Head of AI

At Winn.ai, AI isn’t a feature, its our core advantage.

We’re continuously advancing our AI capabilities and pushing the boundaries of what’s possible. Now, we’re looking for someone to help us stay at the forefront as the field continues to evolve rapidly.

This role is about ensuring our Product and R&D organization consistently operate at the cutting edge of AI in both what we build and how we build it.

What You’ll Own

You’ll shape how AI capabilities are scaled, integrated, and advanced across the company:

• Own and evolve our LLM strategy selecting the right models, tools, and approaches as the ecosystem evolves
• Shape how AI is built across the company from architectures to pipelines to developer workflows
• Design and refine production-grade AI systems (prompting, RAG, orchestration, pipelines)
• Build evaluation frameworks and feedback loops to continuously improve performance and reliability
• Turn fast-moving AI capabilities into reliable, production-ready features
• Continuously bring new AI advancements into the company and translate them into a competitive advantage
  
  

Requirements:

• Deep hands-on experience with LLMs and modern AI systems
• A systems thinker who looks beyond prompts to full architectures
• A builder mindset you enjoy shipping and learning from real-world usage
• A strong communicator and collaborator who elevates the people around them
• Comfortable operating in fast-moving, ambiguous environments
• Cares deeply about performance, usability, and scale
  
  

Why this role matters

AI is evolving at an unprecedented pace.

This role ensures Winn.ai not only keeps up but stays ahead by continuously integrating new capabilities into our product and development workflows, and reinforcing our position at the leading edge of applied AI.

You won’t be starting from scratch. You’ll be accelerating something that’s already working and helping define what it becomes next.

WINN.AI is committed to diversity, equity, and inclusion, and we want teammates who are similarly passionate about pushing for change in our industry.

If you have reached this point and you are super excited but not sure you check all the boxes - we still want to speak with you! Your passion is priceless. Other things can be learned.

WINN.AI is an Equal Employment Opportunity employer that will consider all qualified applicants, regardless of race, color, religion, gender, sexual orientation, marital status, gender identity or expression, national origin, genetics, age, disability status, protected veteran status, or any other characteristic protected by applicable law.

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