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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

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Average salary estimate

$190000 / YEARLY (est.)
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$180000K
$200000K

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What You Should Know About AI Product Director, Outdoorsy

Are you ready to take your career to new heights? Join Outdoorsy Group as an AI Product Director and lead the charge in revolutionizing our AI-driven product initiatives! At Outdoorsy, we not only value adventure but also innovation, as we continuously strive to enhance outdoor travel experiences through cutting-edge technology. With a profitable business model and ambitious goals, your role in shaping our AI roadmap will be critical. You’ll have the opportunity to collaborate with talented engineers, data scientists, and designers across the company. Your expertise will help us develop AI-powered features that drive efficiency, boost customer engagement, and unlock new revenue streams. Whether diving into machine learning models or aligning AI strategies with business objectives, this role is all about impactful collaboration and creativity. Plus, you’ll get to stay ahead of the latest AI trends and best practices, creating an environment of growth and learning. If you have over 5 years of product management experience, including a solid background in AI/ML, we would love for you to bring your talents to our dynamic team. Competitive salary, equity options, and a supportive work culture await you at Outdoorsy. Let’s redefine the future of AI together!

Frequently Asked Questions (FAQs) for AI Product Director Role at Outdoorsy
What are the key responsibilities of the AI Product Director at Outdoorsy Group?

As the AI Product Director at Outdoorsy Group, you will be crucial in developing and executing the AI product strategy and roadmap. Key responsibilities include identifying high-impact AI opportunities, collaborating with engineering and data science teams to launch AI-powered solutions, defining success metrics, running A/B tests, and engaging with various stakeholders to align AI initiatives with business goals.

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What qualifications are needed for the AI Product Director position at Outdoorsy Group?

To succeed in the AI Product Director role at Outdoorsy Group, you should have over 5 years of product management experience, with at least 2 years focused on AI/ML-driven products. A strong understanding of AI and machine learning concepts, alongside excellent communication and stakeholder management skills, is essential. Experience in fields like marketplaces, travel, fintech, or insurance will also be beneficial.

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How does the AI Product Director role at Outdoorsy Group contribute to the company's future?

The AI Product Director role is pivotal in driving innovation at Outdoorsy Group. By leading AI initiatives, you will enhance customer experiences, streamline operations, and create new revenue opportunities, helping the company achieve its ambitious goal of reaching $8 billion in gross transactions by 2029.

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What benefits does Outdoorsy Group offer for the AI Product Director role?

Outdoorsy Group provides a competitive salary ranging from $180,000 to $200,000, equity in a fast-growing company, and comprehensive health and welfare benefits. Additionally, you will have a flexible PTO policy, a 401(k) match to enhance your financial security, and the opportunity to make a significant impact within a mission-driven organization.

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What is the work environment like for the AI Product Director at Outdoorsy Group?

Working as the AI Product Director at Outdoorsy Group means being part of a passionate and innovative team focused on transforming outdoor travel through technology. You will collaborate across teams, engage in meaningful projects, and enjoy a supportive culture that promotes work-life balance and professional growth.

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Common Interview Questions for AI Product Director
Can you describe your experience with AI/ML-driven products?

When answering this question, highlight specific projects where you played a key role in developing AI or machine learning-driven products. Discuss the challenges you faced, the methodologies you employed, and the impact your contributions had on the product's success.

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What is your approach to defining success metrics for AI products?

It’s important to articulate a systematic approach to defining success metrics. Discuss how you prioritize metrics that align with business objectives, incorporate user feedback, and use data analytics to continuously iterate on the product's performance.

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How do you collaborate with cross-functional teams?

Explain your strategies for effective collaboration, including regular communication, setting shared goals, and utilizing collaboration tools. Provide examples of how you’ve previously worked with engineering, data science, or marketing teams to achieve project goals.

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Describe a time when you identified a high-impact AI opportunity.

Share a relevant story where your insights led to the identification of a significant AI opportunity. Explain the problem you aimed to solve, the steps you took to investigate the opportunity, and the outcomes of your initiative.

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How do you stay updated with AI trends and technologies?

Discuss the resources, such as industry publications, conferences, webinars, or networks, that you follow to keep abreast of the latest AI trends. Highlight how you apply learnings from these resources to influence your work.

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What challenges are commonly faced when launching AI-powered features?

Identify typical challenges such as data quality issues, model deployment, user comprehension, and ethical considerations. Discuss how you mitigate these challenges and ensure the successful launch of AI features.

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How do you handle stakeholder management in AI projects?

Explain your proactive approach to stakeholder management, including regular updates, seeking feedback, and ensuring all parties are aligned with project goals. Provide examples of your successful strategies in managing stakeholders in past projects.

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What is your experience with A/B testing for AI products?

Discuss your understanding and practical experience with A/B testing. Provide examples of past A/B tests you have conducted for AI products, what you were testing, and how the results guided your product decisions.

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Can you provide an example of how you have driven user engagement in an AI product?

Share a specific case where your initiatives directly contributed to increased user engagement. Detail the strategies you used, such as personalization or enhanced user experience, and the measurable outcomes of your efforts.

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What do you envision as the future of AI in outdoor travel?

Articulate your vision for AI's role in transforming outdoor travel. Discuss potential innovations, customer benefits, and how companies like Outdoorsy can lead this evolution.

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Outdoorsy is the largest and safest community-driven marketplace platform that connects RV owners with other campers. They are committed to mobilizing the 56+ million underutilized, idle RVs around the world.

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Full-time, remote
DATE POSTED
February 20, 2025

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