Staff Product Manager – AI

🕒 June 1

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Hostaway

WebsiteLinkedInAll Job Openings

51 - 200 employees

☁️ SaaS

🏠 Real Estate

SaaS • Travel • Real Estate

Hostaway is a comprehensive vacation rental management software that assists property managers in streamlining and automating every aspect of their business. Founded in 2015, the company offers a range of features to enhance property management efficiency, including channel management, automated messaging, dynamic pricing, and financial tracking. Hostaway integrates with major online travel agencies like Airbnb, Vrbo, and Booking. com, and provides a centralized dashboard for managing bookings, guest communications, and operations. Known for its robust API, Hostaway enables custom integrations and is trusted by thousands of property managers globally. It boasts award-winning 24/7 customer support and a suite of tools designed to scale with businesses from a few to thousands of listings. Hostaway is ideal for vacation rental managers looking to expand their reach, increase bookings, and optimize their property management processes.

📋 Description

• Own the strategy and roadmap for Hostaway's AI foundations, and evolve them as the AI landscape changes. • Run continuous discovery across technical and product stakeholders to identify where shared investments will create the most leverage. • Stay deeply connected to property manager workflows so that investments translate into real customer and business outcomes. • Shape the capabilities that underpin AI development at Hostaway, across areas such as model access, prompting, retrieval, agents, safety, observability, and cost. • Establish how AI quality is measured and improved over time, including evaluation approaches, benchmarks, and feedback loops. • 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. • Define and track the success metrics that matter, including adoption, customer outcomes, cost, quality, reliability, and scalability. • Influence senior stakeholders and cross-functional leaders to align on AI priorities, tradeoffs, and investments.

🎯 Requirements

• 7+ years of product management experience, ideally in SaaS, including ownership of complex and ambiguous product areas. • Proven experience shaping strategy beyond a single feature or team, ideally across multiple products or a company-level domain. • Strong practical understanding of LLMs and AI product development, including prompting, model tradeoffs, latency, cost, context limits, and quality risks. • Experience defining and using evaluation sets, quality benchmarks, and feedback loops for AI-powered products. • Experience with agentic AI concepts, including tool use, planning, and orchestration. • Experience evaluating and integrating off-the-shelf AI solutions, including APIs, SaaS tools, and third-party platforms. • Highly data-driven, with strong judgment in using metrics, experiments, and customer insight to make decisions. • Demonstrated AI-native curiosity and fluency, with a clear habit of staying current as models, tools, and best practices evolve.

🏖️ Benefits

• Competitive Compensation: We offer competitive pay based on market rates in the country of the applicant. • 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. • Equity: Every role in our company comes with valuable stock options in a fast-growing and profitable company. • Values-Driven Leadership: Our Core Values are not just words we’ve written to make us feel good. • Professional Growth: Our rapid growth offers unparalleled learning and development opportunities. • Annual Paid Leave: The specific amounts vary by country and are aligned with country and/or contract-specific norms. • 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. • Dynamic Team Culture: As a global company with team members in over 40 countries, our diverse and international culture fuels our innovation and creativity.