Product Manager (AI)

Position Overview: Indagare is seeking an experienced Product Manager to lead the development of the Indagare AI — a proprietary engine model built on top of our decades of curated travel expertise, member insights, and global network of partners. The ideal candidate will own the vision, roadmap, and performance of the engine and the AI-powered experiences it enables, from internal tools for our Travel Desk and Trip Designers to member-facing trip planning. This role requires a strategic thinker with deep technical fluency in LLMs, strong product judgment, and the ability to work cross-functionally across engineering, data, content, and trip designer teams.

This is a fully remote, U.S. based position with an annual salary of $120,000.00. You will report to a VP of Product.

What You'll Do:

• Define and communicate the product vision, strategy, and roadmap for the Indagare AI in alignment with company goals and the evolving AI landscape.
• Translate member and trip designer needs into AI use cases, product requirements, and prioritized features.
• Partner with engineering, data, and external development partners on model selection, fine-tuning, retrieval (RAG), and agentic workflows.
• Own the data strategy behind the model — working with content, CRM, and analytics teams to curate, structure, and govern high-quality training and retrieval datasets.
• Establish evaluation frameworks to measure model quality, including accuracy, relevance, tone, personalization, and hallucination rates.
• Oversee the full AI product lifecycle, from prototyping and testing to launch, monitoring, and continuous improvement.
• Ensure the model reflects Indagare’s voice, editorial standards, and trusted recommendations.
• Define and uphold guardrails for responsible AI, including privacy, data security, explainability, and member trust.
• Gather and analyze user feedback to continuously improve model outputs and user experience.
• Communicate regularly with internal and external stakeholders on product status, milestones, and performance metrics.
• Define and track KPIs that measure both model performance and business impact.

What You'll Bring:

• 5+ years of experience in product management, including 2+ years building AI/ML or LLM-powered products.
• Hands-on understanding of LLMs, prompt engineering, RAG, fine-tuning, embeddings, and AI evaluation methods.
• Experience working with data pipelines and structured and unstructured datasets
• Proficient in data analysis (ideally SQL and Google Analytics) and able to make data-driven decisions.
• Strong understanding of software development processes. Ability to communicate technical and AI concepts to non-technical stakeholders.
• Familiarity with responsible AI practices, including privacy, bias mitigation, and model safety.
• Excellent verbal and written communication skills. Ability to present complex information clearly and concisely.
• Proven ability to lead cross-functional teams and manage external vendors or development partners.
• Travel, hospitality, or luxury industry experience is preferred.
• Experience working in a lean, dynamic startup culture is preferred.

About You:

• Self-starter who takes initiative and works challenges through to viable conclusions
• Curious and hands-on with emerging AI tools — you build, test, and learn quickly
• Collaborates with others to ensure better outcomes and build strong networks
• Problem solver with attention to detail and a high bar for quality
• Excellent communicator with a strong product point of view
• Based in Boston or NYC metro areas (preferable)