About Outdoorsy Group

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

About The Role

We are seeking Machine Learning Engineers and Data Scientists to develop and deploy AI models that drive automation, improve decision-making, and create seamless customer experiences. This role will play a critical part in shaping the AI foundation of Outdoorsy's marketplace and Roamly's digital insurance platform and product solutions.

Requirements

Key Responsibilities:

Design, develop, and deploy machine learning models to enhance search, pricing, fraud detection, personalization, and customer support automation
Build scalable data pipelines and infrastructure to support AI applications
Work with structured and unstructured data to develop predictive and generative AI models
Collaborate with product managers, engineers, and business teams to integrate AI solutions into production systems
Continuously optimize models for accuracy, speed, and efficiency
Stay current with the latest advancements in AI/ML and apply best practices to our business challenges

What You Bring:

5+ years of experience in machine learning, data science, or a related field
Proficiency in Python, TensorFlow, PyTorch, or other ML frameworks
Experience building, training, and deploying ML models at scale
Strong understanding of data engineering, feature engineering, and MLOps
Experience working with large datasets, cloud platforms (AWS, GCP, Azure), and databases
Familiarity with LLMs, recommendation systems, or predictive analytics is a plus

Why Outdoorsy?

Opportunity to apply AI/ML in a fast-growing, profitable marketplace and insurtech business
Work on cutting-edge AI challenges in travel, mobility, and insurance
Collaborate with a passionate team in a high-impact role
Competitive salary, equity, and benefits

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

Benefits

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: $165,000 - $185,000/yr DOE

Outdoorsy

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