Staff Product Manager

Join Guesty, a leading property management platform, as a Staff Product Manager. In this role, you will lead cross-domain AI and strategic product initiatives, co-shape the AI product strategy, and drive AI adoption within the product department. You will have hands-on experience with AI building and will be a trusted voice on AI product judgment. The ideal candidate will have 8+ years of product management experience, including 2+ years focused on AI/LLM-powered products, and a track record of leading large cross-domain initiatives.

• Lead cross-domain AI and strategic product initiatives, driving impactful AI projects end-to-end.
• Co-shape the AI product strategy, partnering closely with product leaders to define the roadmap and outcomes.
• Prototype with AI hands-on, building agents, workflows, and internal tools to enhance productivity across the product organization.
• Excellent verbal and written communication skills in English (mandatory)
• Proven ability to drive strategic initiatives end-to-end — from shaping which problems matter, through stakeholder alignment, to accountable delivery of outcomes
• Excellent product craft and data fluency: discovery, specs, metrics definition and interpretation against business goals — and the judgment to know when a demo is a product and when it isn't
• Executive presence: Demonstrated experience aligning executive management and communicating complex, ambiguous topics clearly
• AI-native, hype-resistant judgment: You understand the difference between a RAG pipeline and an agentic loop, you think about reliability, latency, and cost — not just model brilliance — and you prefer building things that actually work over things that just look cool in a demo
• Hands-on AI building experience: You've shipped AI-powered product features to production and you build with LLMs yourself — prompting, evals, agent frameworks, and rapid prototyping are part of your daily toolkit, not something you delegate. You don't wait for a system to exist before creating one
• 8+ years of product management experience, including 2+ years focused on AI/LLM-powered products, and a track record of leading large cross-domain, cross-team initiatives through influence rather than authority
• Experience mentoring PMs and reviewing their work — you raise the bar around you
• Experience in B2B SaaS platforms, marketplaces, or the hospitality/travel tech space
• Experience driving internal AI adoption or AI enablement programs within a product or R&D organization