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 Legion's mission to turn hourly jobs into good jobs. We're a remote, mission-driven team seeking exceptional talent to propel this vision. Embrace a culture that's collaborative, fast-paced, and entrepreneurial. With us, you'll grow your skills, work closely with experienced executives, and contribute significantly to our mission. Our award-winning AI-native workforce management platform is intelligent, automated, and employee-centric and has proven to deliver 13x ROI. We help labor-intensive organizations maximize labor efficiency and employee engagement simultaneously. Legion has earned recognition for its innovation, including spots on the Inc. 5000 list, Forbes’ Next Billion Dollar Startups, and awards for our AI technology. Backed by leading investors such as Norwest Venture Partners, Stripes, First Round Capital, XYZ Ventures, Webb Investment Network, Workday Ventures, and NTT DOCOMO Ventures, we're making real change.

If you're ready to make an impact and grow your career, Legion is where you belong. Join us in making hourly work rewarding and fulfilling.

BACKGROUND AND OPPORTUNITY 

There are almost 75 million hourly workers in the United States, representing more than half of the entire workforce. Historically, managing hourly employees has been difficult due to high attrition (average of 60%) and high replacement costs (average of $3,200 per employee in retail). The ongoing labor shortage and competition from the gig economy, make it more difficult to attract and retain hourly employees. The top reasons hourly employees leave their jobs are a lack of schedule empowerment, poor communication with employers, and an inability to get paid early. Gen Z and the millennial workforce demand gig-like flexibility, modern technology, and compelling work options. Legion’s mission is to turn hourly jobs into good jobs, serving the hourly workers who make up the majority of the US workforce. We believe in empowering employees and helping employers be efficient and innovative by enabling intelligent automation powered by Legion’s Workforce Management platform to optimize labor efficiency and enhance the employee experience simultaneously. Legion WFM was built for the cloud with AI at the core and designed to handle the complexity of modern businesses and meet the needs of today’s hourly employees.  Our team is comprised of dedicated individuals from all backgrounds and experiences, globally distributed across all time zones.

For more information, visit https://legion.co 

EQUAL EMPLOYMENT OPPORTUNITY

Legion Technologies is proud to be an equal-opportunity employer and is committed to maintaining a diverse and inclusive work environment. All qualified applicants will be considered for employment without regard to race, color, religion, sex, age, disability, marital status, familial status, sexual orientation, pregnancy, genetic information, gender identity, gender expression, national origin, ancestry, citizenship status, veteran status, and any other legally protected status under federal, state, or local anti-discrimination laws.

DISABILITY ACCOMMODATION

For individuals with disabilities who need additional assistance at any point in the application and interview process, please email recruiting@legion.co