Head of AI Product Strategy

Sky is building the next generation of its Sky OS platform—and AI is becoming a core part of that evolution.

We’re hiring a senior AI Product Leader to own the strategy, execution, and operational leadership of AI-powered features inside Sky OS. This is a product-first, execution-driven role focused on turning AI capabilities into real, reliable, and scalable product outcomes. We are not looking for an AI researcher or model builder. We are looking for a practical AI product leader who understands how to design intelligent workflows, manage AI-driven features, and lead a product function focused on delivery.

Sky has already begun foundational AI work. Your role is to build on that foundation—shaping the roadmap, guiding implementation, and leading the AI product department within an established product framework.

• Own the AI product vision and roadmap for Sky OS
• Translate business and user needs into practical AI-powered features
• Prioritize AI initiatives based on impact, feasibility, and clarity of outcomes
• Operate within—and help mature—the AI product framework already established by the CPO and product team

• Design AI-driven workflows, copilots, and product experiences
• Define how AI should be prompted, guided, and constrained to produce reliable results
• Partner with Engineering to translate product intent into clear execution plans
• Ensure AI features ship, iterate, and improve—not stall as experiments
• Work primarily with Claude (Anthropic) as Sky’s core AI model
• Identify opportunities to improve performance, usability, and outcomes within the existing AI foundation
• Evaluate alternative models or approaches only when a strong, product-driven case exists
• Focus on consistency, predictability, and user trust in AI behavior

• Act as the head of Sky’s AI product department
• Establish clear ownership, prioritization, and delivery standards
• Align Product, Engineering, Design, and Leadership around AI execution
• Help define best practices for AI quality, usability, and reliability

• An AI research or machine learning role
• A “try every new model” or hype-driven AI role
• This role exists to make AI work in production
  .

• 2+ years of experience in Product Management, Product Strategy, or Technical Product Leadership
• Direct experience shipping AI-enabled or AI-assisted products
• Strong understanding of LLMs, generative AI, prompt design, and AI workflows
• Proven ability to turn ambiguous ideas into clear, executable roadmaps
• Comfortable leading a new product function within an existing organization
• Clear communicator who can align technical and non-technical stakeholders
• Lead the applied AI product strategy for a core platform
• Build on an existing AI foundation with executive support
• High-visibility role reporting directly to the Chief Product Officer
• Opportunity to make AI useful, trusted, and durable
  —not experimental

If you’re passionate about practical AI
, strong product execution, and building systems that actually deliver outcomes—we’d love to hear from you.