML Platform teams, Risk Data Scientists, and/or AI Scientists
• 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 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
• 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
• 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
• 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 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
• 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
• Experience in fintech, risk modeling, regulated environments, or domains with high standards for reliability, trust, and compliance is a plus
• Deep technical expertise across AI/ML systems, including classical ML, GenAI/LLMs, statistical modeling, risk modeling, and production-scale deployment