NOTE: This is a FULLY remote role, but the candidate must be within EMEA to collaborate with their team, peers, and internal customers. You do not have to be in the specific country or city shown in this listing, but please only apply if you are physically based within EMEA.
Trusted by 20,000+ property managers worldwide, Hostaway is an industry leading, AI-powered vacation rental management platform designed for professional short-term rental operators. Hostaway brings everything together for greater efficiency and faster growth.
Profitable, high-growth, and the first short-term rental Property Management System unicorn . Join us at our most exciting stage yet! Learn more about our recent valuation and story here.
Hostaway AI creates value by streamlining routine work, improving decision-making, and simplifying complex tasks across the property management lifecycle. As Staff Product Manager, AI, you will define and own the strategy and roadmap for the foundations that AI-driven experiences are built on at Hostaway.
You will shape and evolve the foundations that AI development at Hostaway is built on, working across teams rather than owning a single product surface. Success in this role requires a deep understanding of both technical foundations and end-customer needs, because the work only matters if it translates into measurable value for property managers.
This role is for an AI-native product leader who combines strong product judgment, customer empathy, analytical rigor, and a developer-experience mindset. You do not need to build AI models yourself, but you must understand how LLM-based products work in practice, how to evaluate them with discipline, and how to translate a rapidly evolving AI landscape into clear decisions and reliable building blocks.
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Own the strategy and roadmap for Hostaway's AI foundations, and evolve them as the AI landscape changes.
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Run continuous discovery across technical and product stakeholders to identify where shared investments will create the most leverage.
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Stay deeply connected to property manager workflows so that investments translate into real customer and business outcomes.
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Shape the capabilities that underpin AI development at Hostaway, across areas such as model access, prompting, retrieval, agents, safety, observability, and cost.
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Establish how AI quality is measured and improved over time, including evaluation approaches, benchmarks, and feedback loops.
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Drive build vs. buy decisions across LLMs, APIs, and AI tooling, integrating best-in-class solutions where they fit and building only where it creates durable advantage.
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Define and track the success metrics that matter, including adoption, customer outcomes, cost, quality, reliability, and scalability.
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Influence senior stakeholders and cross-functional leaders to align on AI priorities, tradeoffs, and investments.
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7+ years of product management experience, ideally in SaaS, including ownership of complex and ambiguous product areas.
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Proven experience shaping strategy beyond a single feature or team, ideally across multiple products or a company-level domain.
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Strong practical understanding of LLMs and AI product development, including prompting, model tradeoffs, latency, cost, context limits, and quality risks.
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Experience defining and using evaluation sets, quality benchmarks, and feedback loops for AI-powered products.
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Experience with agentic AI concepts, including tool use, planning, and orchestration.
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Experience evaluating and integrating off-the-shelf AI solutions, including APIs, SaaS tools, and third-party platforms.
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Highly data-driven, with strong judgment in using metrics, experiments, and customer insight to make decisions.
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Demonstrated AI-native curiosity and fluency, with a clear habit of staying current as models, tools, and best practices evolve.
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AI-powered features are seamlessly embedded into Hostaway’s SaaS product.
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Customer workflows feel smarter, faster, and more personalized thanks to the integrations you build with the team.
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AI services are stable, observable, and easy to maintain.
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You become the go-to person for the Hostaway AI product vision and capabilities across the company.
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Competitive Compensation: We offer competitive pay based on market rates in the country of the applicant.
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100% Remote: Enjoy the freedom to work from anywhere within your country of residence—be it a co-working space, your home office, or even your dining room table. The choice is yours. Just don’t ask to work in our office (we don’t have one).
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Equity: Every role in our company comes with valuable stock options in a fast-growing and profitable company. This ensures we all share in the company’s success.
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Values-Driven Leadership: Our Core Values are not just words we’ve written to make us feel good. We leverage them daily when making strategic and tactical decisions.
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Professional Growth: Our rapid growth offers unparalleled learning and development opportunities, along with a multitude of career advancement opportunities.
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Annual Paid Leave: The specific amounts vary by country and are aligned with country and/or contract-specific norms.
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Geographic Specific Benefits: As an international employer, we offer different country-specific benefits such as Health Insurance and Pensions in countries where these perks are customary. The specifics depend on the country of the applicant.
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Dynamic Team Culture: As a global company with team members in over 40 countries, our diverse and international culture fuels our innovation and creativity, providing a key pillar to our success (and making it a lot of fun to work here).
Thank you for your interest. If you apply for this role, you will receive an email from our Talent Acquisition team after your application has been reviewed alongside the qualifications for this role and the qualifications of others who have applied.
