Hostaway is a SaaS startup transforming the vacation rental industry; Hostaway AI streamlines routine work, elevates decisions with insights, and simplifies complex tasks.
Senior Product Manager, AI will define and execute the AI product strategy to serve property managers, owners, and cleaners, partnering with engineering, design, and marketing.
Drive outcomes and own results on a multi-million dollar business line; develop and implement Hostaway AI vision, strategy, and roadmap into rapidly shippable projects.
Collect and analyze customer, stakeholder, and team feedback to shape requirements, features, and end products; be directly involved in user research.
Work with senior management to create product plans and roadmaps based on customer interaction and aggregate feedback.
Partner with sales, customer success, and engineering to ship features; ensure products and releases are launched correctly and on schedule.
Define and analyze metrics that determine success; make creative recommendations to expand the product base and vision and actively seek opportunities to innovate.
Requirements
5+ years of product management experience, ideally in B2B/B2C SaaS.
Strong understanding of AI/ML fundamentals to evaluate feasibility with engineers, although this is not a data scientist role.
Solid grasp of 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; LLMs, APIs, SaaS AI services, and third-party ML products.
Strong understanding of agentic AI concepts (tool use, planning, orchestration).
Deep empathy for users — you think in flows, friction points, and moments of delight.
Hands-on involvement in user research; ability to put yourself in the shoes of customers.
Able to make decisions when surrounded by uncertainty and maintain momentum without a support system.
Able to lead by influencing without authority, aligning cross-functional teams around clear goals and driving outcomes through trust, clarity, and data-informed decisions.