Veterans find success in military service and Montana’s tech sector

“I wasn’t looking in Montana,” Ryan Castonia, a principal at Two Bear Capital, said. “But by having that network, having the discussions about what was important to me and what I was trying to do, that ultimately led to my post military career, an amazing opportunity that I never would have found on my own.” Photo courtesy of Castonia.

By Emily Simonson

Desireh Kissinger has lived in Montana all her life. A Missoula native, Kissinger graduated from the University of Montana with an Associate of Applied Science in Network System Administration and Security in 2017. Now, she has temporarily traded the view of Mount Sentinel from her office with Alter Enterprise, an IT company founded by Ryan Alter in Missoula, for the green mountains of Poland. 

Since 2010, Kissinger has served as an IT specialist for the Army Reserve and left on her first deployment last September. While she misses the home she has found with Alter Enterprise, she’s not worried about missing out on new opportunities for professional growth while she’s overseas. 

“Everything that I’m doing while I’m here is still going to benefit me when I get back,” Kissinger said during a video interview.

“I’m really proud of the time I have spent in the military,” Desireh Kissinger, an IT specialist at Alter Enterprise, said. “I love both my jobs and I appreciate my civilian employer’s willingness to adjust schedules and projects for my military service.” U.S. Army Reserve photo by Maj. Olha Vandergriff, 652nd Regional Support Group.

It’s no accident that Kissinger is an IT specialist in both the military and at Alter. With veteran parents, she knew when she enlisted out of high school how to make military service work for her ultimate career goals. 

Kissinger found and stuck with a supportive employer, leveraging an internship at Alter into a full-time job after graduation. She earned certifications in A+ and PC Pro – transferable credentials that increase her value to both the private sector and the military. Kissinger has been planning her deployment for years, giving her employer plenty of notice and time to prepare. 

Beginning a deployment or leaving the military can be a challenging transition, but many veterans and current service members, like Kissinger, find success in Montana’s thriving business and technology communities. We spoke to a number of Montanans – tech employees, entrepreneurs, and executives – about their best advice for transitioning into technology and the Big Sky State.

Think about Transitions

Marketing Manager James Rolin, right, shows tourists an egg tray at the Cowboy Cricket Farms facility in Belgrade. Photo by Rachel Lethe/Bozeman Daily Chronicle.


In 2006, James and Kathy Rolin left the Coast Guard together to raise their family. They struggled to find the right fit for several years, bouncing from Michigan to California with their two daughters in tow. In 2015, James joined the Montana National Guard, and the family settled in Bozeman. 

“It’s the only place we haven’t wanted to leave yet,” he said. 

In 2016, the couple founded Cowboy Cricket Farms, an edible insect farming company that plans to leverage AI technology to empower independent farmers.

The Rolins’ military experience was surprisingly helpful with starting a new chapter in their lives, James said. 

“The military teaches you to do a lot with a little,”James said. “To be comfortable with failure, to not sleep a whole lot. So it is a perfect recipe for an entrepreneur.”

Ryan Castonia, a principal with Two Bear Capital, also struggled with his transition at the end of a 14-year career in U.S. Air Force Special Warfare. From the age of 18, Castonia said he developed skills through some amazing opportunities, including several deployments to Afghanistan, Turkey, and Germany, and being a member of the team who founded the Department of Defense’s Joint Artificial Intelligence Center at the Pentagon. But it still wasn’t enough to prepare him for the civilian workforce. 

“Here I was at 31, married with two kids, on the first job search in my life, and didn’t really know what the next step looked like,” Castonia said. 

Castonia struggled for eight months to find a career that fit for him. He knew he wanted to make a difference in the world in a way that utilized his MIT education and experience as a special warfare officer, but also provide stability for his family. His strong network of friends from college and the military paid off in early 2019. A fellow veteran pointed him in Two Bear Capital’s direction, a venture capital firm out of Whitefish founded by Mike Goguen.

Castonia had some initial reservations, fearing venture capitalists to be like old-time Hollywood villains stealing entrepreneurs’ money. But it only took one phone call with Goguen, and Castonia was blown away. Not only did they share things in common like being from blue collar families, but they shared a drive to make the world a better place. 

A few months later, in April 2019, Castonia made his way to Montana, still skeptical but open to an opportunity to make a strong impact on the world. After experiencing almost a year of uncertainty, Castonia speaks from experience when he said other service members should start thinking ahead of time about their post-military plans. 

“I think that it would be good for all service members to realize that you are going to leave at some point,” Castonia said. “Most people wait too long to really invest the time necessary to make sure you have a successful transition.”

Build Transferable Skills

Ryan Castonia, a principal at Two Bear Capital, sits inside an Italian helicopter flying near Cervia, Italy during training with the Italian rescue forces. Photo courtesy of Castonia.

Taking advantage of built-in opportunities can make the soldier-to-civilian transition easier. For example, most commands offer the chance to get certifications, which make it easier to translate specialized military skills into more digestible civilian terms on a resume. Many veterans can attest to how hard it is to translate military jargon to civilian employers. 

If you work with your command, James said, there are often certification programs that apply to the field you want to work in after service. If a service member knows the field they want to go into, they can start getting certified years before leaving the military.

“A lot of employers are looking for the certification, the specialization within a special niche in that industry and the government,” Joel Pineiro, Chief Operating Officer at Ascent Vision Technologies, said. 

Pineiro knows how important military certifications are in the civilian world. He knew he wanted to serve in the Marines when he was 17, but at the behest of his father, Pineiro went to college first. And he’s glad he did. 

I’ve gone to college, and I’ve held different job roles in different industries,” Pineiro said. “I was well-prepared [for the civilian world] before I joined the Marine Corps.”

This prior experience taught him the language private sector businesses use, like listing the soft skills involved in military leadership as experience. 

“You’re in charge of leading [service members],” Pineiro said. “In the civilian market, you are a manager or supervisor in charge of supporting and ensuring that your employees are performing their jobs.”

Castonia added that he had the opportunity to be a leader with the military much faster than peers in the private sector. 

Find Personal and Professional Support

Chief Operating Officer Joel Pineiro, fifth from the left in the back row, and his team pose for a picture on their annual Ascent Vision Technologies Team Hike. Photo courtesy of K Mita, Cerakote Specialist and Digital Media Manager at AVT.

Like Castonia, Pineiro found his home in Montana through networking.  

For many, moving is a side effect of military service, but moving to Montana is an opportunity Pineiro would not have had in the Marines, since there is no active Marine component in the state. Throughout his career, Pineiro has been stationed mostly on the east coast. 

Pineiro connected with Tim Sheehy, founder of Ascent Vision Technologies and Bridger Aerospace in Belgrade, Montana, through a mutual friend who’d served with both men at some point in their military careers. Pineiro consulted remotely for Sheehy for several years before moving to Montana in 2017 to head operations including Ascent Vision, which specializes in gyro-stabilized imaging systems and fully integrated solutions for counter UAS, air defense, and ISR (intelligence, surveillance and reconnaissance). Like other military families, Pineiro has quite the list of former addresses; while in Montana, he marked his 32nd. 

Networking to help job search can be useful for a successful transition, but a strong personal support system is a necessity. James said the struggle of leaving the military was lessened by sharing the experience with his wife. 

“There’s so many people that get out and it’s just them,” James said. “But if you have that group, whether it’s your spouse, or a friend or someone else, it helps.” 

James advised finding a support group upon getting out of the military, such as Bunker Labs. Bunker Labs, founded in 2014, is a non-profit organization that helps veteran and military spouse entrepreneurs start businesses. 

“We have a chapter in Bozeman and they’re amazing,” James said.

The Rolins also recommend Operation Code, a non-profit that helps veterans learn software development. The COMMIT Foundation, which helps exceptional veterans and service members transition into civilian roles and provides resources for companies hiring veterans, is another resource veterans can use.

The military also offers transitioning officers assistance through the Transition Assistance Program (TAP), but Pineiro said it’s only a starting point. 

They did a good job of just generally giving people ideas of what are the things that you need to keep in mind when transitioning from military to civilian,” Pineiro said, adding that TAP can be a little too broad. 

Castonia found specific organizations, like Elite Meet, tailored to his branch and job to build off TAP. There are so many options when it comes to veteran support, Castonia said.

Kissinger knows all about support. Kissinger’s civilian job will be waiting for her when she gets back. Ryan Alter, founder and CEO of Alter Enterprise, said he understands how important employers are to supporting personnel in the military Reserve. 

“You have to be flexible,” Alter said. 

Kissinger’s nearly year-long absence has been an adjustment for the team. Her coworkers miss her and are taking care of the plants on Kissinger’s unoccupied desk, Alter said. 

“It’s always a team effort in the military,” Kissinger said. “One of my favorite things about Alter Enterprise is the emphasis on the team, everything we do revolves around the team just like in the military and I just love that. I miss my team.” U.S. Army Reserve photo by Maj. Olha Vandergriff, 652nd Regional Support Group.

Alter didn’t know much about the military, he said. Kissinger’s deployment has been a learning experience for everyone. The team prepped for months before Kissinger’s departure, wrapping up her assignments and training other employees to fill her role. Alter said he does not view this deployment as a hindrance on his business and assures other employers that a year-long absence is nothing to be concerned about. 

“It’s a small price to pay for an amazing team,” Alter said. 

Kissinger is still trying to make herself a better team member almost 5,000 miles away. While deployed in Poland for the next nine months, she plans to get two more certifications in security plus and project management. 

“I’m in the situation where my two careers are the same,” she said. “It makes it really easy to kind of keep them connected.” 

With the certifications and experience she will get after this deployment, Kissinger is positioned to move into a more official project management role when she returns to Alter Enterprise.

To other service members seeking to make a life in technology, Kissinger recommends they “find a way to make it so that it’s not a chunk of your life that is disconnected or wasted… Make it an experience that benefits the other side of your life.”

About the Author: Emily Simonson is the staff writer and content creator for the Montana High Tech Business Alliance. Originally from Havre, Emily will graduate from the University of Montana with a degree in English in May 2020. She is also a Public Affairs Specialist in the National Guard and enjoys reading and knitting in her spare time.

About the Publisher: Launched in 2014, the Montana High Tech Business Alliance is an association of more than 230 high tech and manufacturing companies and affiliates creating high-paying jobs in Montana. For more information visit

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