Senior Product Manager AI

About the Senior Product Manager AI Role at Hostaway

Hostaway is a profitable, high-growth SaaS startup revolutionizing the vacation rental industry, recognized as the first short-term rental Property Management System unicorn. As a Senior Product Manager AI, you will be instrumental in shaping how Hostaway AI assists, augments, and automates various aspects of property management. This role focuses on streamlining routine work, elevating decisions with insights, and simplifying complex tasks to unlock new revenue opportunities, boost operational efficiency, and improve customer satisfaction across the property management lifecycle.

You will define and execute the strategy for our AI product to serve our core users—property managers, owners, and cleaners—while partnering closely with engineering, design, and marketing to deliver seamless, intuitive AI-driven user experiences. Success in this role requires deep customer empathy and hands-on involvement in user research, ensuring we solve real pain points without unnecessary complexity.

Key Responsibilities

• Drive outcomes and own results for a multi-million dollar business line.
• Help develop and implement the Hostaway AI vision, strategy, and roadmap, breaking it down into rapidly shippable projects consistent with the company vision.
• Collect and analyze customer, stakeholder, and team feedback to shape requirements, features, and end products.
• Collaborate with senior management to create product plans and roadmaps, based on customer interaction and aggregated feedback.
• Partner with sales, customer success, and engineering to deliver features and products that effectively solve user problems.
• Ensure products and releases are launched correctly and on schedule.
• Define and analyze key metrics to determine product success.
• Make creative recommendations to expand the product base and vision, actively seeking opportunities for innovation.

What You Will Bring

• 5+ years of product management experience, ideally in B2B/B2C SaaS.
• Strong understanding of AI/ML fundamentals to evaluate feasibility with engineers (this is not a data scientist role).
• Solid grasp of Large Language Models (LLMs), including prompt design and evaluation, managing quality and risk, and awareness of model capabilities, costs, latency, and context limits.
• Experience assessing and integrating off-the-shelf AI solutions, including LLMs, APIs, SaaS AI services, and third-party ML products.
• Strong understanding of agentic AI concepts (tool use, planning, orchestration).
• Deep empathy for users, thinking in terms of workflows, friction points, and moments of delight, with hands-on involvement in user research.
• Ability to make decisions effectively amidst uncertainty, without requiring constant support.
• Capacity to lead by influencing without authority, aligning cross-functional teams around clear goals, and driving outcomes through trust, clarity, and data-informed decision.

What Success Looks Like

• AI-powered features are seamlessly embedded into Hostaway’s SaaS product.
• Customer workflows become smarter, faster, and more personalized due to your team's integrations.
• AI services are stable, observable, and easy to maintain.
• You become the go-to person for the Hostaway AI product vision and capabilities across the company.

What Hostaway Offers

• Competitive Compensation: Market-rate pay based on your country of residence within EMEA.
• 100% Remote: Full flexibility to work from anywhere in your country of residence within EMEA.
• Equity: Valuable stock options in a fast-growing, profitable company.
• Values-Driven Leadership: A culture where core values guide daily strategic and tactical decisions.
• Professional Growth: Unparalleled learning, development, and career advancement opportunities.
• Annual Paid Leave: Aligned with country and contract-specific norms.
• Geographic Specific Benefits: Health Insurance and Pensions offered in countries where customary.
• Dynamic Team Culture: A diverse and international team spanning over 40 countries, fostering innovation and creativity.

Key skills/competency

• Product Management
• AI/Machine Learning
• SaaS B2B/B2C
• LLMs (Large Language Models)
• Prompt Engineering
• User Research
• Product Strategy
• Cross-functional Leadership
• Roadmap Development
• Agentic AI