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The Navy helped her find her voice; Microsoft helped her transform her career

For U.S. Navy veteran and Microsoft Software & Systems Academy (MSSA) graduate Jessica Helmer, building a career wasn’t an easy journey. Her road was fraught with setbacks, but she paved it with a determination to always learn and a refusal to ever settle.

Now, as a program manager with the Shared Services Engineering team at Microsoft, she can’t imagine a more rewarding career — or a more welcoming home.

Growing up in Point Blank, Texas, was challenging for Jessica. Her dad died when she was young. At times afterward, she, her mother and older brother had to skip meals. When they were “between homes,” they couch-surfed with family and friends. Even when her mom enrolled in college and they moved into campus housing during the school year, things never felt steady for Jessica. She was extremely shy and performed inconsistently at school. Through years of moving around, she tried to stay on track but eventually found herself failing out of college.

When Jessica did find a way to start attending classes regularly in her early 20s and earn decent grades, struggles at home once again threatened to throw her goals off course. So she made a plan: She would see her classes through finals. Then, she would enlist in the military.

During the semester, Jessica had connected with her stepdad’s secretary, who was married to an Air Force veteran. Their conversations inspired her, and she determined that military service could give her the stability she’d long craved — and more important, a sense of belonging.

Jessica at her first Hackathon.
Jessica at her first Hackathon event in July 2018, where her team supported the Agaram Foundation.

To put her plan into action, Jessica returned to Point Blank to visit the military recruiting centers. Within just three weeks, she had completed her paperwork, aptitude test and physical exam, and was headed off to Naval Station Great Lakes for boot camp.

To this day, Jessica recalls boot camp as the biggest mental and physical challenge she’s endured. Yet, it was a mostly positive experience because of the people looking out for her.

“Our Recruit Division Commander was like a father or a big brother to me — he wanted to make sure all the females were set up for success,” she recalls. “He gave us an idea of what to look out for in our male-dominant environment, and how to handle ourselves.”

As an electronic technician charged with maintaining communication and navigation systems, and the only female in her division of 35 people — and still extremely shy — success meant figuring out how to establish herself and prove she deserved to be there. It wasn’t easy.

“Some people doubted what I was doing or assumed I wasn’t smart enough, especially since it was technical stuff,” she says. “There was this mentality that women don’t do tech, they do nursing.”

The more she strived to do her best work and learn as much as she could, attitudes shifted. Still, Jessica felt continual pressure to prove herself. Doing so took a mix of figuring things out on her own and embracing guidance from de facto mentors. They pushed her when she wanted to settle. They encouraged her when she felt out of her element.

For instance, when she was in charge of systems during a power loss on the USS Boxer, tasked with keeping the ship afloat and in readiness, she successfully stood her watch.

“It was frankly terrifying,” she says. “But it was also a huge source of pride because I was young in terms of how long I’d been serving, and I was the only female that had done it.”

Her willingness to jump in and learn as she went served Jessica well throughout her 10 years of naval service. It’s how she turned a misassignment at the Fleet Anti-Submarine Warfare Training Center into a career opportunity, even though it meant learning a completely new set of skills, shifting from administering systems and networks to coding software.

“The captain straight-up told me, ‘Yeah, we messed up, you’re not the type of technician we need. But you’ve got this, you’ll figure it out,’” she says.

After being trained on the basics, she did figure it out. And she enjoyed it. Along the way, she gained another mentor: a senior systems engineer who regularly came out to help her with repairs.

So when the time neared to consider re-entering civilian life and Jessica discovered MSSA, she felt the program, designed for military veterans and transitioning service members, was a natural next step.

Jessica poses with the Halo 2 Master Chief.
Jessica poses with the Halo 2 Master Chief after her first Microsoft interview in September 2017.

Jessica attended the 18-week MSSA Cloud Application Development course in San Diego, where she learned database programming and other skills for building and maintaining modern applications. As a graduate, she was also guaranteed an interview for a full-time job at Microsoft or one of more than 360 hiring partners.

When her official transition date neared while she was still in the interview process, Jessica went into hyper-drive. She split her days between applying to jobs and taking online courses to deepen her technical knowledge, all the while remaining hopeful and determined that her efforts would pay off. They did.

After several rounds of interviews, including one in which she had follow-up meetings with two separate groups at Microsoft, Jessica accepted an offer from the team that had been urged to consider her for the role by her MSSA mentor.

“I think the interview process speaks to Microsoft’s desire to find the right fit,” Jessica says. “For both the hiring team and the person they’re bringing in.”

Now, she’s a program manager working on the back end of the systems that enable Microsoft to build its products. Her team is “the backbone of the company,” as she puts it. And she’s proud to be right in the mix of it all, coordinating and translating information between nontechnical customers and highly technical engineering teams.

It’s still mind-blowing to this Navy veteran that she has a successful career in tech, working for a company she admires. She credits her success to the military and MSSA, and especially the support network she’s developed.

“I’m so impressed that the military and Microsoft teamed up,” she says. “To me, growing up, the idea of being a software developer was like this magical thing that only the most special people could do. But here I am. It’s obvious that my Microsoft team wants to help me to be the best that I can be, and therefore make our team the best it can be. It’s been a fantastic transition process for me.”