Chatting with the Chief: Senior Enlisted Advisor Chief Master Sgt. Kevin Osby Prepares to Bid Farewell

As senior enlisted advisor, Chief Master Sgt. Kevin “KO” Osby is one of the most recognizable faces at the Exchange—and often is the face of the Exchange, working as a liaison between stores and commands and speaking with the media about Exchange events.

When he joined the Exchange in August 2020, though, it was hard to recognize anyone’s face—if he even saw a face in person.

“It was probably the weirdest way to check into an organization,” said Osby, who is retiring from the Air Force this summer and ending his tenure as the Exchange’s senior enlisted advisor. “I got here at the height of COVID, there was really nobody at headquarters besides the Airman here to check me in. We were in the building, but we sent all my stuff virtually to Sheppard Air Force Base and then they gave me a couple of Teams meetings to attend and told me that I had a podcast to host.”

Chief Master Sgt. Kevin Osby talks with celebrity chef Robert Irvine onstage at the 2023 Express Seminar. Osby, who was Exchange senior enlisted advisor from August 2020 to 2024, is retiring from the Air Force this summer.

Among the first people he met were Julie Mitchell (now Vice President, Marketing Customer Engagement) and Leah Miller (now Senior Marketing Manager), his first co-hosts on “Chief Chat,” a Facebook Live series that was started under the previous senior enlisted advisor, Chief Master Sgt. Luis Reyes. It was a while before he met anyone else in person.

“Everybody else was a picture on Teams,” Osby said. “It was interesting trying to put faces with names, because when you did finally meet people in person, they had a mask on. So you had to memorize foreheads. And then once people stopped wearing masks, I had to relearn people, because I hadn’t known what their actual faces looked like.”

Even back then, people recognized Osby, because he was in uniform. People would say “Hey, Chief,” and he would have to concentrate to remember where he knew them from.

“That’s just not a typical way that a military member comes into a unit,” Osby said. “But I love challenges and I wanted to jump in and figure out ways I could bring value to the Exchange. Let people know what I bring to the fight and how they could use me to better the organization.”

Opening up—and opening eyes

By 2021, COVID levels were down enough to allow Osby to travel. He conservatively estimates that he’s visited 60 to 70 installations and facilities as the Exchange’s senior enlisted advisor.

“When I first got here, I received talking points and I’d get questions,” Osby said. “At first, I didn’t have immediate answers. But I read Corporate Communication’s FAQs. I hadn’t realized how many different lines of effort were involved.”

Osby learned by doing as well as by reading. He visited the Exchange bakery and water plant in Gruenstadt, Germany to see how the Exchange provides baked goods and water for Quality-of-Life activities across Europe. He got a behind-the-scenes look at the school meal program that serves millions of meals yearly to children in Europe and the Pacific.

“Things like that opened my eyes, because as on the other side, as a customer, I’d looked at AAFES as your store where you buy your stuff with no tax,” Osby said. “When you go downrange, you appreciate it a little bit more, because someone is selling you goods and services in a combat zone. But visits like those made me see that the Exchange is more than just a retail store.”

He began to more deeply appreciate the flexibility of store managers who would go out of their way to bring requested products to their stores, as well as the passion of associates serving those who serve and have served.

“I saw it every time I went to a base or a post,” Osby said. “It made me smile to see how much the associates care about the military, either in garrison or on the front lines.”

In a 2021 photo, Exchange Senior Enlisted Advisor Chief Master Sgt. Kevin Osby presents a lapel pin to Lt. Col. Dennis Haessig, who served in Vietnam in 1972 and ’73, at the Commanders’ Classic game between the Air Force Falcons and Army Black Knights.

Time for ‘Chief Chat’

Osby proved to be an engaging host for “Chief Chat,” the Exchange’s 2020 to 2023 series that featured interviews with celebrities who were military supporters, as well as interviews with military officials themselves. But he had to get over some nerves at the beginning.

“It caught me completely off-guard at first,” Osby said. “I could always have a conversation with people, but doing a webcast where thousands of people could watch you interviewing somebody, I just never pictured myself doing that.”

Osby lists Dwayne “The Rock” Johnson and Garth Brooks among his favorite guests. For the Rock, he was able to bring on an Airman who was a big fan of the actor. When Brooks was a guest, Osby was visiting Cannon Air Force Base, where he asked wing leadership to help him find Airmen who were fans of the singer.

“I was able to get six or seven Airmen on the line with Garth Brooks,” Osby said, “and he went one by one and talked to each one of them and gave shout-outs to their parents. That was a cool moment, to be able to share the stage with those Airmen. It showed the wing how much we were there for them.”

(You can watch the Rock episode here and the Brooks episode here. All “Chief Chat” episode are available here on YouTube.)

While he was the interviewer on “Chief Chat,” Osby is often the interviewee when military or civilian media report on an Exchange event or initiative. He says working with Corporate Communication teammates helped prepare him for that role.

“Before I was the spokesperson for the Exchange, I was never an in-front-of-the-camera person,” Osby said. “And I’m still not, to be honest. It’s not the most comfortable thing for me but I’m able to flip the switch and turn it on. Once I turn it off, I’m usually saying, ‘Oh my God, that was nerve-racking.”

27 years of service

Osby’s military career began in September 1997, when he joined the Marine Corps in September 1997. He separated from the Marine Corps in 2001—four days before 9/11. In January 2002, he joined the Air Force Reserve in Barksdale Air Force Base, La., in the health service management career field and transitioned to Air Force active duty in 2005.

In October 2008, Osby deployed to Baghdad, Iraq, as an individual augmentee working in a joint environment as a Joint Operations Center Medical Liaison NCO. His awards and decorations include the Defense Meritorious Service Medal, Air Force Meritorious Service Medal with three bronze oak-leaf clusters, Joint Service Commendation Medal, Air Force Commendation Medal with one bronze oak-leaf cluster, Air Force Achievement Medal, Navy/Marine Corps Achievement Medal and Iraq Campaign Medal. He recently received a Legion of Merit award for his work as Exchange senior enlisted advisor.

Osby earned an associate degree in Computer Information Systems from the community college of the Air Force and a bachelor’s and master’s degree in Information Systems Management from Park University and Webster University, respectively.

Immediately before joining the Exchange, Osby served as squadron superintendent, 81st Diagnostic and Therapeutic Squadron at Keesler Air Force Base.

In a 2023 photo, Chief Master Sgt. Kevin Osby, the Exchange’s senior enlisted advisor, tours the Exchange’s Fort Knox Name Tape Plant. Teresa Green, manager of the Exchange’s Fort Knox Name Tape Plant, is his guide. Also pictured is Fort Knox Exchange General Manager Donald Basil and Name Tape Plant associate Pedro Medina.

Retirement—and other—plans

One of the last places Osby visited in his Exchange role was Vancouver Barracks, Washington, home of the first post exchange, established in 1895. (The Exchange still has facilities there, maintained by the Joint Base Lewis-McChord Exchange.)

“I remember one of my talking points was our first site being in Vancouver, Washington,” Osby said. “It’s kind of ironic that it’s one of the last sites I got to see as senior enlisted advisor. I got a chance to meet the two associates who run the store there. It was pretty awesome.”

As for his retirement plans, Osby talks about those with typical humor.

“I tell people my retirement plan is to attempt to grow a beard,” he said. “I don’t know what’s under the hood so I’m going to give it a month and see what comes out. We’ll go from there.”

More seriously, this September marks his 20^th wedding anniversary. “I think my wife wants to go on a trip,” he said. “So this is the perfect time to retire.”