Head of AI Engineering

Remote, United States

JOB OVERVIEW

We are seeking a forward-looking and deeply technical Head of AI Engineering to lead all AI initiatives at Legion. This executive will oversee the AI Engineering organization—including both our applied ML and data science functions—and be responsible for driving innovation across traditional and generative AI domains. This role is critical to shaping Legion’s product strategy, internal development practices, and long-term AI vision.

The ideal candidate combines deep technical expertise with strong organizational leadership and has a passion for applying AI to real-world enterprise challenges.

RESPONSIBILITIES AND DUTIES

1. Scale and Mature Traditional AI Capabilities

• 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.

2. Define and Build Generative AI Experiences

• 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.

3. Drive AI-Enabled Transformation Across Engineering

• 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.

4. Own Data Science and Applied Research

• Oversee a cross-functional team of data scientists, ML engineers, and research specialists.
• Foster a culture of experimentation, responsible AI practices, and measurable impact.

5. Evangelize AI Vision and Practices

• 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.

REQUIRED SKILLS AND QUALIFICATIONS

• 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.

PREFERRED QUALIFICATIONS AND ATTRIBUTES

• 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.

COMPENSATION & BENEFITS

Salary Range: Base Salary Range $200,000 - $300,000 + Bonus + Stock Equity

At Legion, we offer competitive compensation and benefits packages to all employees. As a fully remote employer, pay for positions is determined using local, national, and industry-specific survey data. 

Our posted salary range is done so in good faith based on national data and may be refined for a candidate's region/town/cost of living. We strive to make competitive offers allowing employees room for future growth. Salaries will be based on the applicant’s location, level of experience, education, and specialized knowledge and skills. Additionally, we consider the external market rate, the amount we have budgeted internally, and internal equity within the company for the same position. 

Benefits include, but are not limited to:

• $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

ABOUT LEGION

Join Legio