Amateur Scouting Assistant

JOB TITLE: Amateur Scouting Assistant 

DEPARTMENT: Amateur Scouting 

ORGANIZATION: Chicago Cubs 

REPORTS TO: VP, Amateur Scouting & Director, Amateur Scouting Operations 

LOCATION: Chicago, IL  

FLSA STATUS: Exempt

COMPENSATION:   $60,000 - $70,000 USD 

BEING PART OF THE TEAM 

Our business is a team sport that began on a field with baseballs and bats and has evolved into one of the most recognizable brands in sports and entertainment through Cubs baseball and live events. Our success is driven by our people, who work to create and inspire change in an engaging, collaborative and inclusive environment. As a team, we continue to build a culture on and off the field that delivers unforgettable experiences for one another, our fans and community. In support of that effort, we expect associates to work primarily in our office. Are you ready to be part of it? 

OUR STORY 

THE CHICAGO CUBS FRANCHISE, a charter member of Major League Baseball’s National League since 1876, has won the National League pennant 17 times and was the first team to win back-to-back World Series titles in the 1907 and 1908 seasons. In 2016, the Chicago Cubs made history again when the team won its first World Series in 108 years, ending the longest championship drought in North American sports. Known for its ivy-covered outfield walls, hand-operated scoreboard and famous Marquee, iconic Wrigley Field has been the home of the Chicago Cubs since 1916 and is the second oldest ballpark in Major League Baseball. In 2009, the Ricketts family assumed ownership of the Chicago Cubs and established three main goals for the organization: Win the World Series, Preserve and Improve Wrigley Field, and Be a Good Neighbor.  

HOW YOU’LL CONTRIBUTE 

The Amateur Scouting Assistant will support the department’s day-to-day operations and core scouting workstreams, including prospect data management, general draft preparation, pre-draft workouts, and special projects. This role will help ensure that information across scouting systems is accurate, complete, and timely while coordinating departmental processes and supporting Amateur Scouting leadership throughout the player evaluation and draft cycle. Through careful data stewardship, consistent process execution, and responsive support, the assistant will help create a strong operational foundation for informed player evaluation and draft decision-making. 

This position offers broad exposure to the Amateur Scouting landscape and opportunities to collaborate with departments including Scouting, Research & Development, Medical, and Player Development. The ideal candidate will demonstrate strong organizational and interpersonal skills, exceptional attention to detail, and the ability to manage multiple priorities in a fast-paced environment. Prior baseball experience is not required; however, a strong passion for the game and an interest in player evaluation are essential. This role will be based full-time in Chicago, IL. Travel will be extensive during primary scouting months. 

THE DAY-TO-DAY: 

• General Draft Preparation: Support year-round draft preparation by maintaining prospect information and organizing data from various sources. Help prepare draft-related reports, lists, and reference materials and ensure required information is finalized before departmental deadlines. 

• Amateur Data Management and Audit: Maintain accurate and complete amateur player records across departmental systems. Perform routine data entry, cleaning, deduplication, player-profile maintenance, pitch classification, data merges, and quality-control audits. Monitor data pipelines and logs, identify discrepancies, and coordinate with appropriate partners to resolve issues before key deadlines. 

• Pre-Draft Workout Support: Assist with the planning and execution of amateur player workouts, including participant tracking, scheduling support, preparation of player information, collection of measurements and performance data, and post-workout data entry. Review workout information for accuracy and completeness and ensure results are distributed to relevant stakeholders in a timely manner. 

• Player Evaluation Support: Provide supplemental scouting support at amateur events as assigned, including tournaments, showcases, workouts, and regular-season games. Assist with the collection and organization of video, statistical information, and other player-evaluation materials. 

• Cross-Functional Collaboration: Identify opportunities to improve the accuracy, efficiency, and consistency of scouting workflows. Document recurring processes and collaborate with Scouting, Research & Development, and other departments on data-quality, reporting, and special-project needs. 

• Additional Departmental Support: Perform other duties (e.g. departmental administration / logistical oversight) and special projects as assigned, adapting to shifting priorities and increased workload during workouts, the primary scouting season, and the period leading up to the draft. 

WHAT YOU’LL BRING: 

• Bachelor’s degree in a quantitative and analytical field (e.g. Statistics, Finance, Engineering, Computer Science, Applied Mathematics, Operations Research)  

• Candidate to possess skills and background to contribute to department’s analytical and modeling efforts, including but not limited to collaborating with VP and the R&D department 

• Exceptional organizational skills, attention to detail, and commitment to maintaining accurate and timely information 

• Strong analytical and problem-solving skills, with the ability to identify data discrepancies and coordinate their resolution 

• Ability to manage multiple projects, shifting priorities, and time-sensitive deadlines in a fast-paced environment 

• Effective written and verbal communication skills, including the ability to present information clearly and concisely 

• Proficiency with standard workplace productivity tools and the ability to learn new databases, scouting systems, and technologies. 

• Strong passion for baseball and demonstrated interest in amateur scouting and player evaluation; prior professional baseball experience is not required 

WHAT SETS YOU APART:  

• 2+ years of experience with data analysis and management, operational support, project coordination, or related functions 

• Familiarity with baseball statistics, scouting terminology, or player evaluation concepts 

• Experience working with datasets, databases, or analytics tools 

• Exposure/Proficiency with SQL, Python, R, and AI tools  

TOTAL REWARDS:  

• On-site parking 

• Transit benefits 

• Paid time off: Personal, Sick, Vacation Time, Office Holidays & Winter Break  

• Flexible work arrangement  

• Casual work attire environment  

• Complimentary Meal & beverage plan 

• Cubs home game & spring training game ticket allotment  

• Access to campus wide Wrigley Field events & pre-sales 

• 401K Plan Employee Contribution & Employer Match   

• Benefit Plans: Medical, Dental, Vision & Life Insurance  

• Health & Wellness engagement & programming 

• Variety of associate special events, volunteer opportunities and partnership discounts 

• Monthly allotment for internal rewards & recognition platform  

• Tuition Reimbursement  

• Complimentary access to EV charging stations 

• Subscription to Marquee Sports Network