Great Leader in the Spotlight: Jackson Montgomery

Jackson Montgomery is an outstanding leader you need to know. He serves as the Director of Commercial at Think Big, which has helped brands and companies like NASCAR, DoorDash, and the Milwaukee Bucks solve their toughest advertising challenges and unlock incredible growth through an extraordinary blend of creative strategy and data insights. It has been my privilege to meet with and learn from Jackson, and he graciously shared the following perspectives: 

1. Why do you love what you do?

“I love what I do because it’s constantly evolving. Meeting new people, discovering opportunities, and negotiating deals—it’s like riding the crest of a wave that never stops. The challenge is to stay in motion, adapt, and ride that wave. The excitement comes from the unpredictability; no two days are the same, and each new connection or insight adds a fresh layer of complexity and possibility to the journey. It’s that continuous momentum and growth that keeps me energized and passionate.” 

2. What makes your mission unique?

“My mission stands out because of our unparalleled focus on data. We harness the power of data to craft marketing strategies, and every time we dive into a client’s data, we uncover a new narrative. The constant evolution of tools, like AI, pushes us to refine and enhance our offerings. For us, staying ahead of these technological shifts is more than just keeping up with trends—it’s about mastering them to deliver clear, cutting-edge solutions. Each client’s story is different, and our mission is to uncover that story and use it to strengthen their strategy.” 

3. Who is the leader who has inspired you the most and why?

“There are too many impactful leaders in my life that it’s impossible to name just one. What stands out to me is a common thread among them: they’ve always had my best interests at heart, consistently pushing me to step outside my comfort zone. The leaders who inspire me the most are the ones who take the time to explain why. When someone can break down the reasoning behind their guidance, it doesn’t just help you grow—it builds trust, clarity, and respect. That ability to clearly articulate the "why" behind every decision is what I strive to emulate in my own leadership style.” 

It is my distinct honor and privilege to know Jackson Montgomery . His exemplary reflections and learning shared have taught so many, myself included that the right marketing strategy isn’t about following trends. It’s about building mutual respect, lasting value, and trust for those whom we serve, supported through data-driven creativity, inspiring messages that resonate, and scalable systems that deliver lasting excellence. His sterling character, integrity and commitment to service have made him a great leader among leaders in developing the next generation to exceed expectations with honor. Keep charging, Jackson!