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.

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!