CHASING DREAMS

How to Land a Job in Sports

By: Trey Rose

Practical advice, real stories, and actionable strategies from inside professional sport front offices (MLB, NFL, NBA, NHL)

Introduction - Trey Rose

Trey Rose is a Baseball Operations executive with the Pittsburgh Pirates and the author of Chasing Dreams: How to Land a Job in Sports. Over the past decade, he has worked across roster management, player acquisition strategy, budgeting, player valuation, and organizational planning at the Major League level.A graduate of the Virginia Military Institute and the University of Florida MBA program, Trey is passionate about helping aspiring professionals break into the sports industry in a practical, authentic way. His mission is to provide honest guidance, actionable advice, and real-world insight into what it truly takes to build a career in sports.Through this website, Trey shares resources, lessons, and experiences designed to help others identify their passion, stand out from the crowd, and chase their dreams with purpose.

CAREER HIGHLIGHTS

Leadership and Impact

-Led hiring processes across 2,000+ interviews-Mentored interns now working in MLB and the NBA-Helped launch the organization’s first Culture Task Force-Built relationships across baseball operations and agents-Significant contribution in 2025–2026 offseason acquisitions-Published author of Chasing Dreams

WHY I WROTE CHASING DREAMS

Memories from the Game

-Driving our GM to Spring Training games as an intern-Sitting in Draft and Trade Deadline war rooms-Attending High School Graduation at Dominican Academy-Experiencing my first MLB Opening Day-Signing my first free agent, Wilmer Difo-Being part of the Konnor Griffin extension process-Trading for and signing my childhood best friend, Nathan Kirby

Why I Wrote Chasing Dreams

Breaking into the sports industry can feel overwhelming, competitive, and incredibly difficult to navigate. For many people, there is no clear roadmap, no playbook, and very little transparency around what it truly takes to build a career in professional sports. Throughout my own journey in Major League Baseball, I realized that many aspiring professionals were not lacking passion or work ethic; they simply needed honest guidance, practical advice, and real insight from someone who had experienced the process firsthand.I wrote Chasing Dreams to help pull back the curtain on the sports industry and provide the type of resource I wish I had when I was starting my career. The book combines lessons from my own journey, stories from inside baseball, and actionable strategies designed to help others stand out, build meaningful relationships, and pursue opportunities with purpose and confidence.More than anything, I hope this book encourages people to chase ambitious goals without losing sight of who they are in the process. While the path into sports is rarely easy, I believe the journey can be incredibly meaningful when approached with humility, persistence, curiosity, and genuine care for others.

WHAT YOU WILL LEARN IN CHASING DREAMS

What You Will Learn in Chasing Dreams

WHO THIS BOOK IS FOR-College students looking to break into sports
-Former athletes searching for their next chapter
-Career switchers pursuing a new passion
-Young professionals trying to grow within the industry
-Anyone chasing a career in sports
WHAT YOU WILL LEARN-How to stand out in the sports industry
-Networking and relationship-building strategies
-Résumé, questionnaire, and interview advice
-How to gain meaningful experience and skill sets
-Lessons from inside professional sports from interviews with executives, coaches, scouts, analysts, agents, and more
-The realities of working in sports
-Leadership and career growth principles
-How to handle rejection and setbacks
-Ways to separate yourself from the competition

BACK TO THE HOME PAGE

PURCHASE
BOOK

A practical and honest guide to breaking into the sports industry, building relationships, and turning passion into a career.

PURCHASE WORKBOOK

An interactive companion filled with reflection prompts, exercises, and actionable tools to help you apply the lessons from the book.

PREMIUM RESOURCES ($10)

Includes the following:
-All Free Resources
-Interview guide
-Questionnaire and Case Guide
-Advanced Networking and Application Tracker
-Side Project Ideas
-Skill Set Guide

FREE CAREER RESOURCES

Includes the following:
-Resume Guide
-Informational Interview Guide
-Lite Networking Tracker

Contact Us

Thank you for visiting the site and for your interest in Chasing Dreams.Due to the demands of working in professional sports, I may not be able to respond to every message individually. This page is primarily intended for speaking engagements, podcast appearances, media opportunities, and book-related collaborations.If your inquiry aligns with one of those areas, please fill out the form below. I appreciate the support and look forward to connecting.

Thank You

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