Dylan Gilbert: What It Takes to Go from Campus Manager to Associate Director
Picture this: you're a student from the University of Michigan, scrolling through college scholarship applications, just trying to make ends meet. That was Dylan Gilbert. He had no idea applying to a scholarship he found online would lead to a career-changing opportunity with Fresh Prints. Fast forward a few years, and he’s now the Associate Director of Inside Sales—proof that undergraduate job opportunities can turn into long-term careers.
Dylan’s story is all about taking chances, stepping out of his comfort zone, and finding the right people to push him forward.
Becoming a Campus Manager at Fresh Prints
At first, Dylan assumed sales would be easy. He sent messages, got positive replies, and expected success to follow. Spoiler: it didn’t. The breakthrough came when he took full ownership.
He managed to bag $27,000 in sales in his first semester. Then winter break hit, and his motivation completely disappeared (real). When he returned to campus, his sales struggled, and the excuses started piling up. By spring 2019, he was this close to quitting.
That all changed when Dylan met Sofie Rosofsky, his new manager. Under her mentorship, Dylan ditched the excuses and started treating his business like, well, a business. That semester he pulled in $80,000 in sales! The experience gave him the workplace skills he never knew he needed—time management, negotiation, and leadership—all of which would later help him land a fresh graduate job with Fresh Prints.
As a history major, Dylan had zero sales experience. But he quickly found that success comes when you step outside your comfort zone. "College makes it easy to stay comfortable—take easier classes, get better grades. But real growth happens when you push yourself," he says. Many job opportunities for university students were just a way to make extra cash, but being a Campus Manager at Fresh Prints had the potential to be a real stepping stone.
Transitioning into the BDM Role at Fresh Prints
Fresh Prints surprised Dylan when they offered him the BDM role—an opportunity that, until then, only Sofie had taken on full-time after her CM days. It was a huge step forward and showed him that real-world experience could be just as valuable as a degree when figuring out how to get a job after college. They flew him to NYC for a weekend to meet key players like Jacob (Director of Sales), Josh (CEO), and Jolijt (VP of Growth). "I had the most amazing weekend. I knew Fresh Prints was where I wanted to be," he recalls.
What really got him excited was the challenge of managing a team with completely different approaches to closing deals. Working with such a diverse team forced him to adapt his own leadership style and embrace sales strategies he’d never considered before. That’s when he truly realized the value of specialized skills and training in becoming an effective leader.
Every day was a steep learning curve, and he often felt in over his head. But the chance to influence outcomes on a $4 million scale—far beyond the $150,000 sales he made as a CM—seriously lit a fire in him. "It's not about the industry; it's about the role and how much you can grow into it," he said.
Becoming the Associate Director of Inside Sales at Fresh Prints
Stepping into the Associate Director of Inside Sales role has become Dylan's new obsession. Now, he's crafting the long-term vision for inside sales, making decisions with years in mind rather than just chasing daily numbers, all to drive serious growth year-over-year.
“Seven years ago, I had no idea how sales worked, five years ago I had no clue how to manage people, and a year ago, directing managers was completely new to me,” Dylan admitted. Throughout the past five years, he's picked up tons of valuable insights (especially from feedback sessions with Jacob) that have shaped his approach and helped him support other managers as they build their teams. Staying disciplined and sticking to solid habits means he squeezes the most out of every week.
When asked what excites him most about leading inside sales, Dylan doesn't hesitate: "I'm all about building something bigger and watching everyone I manage grow into roles that may not even exist yet." The inside sales team is already an $11 million operation, but Dylan is excited to expand beyond collegiate accounts into corporate and other markets in a billion-dollar industry.
Dylan sees work and life as one connected journey, and even though he's incredibly driven, he still makes time for fun along the way. Despite starting with zero knowledge of sales or management, Fresh Prints' supportive, fast-paced environment gave him the perfect runway to grow into the role he crushes today.
Pushing inside sales to $20 million is Dylan’s focus this year, but he’s just as fired up about the Bills' Super Bowl chances.
Dylan’s Advice for Aspiring Campus Managers
For anyone hoping to move up from being a CM, Dylan's advice is straightforward: You're in control of your future. "No one else decides where you go—only you do," he says. "Even though you might feel overwhelmed sometimes, remember that no decision is set in stone. If you love it here and feel like you're growing, just give it your all. One day, you'll look back and be proud of what you've built."
Inspired by Dylan's journey? This could be your story too. If want to build real-world skills while still on campus, the Campus Manager role at Fresh Prints might be your perfect launchpad. With the right mindset and steady, disciplined habits, you could be the next success story. Schedule a call with us to get started.
P.S. There are plenty of paths you can take with your CM experience. Check out how Carson went from Campus Manager to Entrepreneur, Lexi to an EY Consultant, and Valerie to an Assistant Merchandise Planner at Abercrombie & Fitch!