Robert “Fitz” Gentry: Journey of Naval Flight Officer to 2 Circle
Robert “Fitz” Gentry: Journey of Naval Flight Officer to 2 Circle
From flying missions as a Naval Flight Officer (NFO) to leading at 2 Circle, Fitz’s journey is defined by leadership and passion.
Above all, he stays true to the values his father taught him: love of country, service before self, and working for others.
Robert “Fitz” Gentry was shaped by his childhood heroes.
One of them was Roger Staubach: Navy quarterback, Heisman Trophy winner, Vietnam Supply Corps Officer, and NFL legend. Staubach’s story lit a fire in young Fitz, showing him the heights one could reach with dedication and courage.
Fitz also found inspiration closer to home in Williamsburg, Virginia. At the marina just outside of Williamsburg, where his dad kept a sailboat, he met a neighboring sailor who was an airline pilot and former Vietnam F4 pilot. The pilot’s thrilling stories of flying and service captivated Fitz, fueling his fascination with aviation.
But the most profound influence was his father. After losing his mother at age two, Fitz was raised by his dad, who left a college coaching job to coach high school, just to be there for his son.
“Watching him help young kids achieve their dreams or find purpose made a huge impact on my life,” Fitz says. His father’s lessons in “love of country, service before self, and working for others” became Fitz’s core values.
All three influences combined to ignite his passion for service and naval aviation. “I wanted to be a naval aviator,” Fitz says. “And I wanted to fly jets on carriers.”
Naval Flight Officer Journey
Fitz started his journey at the U.S. Naval Academy, where he graduated with a B.S. in History. Shortly after, in 1996, he earned his wings and became a Naval Flight Officer (NFO). In September of that year, he joined VAQ-129 “Vikings” as an EA-6B Prowler student naval aviator, later moving to VAQ-138, the “Yellow Jackets,” for a WESTPAC cruise.
In 1999, Fitz found himself at Aviano Air Base in Italy, part of Operation Allied Force over the Balkans. This was a game-changer. His Commanding Officer, Todd “Zeke” Zecchin, pushed Fitz and three others to take charge of the mission. “That experience, and the chance to step up during Allied Force, kept me in the Navy,” Fitz says.
Fitz transitioned to flying F-14 Tomcats in September 2000, joining VF-101, the “Grim Reapers,” and then VF-143, the “Pukin Dogs,” where he completed two more cruises. He served as Assistant Department Head and later Department Head with VF-31, the “Tomcatters.”
A career highlight came on October 4, 2006. Fitz flew the last U.S. Navy Tomcat, “Felix 101,” from NAS Oceana to Republic Airport in Farmingdale, New York.
Thousands of Grumman employees, who had worked on Tomcat products for generations, greeted him with hugs and tears. “I couldn’t have written that into a career… but experiencing it was priceless,” Fitz shares.
Following this unforgettable experience, Fitz served as a Strike Fighter Placement Officer from 2006 to 2008. He oversaw policy and assignments for numerous aviation squadrons, carrier air wings, weapons schools, and the Blue Angels.
He then pursued further education at the Australian Command and Staff College, focusing on strategy, operations, and organizational effectiveness. Upon returning from Australia in late 2009, Fitz screened for Squadron Command and transitioned to his third platform, the F/A-18 Super Hornet.
As XO and CO of VFA-103, the “Jolly Rogers,” he led his squadron through back-to-back deployments from January 2010 through July 2013.
Reflecting on this time, Fitz says, “To have the opportunity to command a squadron with authority and all the responsibility that comes with it was a truly humbling experience. And to be slated to a squadron whose heritage goes back to World War II and has deep traditions meant a lot.”
There’s no better job than O5 squadron command because it is your people, squadron, and aircraft.
Robert “Fitz” Gentry
Then, in December 2014, he went on to become Chief of Staff for the Commander of Naval Air Forces Atlantic, Admiral Mike Shoemaker, who became the 7th “Air Boss” in January 2015. ADM Shoemaker encouraged him to take a job with the Joint Chiefs of Staff. There, Fitz supported USEUCOM and their joint training exercises.
In January 2017, Fitz screened for Major Command and took the helm of Carrier Air Wing One in Oceana, with 73 aircraft and eight fleet squadrons under his leadership until August 2020.
But for Fitz, the true highlight was having the opportunity to lead, guide, and mentor his team.
Transitioning to O6 Command, Fitz found even greater fulfillment in mentoring squadron COs and impacting the lives of young sailors. “Walking onto the flight deck or anywhere else to talk to a young kid missing home or having a rough day was incredibly rewarding,” Fitz shares.
“Spending those few minutes to explain their contribution to training or combat missions, investing in them and getting their buy-in, made a real difference to mission success. Helping them get to career school, writing letters of recommendation for commissions or their next milestone — that was the best part.”
From the Cockpit to Civilian Life
After his stint as Commander of Carrier Air Wing One, Fitz took on the role of Executive Director of Special Projects at Naval Air Force Atlantic in 2020.
He joined 2 Circle in May 2021 and found a role that allowed him to continue serving the warfighter while being more present for his family. “I had several friends who were working for 2 Circle. Everyone I spoke with had the same story. Great company. Great people. Great mission. A company with values that mirror those that matter while you’re wearing a uniform, with a strong focus on family and better balance across your life.” he recalls.
Another key consideration for Fitz when seeking a career was finding a company that would support his professional and academic goals. 2 Circle provided this support, allowing him to pursue an MBA, which he completed in May of 2023.
“I figured out what I wanted to do in phase two of my life… I had already applied to and got accepted to Notre Dame. So, I needed something that would support pursuing that opportunity,” he explains.
Fitz used 2 Circle’s Educational Assistance Program, which contributes up to $5,000 a year to support employees’ career and educational goals. “The support from 2 Circle made balancing work, family, and education manageable,” he says.
“That communal success of watching the company grow and affording people opportunities aligns extremely well with the values I hold dear,” Fitz says. “When you can be a part of a company that cares, even in small ways, it cements your commitment.”
At 2 Circle, Fitz supports NAVAIR’s Strike Planning and Execution Systems, known as PMA-281, by helping with the development of cutting-edge mission planning software for naval aviation. “We’re working on a next-generation mission planning system, now called Collaborative Mission Planning Continuum (CMPC),” Fitz explains.
This involves crafting software that seamlessly integrates program management and operational expertise, ensuring that the needs of fleet operators align with the engineering efforts at PMA-281. “Our goal is to ensure the capabilities we’re developing meet warfighter requirements,” he says.
Beyond this, Fitz also supports the Office of the Secretary of Defense in tackling the American mid-band initiative and sell-off of spectrum. He focuses on its impact on military training, especially electronic warfare training. “We’re developing capabilities to train for high-end fights, even as the spectrum gets sold off,” Fitz elaborates.
Over the past year, Fitz has expanded his responsibilities at 2 Circle by taking on multiple roles, including Director of Business Development and CEO Advisor. These positions allow him to leverage his extensive military experience and leadership skills in innovative ways.
“[The CEO Advisor] role is a wide-ranging, evolving position that supports the CEO and all of his functions and roles,” he explains. In business development, Fitz’s mission is to help the company grow strategically while maintaining its core values. “We want to ensure that 2 Circle grows with a purpose. It must be meaningful and align with our core competencies and mission statement,” he says.
The Road Ahead
Looking to the future, Fitz has big aspirations. First, and most importantly, is to be a great husband and father.
Second, is to continue evolving in more challenging roles at 2 Circle, leveraging his academic and naval aviation skillset to be a great leader. He envisions a future where he steps into a C-suite role or runs his own company.
Fitz says. “I’m ambitious, driven to achieve things and to continue growing personally and professionally,” Fitz says. “When I retired, I knew I had a lot of gas left in the tank. And I still do.”
The Road Ahead
Looking to the future, Fitz has big aspirations. First, and most importantly, is to be a great husband and father.
Second, is to continue evolving in more challenging roles at 2 Circle, leveraging his academic and naval aviation skillset to be a great leader. He envisions a future where he steps into a C-suite role or runs his own company.
Fitz says. “I’m ambitious, driven to achieve things and to continue growing personally and professionally,” Fitz says. “When I retired, I knew I had a lot of gas left in the tank. And I still do.”