Season 3 Episode 135: From the Navy to the NFL with Chris Bailey


After serving as a commanding officer, aviator and leader at the US Naval Academy, Chris Bailey retired from the US Navy. Even with the added challenge of the COVID-19 pandemic, Chris was able to utilize several transition programs that helped him to articulate what he wanted for his next career. When a role opened up with the Washington Commanders NFL team to lead their SALUTE veteran and military outreach and engagement program, it was like a dream come true. Chris speaks on his difficult transition as well as working in the professional sports industry.


In hindsight, Chris realized he coasted into retirement. Even with all the advice to start early, he did not listen. Chris had always dreamed of working in the sports industry, although during his transition he was not able to articulate what that might look like or how to make his dream a reality. Chris and his family had made the decision to stay in the Baltimore/DC area, so when the right opportunities weren’t coming up, he settled on looking for roles as a project manager or business development manager.


His first role in the private sector came after weeks of surfing job boards and LinkedIn job postings. Looking back, Chris realized he didn’t network, take the time to conduct informational interviews or find a real focus. Luckily, he fell into a role that a family friend offered. Chris admits that while he did take advantage of TAP, The COMMIT Foundation and FourBlock, he just went through the motions without putting in the real work of finding his focus and articulating his values.


After a year of working for his friend, Chris was ready to put in the hard work of networking and finding a role that better suited him. Chris conducted informational interviews and grew his network. Through his connections, he learned about a role that was a perfect intersection of his passion for sports and his passion for the military. Leading their SALUTE program, Chris’ job encompasses anything military related that touches the Washington Commander’s team. If you are interested in pursuing a job in the sports industry, most NFL teams participate in the SkillBridge program, including the Commanders.


Chris reflects on the perks of working for a professional sports team. His office overlooks the field, and his meetings often include giants in the football industry. Recognizing that he works with an outstanding community relations team, Chris does struggle with being an individual contributor in his current role. He misses the opportunity to provide leadership. As an officer in the Navy for 25 years, Chris was used to leading and mentoring teams while developing culture.


Chris advises transitioning service members to understand their financial situation. If you are retiring or receiving disability, calculate the numbers and know what level of compensation you require in your next career for your standard of living. Start preparing for your transition at least 1 year prior. Conduct informational interviews, find your focus, research companies and their culture and be able to articulate the value that you will bring to an organization. 


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