Head of AI Transformation

Description Guesty is the all-in-one platform helping hospitality businesses around the world automate, optimize, and scale their operations. We’re a fast-growing global startup that’s transforming how the industry works — from guest experience to business growth. With a powerful suite of features and integrations with 150+ industry partners — including Airbnb, Vrbo, Booking.com, Expedia, Google Travel, and many more — Guesty empowers property managers to deliver top-tier guest experiences while running more efficient, data-driven operations. We’re proud to have over 900+ team members across 16 countries worldwide, all working together to build the future of hospitality technology. If you’re looking to grow your career in a dynamic, global, and impact-driven environment, we’d love to hear from you. We are looking for a Head of AI Transformation to lead the team that changes how Guesty operates with AI, across every department. You will own the roadmap, run the AI team, and work with department leaders to move work from people to automation and agents, with measurable results. The role has two parts. First, you are the glue for cross-department projects that no single department owns end to end. Second, you build the infrastructure, standards and enablement that let each department automate and build on its own. This is a leadership role with a hands-on edge: you stay close enough to the tools to judge what is good, and you build when it matters. Responsibilities Strategy and results: • Define and own the company AI transformation roadmap, and tie each department's plan to measurable KPIs (hours saved, workload automated, cost avoided, revenue impact). • Report progress to senior leadership: what shipped, what it delivered, and what comes next. • Decide where AI should and should not be used, balancing speed, cost, risk and quality. Delivery across departments: • Lead cross-department AI projects end to end, from identifying the opportunity to production and adoption. • Work with department heads and AI champions to find the highest-impact use cases, and embed AI transformation managers in the departments that need them. • Move teams up the maturity curve, from using AI tools to running autonomous, agent-based workflows. Platform and infrastructure: • Own the internal AI infrastructure that departments build on: our automation and agent platforms, internal AI tools, shared knowledge and data access, and the standards around them. • Evaluate and adopt new technologies (n8n, Claude and Claude Code, Google's agent platform, AWS AgentCore and more) and decide what we build, buy or retire. • Set governance for security, data access, quality, monitoring and ownership of automations, so that non-technical builders can work safely. • Manage the AI tooling and inference budget. Enablement: • Grow builders inside the business: training, templates, office hours and clear guidelines that let teams build and maintain their own automations. • Share what works across the company and turn successful internal tools into reusable solutions. Team: • Lead, coach and grow the AI team: AI transformation managers and AI engineers, across locations. • Set priorities, run the weekly rhythm, and hold the team to delivery and impact. • Build selected solutions yourself, enough to stay technically credible and unblock the team. Requirements Technical and professional expertise • 8+ years of experience in automation, business transformation or operations, including 3+ years managing a team. • Proven track record of delivering AI-driven automation and agent-based solutions in production, with measurable business impact. • Hands-on experience with automation and agent tooling such as n8n, Make, Claude / Claude Code, and cloud agent platforms (Google, AWS AgentCore or similar). • Experience leading business or operational transformation across several departments, including influencing leaders you do not manage. • Data-driven approach: you define KPIs, measure results and know when something is not working. • Solid understanding of AI risks and governance: security, data privacy, hallucinations, quality and cost. Leadership and mindset • Experience managing and growing multidisciplinary teams, ideally a mix of business-facing and technical people. • Ability to work with senior leadership and present to the C-level. • Comfortable in a fast-paced environment with many priorities and an area that changes every month. • Tech-savvy, with the credibility to go deep on a workflow with a builder and step back to the business case with an executive. • Fluent in English and strong communication skills. Bonus Points • Experience in hospitality, hotels, travel or property management. • Experience at a global B2B SaaS company. • Background in customer experience, operations or BI. • Experience with LLM and agent architectures, evaluation and observability. Guesty is proud to be an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.