Head of AI Engineering

Summary

Join Legion as their forward-looking Head of AI Engineering, leading all AI initiatives and overseeing the AI Engineering organization, including applied ML and data science. This executive role is crucial in shaping Legion's product strategy, internal development practices, and long-term AI vision. The ideal candidate possesses deep technical expertise, strong organizational leadership, and a passion for applying AI to real-world enterprise challenges. Responsibilities include scaling traditional AI capabilities, defining and building generative AI experiences, driving AI-enabled transformation across engineering, overseeing data science and applied research, and evangelizing AI vision and practices. The position offers a competitive salary and benefits package, including health insurance, retirement plan, paid time off, parental leave, equity, and wellness reimbursements.

Requirements

• 10+ years of experience in AI/ML engineering and data science, with 5+ years in leadership roles
• Proven experience scaling production-grade ML systems and owning the full lifecycle of AI products
• Deep expertise in both traditional ML and modern generative AI technologies (e.g., LLMs, RAG pipelines, embeddings, prompt engineering)
• Strong technical foundation in software engineering and cloud-native architecture
• Ability to lead highly technical teams while collaborating cross-functionally with product, engineering, and go-to-market leaders
• Experience translating complex AI capabilities into customer value
• Excellent communication skills with the ability to influence and align at all levels of the organization

Responsibilities

• Lead continued innovation in Legion’s ML-based forecasting, labor optimization, and demand modeling engines
• Ensure ongoing performance, scalability, and explainability for AI in production across large enterprise deployments
• Support product, sales, and customer success teams on high-impact opportunities where AI drives differentiation
• Own the exploration, prototyping, and launch of generative AI features that transform how users engage with Legion’s platform
• Partner with product, design, and engineering leadership to ensure these features are intuitive, secure, and highly impactful
• Lead internal transformation efforts to embed AI into the software development lifecycle (e.g., AI agents, code generation, automated QA)
• Promote best practices and enablement for AI-first engineering across all product teams
• Oversee a cross-functional team of data scientists, ML engineers, and research specialists
• Foster a culture of experimentation, responsible AI practices, and measurable impact
• Represent Legion’s AI strategy with strategic customers, internal stakeholders, and industry forums as needed
• Serve as a thought partner to the executive team on how AI can accelerate product and company growth

Preferred Qualifications

• Experience in workforce management, enterprise SaaS, or operational technologies
• Experience leading AI innovation in a high-growth or startup environment
• Track record of publishing, contributing to open-source AI projects, or speaking at industry events

Benefits

• $0 monthly premium and other flexible medical, dental, and vision plans are effective on the first day of employment
• 401k plan
• Discretionary Paid Time Off and Paid Holidays
• Parental Leave
• Equity
• Monthly Wellness Reimbursement
• Monthly Lunch at Legion