AI Product Director

About Outdoorsy Group

Outdoorsy Group is the leading outdoor travel and digital insurance platform, powering road trips, adventure stays, and innovative insurance solutions in the specialty lines markets. With a profitable business, $3B in gross transactions, and a vision to reach $8B by 2029, we are building the future of outdoor travel. As we continue to scale, we are investing in AI to enhance our marketplace, operations, and customer experiences.

About the Role

We are looking for an AI Product Director to lead AI-driven product initiatives across Outdoorsy and Roamly. This role will be responsible for identifying, developing, and launching AI-powered features that improve efficiency, drive engagement, and create new revenue opportunities. You will work cross-functionally with engineering, data science, design, and business teams to define and execute our AI roadmap.

Key Responsibilities:

• Develop and own the AI product strategy, roadmap, and execution plan for AI-driven features and automation.
• Identify high-impact AI opportunities across Outdoorsy’s marketplace, customer experience, and Roamly’s insurtech offerings.
• Work with engineering and data science teams to develop and launch machine learning models and AI-powered solutions.
• Define success metrics, run A/B tests, and iterate based on data-driven insights.
• Collaborate with stakeholders (marketing, ops, legal, etc.) to align AI initiatives with business goals and customer needs.
• Stay up to date with AI trends, technologies, and regulatory considerations to ensure best practices.

What You Bring:

• 5+ years of product management experience, with at least 2 years in AI/ML-driven products.
• Strong understanding of AI/ML concepts, LLMs, and data-driven decision-making.
• Experience working with engineers and data scientists to build AI-powered products.
• Ability to define and analyze key performance metrics and iterate based on insights.
• Excellent communication and stakeholder management skills.
• Experience in marketplaces, travel, fintech, or insurance is a plus.

Why Outdoorsy?

• Opportunity to shape AI innovation in a fast-growing, profitable company.
• Work on cutting-edge AI applications in marketplaces, mobility, and digital insurance products.
• Collaborate with a passionate team in a high-impact role.
• Competitive salary, equity, and benefits.

Join us and help define the future of AI at Outdoorsy!

Benefits & Perks:

• Opportunity to contribute to a high-growth, mission-driven company.
• Competitive salary and equity in one of the world’s fastest-growing companies.
• Comprehensive health and welfare benefits.
• 401(k) match to help secure your future.
• Flexible PTO to promote work-life balance.

Salary: $180,000 - $200,000/yr DOE