When reflecting on his career, Derek Kissos attributes many of the opportunities in his life to strong leaders, good mentors, a passion for mission and unexpectedly, golf.
Kissos is the industry lead for the Global Defense & Intelligence business at Appian Corp., a software development company headquartered in McLean, Virginia. His career, however, began in the U.S. Army after professional uncertainty in college.
He grew up in Ohio loving sports, attended Ohio State University like his father and at first, thought about being a sports agent or lawyer.
“I didn’t really know what I wanted to do, so I just chose the path of business,” Kissos told WashingtonExec. “It gave me a lot of leadership skills.”
In 2005, still unsure of what he wanted to do professionally, he decided to join in the U.S. Army.
“I was the first on either side of my family to enter the military,” Kissos said.
He began his career at the Army installation in Fort Jackson, South Carolina, working in personnel management and human resources.
He then served as an assistant personnel strength manager and HR specialist with the 25th Infantry Division at Schofield Barracks, Hawaii, from February 2006-May 2008, processing and analyzing personnel actions for more than 10,000 soldiers. During this time, he was deployed to Iraq for 15 months during Operation Iraqi Freedom.
“I handled every communication that would come out of Congress, be it a senator or your local politician, while managing where the troops within our area of operations on the battlefield,” Kissos said. He was the lead communicator handling all congressional inquiries when dealing with soldiers’ quality of life, pay and so on.
Kissos was also quickly learning being a good leader means being well rounded, which is key for anyone in a position of management, and leaders in his life helped him get there.
“I’ve been really lucky to have great leaders above me who’ve kind of guided me and let me identify what I’m good at,” he said
One of those leaders was his boss during deployment, Lt. Col. Liana Bratland.
“She really said, ‘Look, you’re good at what you do, but you really have skill sets that kind of transcend in the HR personnel world,’” Kissos recalled.
So, after Iraq, he was stationed in Hawaii as a company grade assignments manager for the U.S. Army Pacific Command, where he developed a system for placing the right officers in the right jobs across the Pacific theater.
Then, Bratland helped Kissos get a position at the Pentagon — one many applied for, but thanks to guidance and recommendation from his leaders, Kissos got.
In 2009, he became a strategic analyst and administrative manager for the Army’s Executive Strategy Group in the Office of the Chief of Staff at the Pentagon. He was there until March 2012 — over the course of three Army chiefs of staff — managing administrative operations and providing strategic analysis for a division of senior military officers and civilian strategic planners.
“I think this is the place that really kind of formed my career going forward,” Kissos said. “It was myself and four other colonels. And we did all the short-, mid- and long-term planning for the chief of staff.”
And along with strategy work, his team was responsible for short notice task forces. During the 2009 Fort Hood shooting in Texas, when Army major and psychiatrist, Nidal Hasan, killed 14 people and injured more than 30 others, Kissos and his team stood up a task force to assess all emergency response and security force postures for every base in the continental U.S.
“What was cool about that is I got to see kind of on a massive scale how a big program is led,” Kissos said. “We had different personalities, we have different missions and we had to put all that together to create a report back up to the secretary of the Army.”
Kissos was also reviewing and analyzing think tank events and products, providing a summary to senior personnel on the Department of the Army staff.
And though Kissos had planned on spending two years or so at the Pentagon and switching into an officer role, he quickly noticed as he worked with more and more government contractors, it would be difficult to get back into the “regular Army.”
“I typically wore a suit and tie to work because a part of my role at the Executive Strategy Group was to attend all the think tanks in D.C.,” Kissos explained. “I would be there interacting with industry. And I quickly just developed a love for it.”
And during this time, Kissos was also a charity golf tournament director. He coordinated and managed the annual Lieutenant General Timothy J. Maude Foundation Golf Tournament, which honored the highest-ranking U.S. military officer killed in the Sept. 11, 2001, attacks at the Pentagon.
And after a 9-year military career, it was at this golf tournament Kissos found an opportunity in industry.
From Golf to GovCon
Because he ran this charity golf tournament and worked with sponsors, Kissos got to know a few leaders at systems integrator Serco really well.
Soon enough, he snagged an interview at Serco — and where he ended up in the company, he also attributes to a strong leader.
Kissos was originally preparing for a role at Serco supporting the Army but during the interview process, he also sat down with the then-Senior Vice President of Federal Civilian business group Michael Plymack.
“This is another one of the key leaders in my life,” Kissos said. “And he ended up saying, ‘You know what? I don’t want you for that role. You’re going to come work for me.’”
Even though the civilian market was outside of Kissos’ comfort zone, Plymack pulled Kissos into that direction. Kissos joined Serco as a business operations manager to help run civilian business in 2012.
“That was my first foray into kind of jumping into the fire and seeing how operations are done at a pretty large scale,” Kissos said. “Mike ran about a $600 million portfolio that all of a sudden I was thrown into the fray working with their senior leaders, and how to manage that business.”
Kissos also served in business development for Serco’s health care solutions when the company entered the health care market after effectively doing so in the U.K. and Australia. He spent time with colleagues overseas becoming an expert in how to make hospitals operate more efficiently on everything nonclinical. After standing up the U.S. health care business, he was responsible for building it out.
By the time he left Serco in October 2015, Kissos was director of strategy and solutions, having moved into corporate strategy after health care.
“At Serco, I held three positions, each time being about 18 months in each, which again was great because I have great leaders around me who just kind of kept tagging me to do other things,” he said.
When Plymack decided to leave Serco, Kissos began thinking about his own next steps.
“One of the gaps I had in my professional experience is sales. And all the corporate leaders that I had worked with basically said: ‘You got to learn how to operate. You got to come up with a plan, and you also have to sell,’” Kissos said.
He left Serco to sell big enterprise resource planning packages at enterprise software company IFS in 2015, and served as director of operations and strategic development.
“I had no software experience, no sales experience, and they threw me in to lead their defense sales to government contractors,” Kissos said. “So, basically the Lockheed Martins of the world, the folks who make helmets for the F-35s, to basically sell them on ERP.”
Kissos helped generate the entire go-to-market strategy for defense, while also focusing on key and strategic accounts in selling software.
But ultimately, a sales job wasn’t conducive to starting a family.
“Life gets in the way,” Kissos said. “Where you’re doing well, you’re progressing, you’re a great salesperson, but then all of a sudden, you get engaged. And you get married and you start to have a family. And I couldn’t be doing the traveling two weeks out of every month anymore.”
A former peer at Serco Kissos had kept in touch with was running the Global Public Sector industry at Appian and connected Kissos with a new job.
“As Appian was taking a look at how to really grow in the defense market, I was lucky enough where, again, they tagged me to come and figure that out,” Kissos said.
He joined Appian in June 2018 as director of strategic capture for the federal market, and rose to his current position of industry lead of global defense and intelligence programs in May 2019.
“It’s the culmination of — I learned how to operate and develop a strategy and bring capability, then I learned how to sell, and now I’m going to bring both those worlds together in this role.”
And the role was new for Appian, created for Kissos. Once he helped stabilize how Appian did business development across the federal business, he began running the global defense portfolio.
“I love that I’m back to my DOD roots,” Kissos said. Because from the Army to industry, Kissos has always been driven by mission, he said.
“Being a former soldier and now basically providing a service and a capability back into the global warfighter community, it’s that mission. I was passionate about the mission when I was in uniform, and I’m almost more passionate about it now,” Kissos added. Now, he’s able to provide those protecting the country with software and capabilities that make their lives and jobs easier, ultimately impacting the country and citizens.
“That’s what gets me up every morning,” he said.
Coming Full Circle
Kissos said he’s heavily focused on building the brand of Appian in 2020, because it’s Appian’s legacy that ultimately drove him there.
“We’re a 20-year-old company, but we’ve always been headquartered in Northern Virginia. Which is really rare for a public software company,” Kissos said. “Appian cut its teeth in the Army.”
One of Appian’s first customers was Army Knowledge Online, a portal for all Army personnel in uniform or civilian.
“That’s the way I communicated with my parents when I was in Iraq. I was able to chat with them through AKO while I was overseas. And you know, I never knew it was Appian,” Kissos said.
He didn’t find out it was Appian until he began working for the company, and that’s something Kissos admired — as Appian grows, it remains humble.
“Because we’ve written every line of our software in the U.S., and I think we’re perfect for Department of Defense,” he said.
So, one of his main priorities in 2020 is getting out in industry and telling Appian’s story, and finding ways to collaborate with the government.
“I’m not just looking to sell you software; I’m looking to sell you an outcome,” Kissos said. “Because it’s not a transactional nature. Myself and our company cares about the mission and we want to make sure there’s success, not just a financial transaction.”
And in the future, Kissos hopes to make Appian the de facto low code platform for defense agencies, and as the global defense portfolio grows, he’s along for the ride.
“This is, for the first time in my career, a position where I’m not worried about what’s the next rung on the ladder. To me, it’s how effective are we being in driving capability across the global warfighter,” he said.
Kissos doesn’t do what he does for the financial or hardware awards, or the military pins — he does it for the success stories and personal stories from customers or colleagues, and the occasional “thank you.”
And ultimately, he does it for his family — his wife, his almost 2-year-old daughter and his son on the way.
“What motivates me to get there is, I want to do what my parents did for me, which is provide a pretty good life for my family,” Kissos said. “The only way I do that is if I’m a value to our global defense customers.”
So, he focuses on how to drive value, and how to be a good leader at work and at home.
“That’s really what it is for me. It’s the people and the impact you have on their lives,” Kissos said.
But he couldn’t have gotten to where he is today without developing as a person in the military, trusting his instincts and trusting the people around him who believed in him.
“I think if I wouldn’t have had the leaders I had, there was zero chance I am where I am today and I don’t think I’d be successful,” he said.
Some of that credit, however, is given to his love of golf. Kissos is a passionate golf player, but it wasn’t until the Army he really got into the sport. He had a lot of free time during his first duty station in Hawaii, and one of the Marine Corps bases there had a beautiful golf course. Now, he tries to get on the course once a week, but he doesn’t forget where it all began.
“If I didn’t learn to play golf there, I never would have ran that charity golf tournament while I was in the military and I wouldn’t have started in GovCon,” Kissos said. “So besides leaders, I guess you could say golf helped my career a lot, too.”