Director of Data Science at CourtReserve – St. Augustine, Florida

CourtReserve is the market-leading platform for racquet sports club management, serving 2,000+ clubs and 5M+ players. Backed by MainSail Partners, we are building CourtReserve AI™, an intelligence layer that transforms platform data into actionable insight and product intelligence.

You will define how data is structured, analyzed, and leveraged across the company, while building the intelligence behind our AI product.

You will begin as a highly hands-on individual contributor, owning everything from raw data to deployed models, with a path to building and leading the data science function as the platform scales.

• Design and ship models that power intelligence around engagement, utilization, recommendations, and revenue optimization.
• Build systems that learn from real-world outcomes and continuously improve.
• Partner closely with Product and Engineering to embed intelligence directly into the user experience.

• Structure and unify data across product, payments, and customer behavior into a coherent analytical foundation.
• Analyze platform-wide trends across thousands of clubs to uncover key drivers of retention, revenue, engagement, and growth.
• Translate data into clear, actionable insights for leadership and cross-functional teams.
• Develop predictive signals that inform Customer Success, Sales, and strategic decisions.

• Help shape the modern data stack (Snowflake, dbt, event instrumentation, and similar tools)
• Define canonical data models used across both ML and analytical workflows.
• Ensure data is accurate, reliable, and structured for rapid iteration.
• Identify and close gaps in data collection and instrumentation.

• Own the full lifecycle from data exploration to modeling to deployment.
• Work directly with large, real-world datasets using SQL and a modern analytical programming language such as Python, R, or similar.
• Ship quickly, iterate based on usage, and improve over time.
• Leverage modern tools, including AI-assisted workflows, to accelerate development without compromising quality.
• Make practical decisions that enable fast progress, even when data, systems, and requirements are still evolving.

• Booking and utilization data across 2,000+ clubs
• Member lifecycle data for 5M+ players
• Payment and revenue data across multiple markets
• Program, event, and engagement data
• Cross-sport behavioral patterns
• Internal business data

You will be the first person to fully leverage this dataset.

• Experience building and shipping data science or ML systems used in real-world products.
• Strong foundation in working with behavioral or transactional data.
• Strong ability to work directly with data using SQL and a modern analytical programming language such as Python, R, or similar.
• Experience turning data into both predictive models and actionable business insights.
• Comfortable working directly with large, raw datasets and modern data platforms such as Snowflake, dbt, or similar tools.
• Ability to communicate complex ideas clearly to non-technical stakeholders.
• Comfortable operating independently and owning decisions end-to-end.

• Experience in SaaS, marketplaces, or multi-tenant platforms.
• Experience with recommendation systems, forecasting, or behavioral modeling.
• Experience partnering with Product, Customer Success, or Sales using data.
• Experience with modern data tools and AI-assisted development workflows.

• A research-focused role detached from product and business impact.
• A role focused primarily on dashboards or reporting layers.
• A role with a large team from day one.