🏆 Career Insights: A Career in NFL Operations

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A Journey Through the NFL

Simon's path into football operations began as a student manager at Morgan State University. “What really excited me about working in football is that it’s not about one person; it’s about a team and everybody working together toward a common goal,” he reflects. This role gave him insight into the multifaceted nature of football, igniting his passion for a career in sports. However, breaking into the NFL wasn’t easy. Despite sending dozens of resumes to teams without success, his persistence eventually paid off when he landed a summer internship with the San Francisco 49ers as an equipment intern during his senior year.

Following this opportunity, Simon joined the Chicago Bears as a seasonal intern in the equipment room and later interned with D.C. United in Team Administration. He then transitioned to the Baltimore Ravens for another internship before securing his first full-time role with the Cleveland Browns. Simon spent nearly a decade with the Browns, beginning as an Operations Coordinator and rising to Director of Football Operations. After his tenure in Cleveland, he returned to the Chicago Bears as Director of Team Logistics & Business Process Liaison, where he spent three years. Simon ultimately came full circle when he joined the Ravens as Vice President of Operations, the role he held before being promoted to Senior Vice President.

Essential Traits & Going the Extra Mile

Having worked alongside some of the NFL’s best, Simon highlights three essential traits for success: building “relationship equity,” adaptability, and teachability. Unlike surface-level networking, Simon describes relationship equity as cultivating meaningful, reciprocal connections that open doors to opportunities. He underscores the importance of lifelong learning and maintaining a teachable mindset to thrive in the ever-evolving landscape of football operations. Adaptability, he notes, is critical in a field where unpredictable challenges – such as weather delays or logistical hurdles – are common. This ability to pivot and problem-solve quickly is often what separates exceptional professionals from the rest.

When building his team, Simon prioritizes individuals who go above and beyond, challenge the status quo, and leave things better than they found them. He values cultural fit as much as skill, seeking candidates who foster collaboration in an industry where colleagues often spend more time together than with their own families.

Celebrating the Wins & Staying Grounded

Simon’s advice to his younger self would be to enjoy the journey rather than obsess over the destination. Early in his career, he admits he was fixated on climbing the ladder. Over time, he’s learned to savor the relationships and experiences that define a fulfilling career. “Concentrate on the journey, on building relationships, meeting new people, and enjoying the ride. It's not always about reaching the destination—it's about finding fulfillment along the way."

For the past 15 years, Simon has kept a nightly routine that helps him stay grounded. He writes down 5-10 daily highlights in a notebook alongside to-do lists and follow-ups. At the end of the year, he revisits these moments, reflecting on both small and big victories. “Sometimes we focus so much on what went wrong that we forget to celebrate the wins,” he notes. “The wins build confidence and remind us of the progress we’re making.” This practice allows him to maintain gratitude and appreciate progress throughout the year.

His Why

For Simon, family is at the heart of everything he does. As a father to two daughters, he strives to show them that with hard work and dedication, they can achieve anything. “I want them to know they can be whatever they want to be,” he shares. His goal is to be a father they’re proud of, modeling hard work, consistency, and commitment.

This passion for helping others extends to his professional life, where Simon takes pride in mentoring interns, assistants, and staff. He sees himself as a champion for his team, working to make their journeys smoother than his own. Balancing a high-pressure career with fatherhood isn’t without its challenges, but Simon approaches both roles with purpose and presence, always guided by his “why”: leading by example.

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