How One Unpaid Intern Rose To Become President Of Top Cybersecurity Company

In 2002, Jason McGinnis talked his way into an unpaid internship at the company that would become SilverSky. Today, he's the President of the Morrisville-based cybersecurity firm that has hundreds of employees worldwide.

When Jason McGinnis convinced SilverSky’s CEO Richard Dobrow to give him a chance and hire him as an unpaid intern some two decades ago, he could never have imagined he’d one day become the president of the Morrisville-based cybersecurity firm.

In fact, it was never in McGinnis’s plans to join the IT world at all. Growing up in northeast Arkansas, he planned to become a doctor ever since he was 6 years old. But during his pre-med track at the University of Arkansas, though, he fell out of love with medicine, and IT had always been there waiting for him.

McGinnis’s first job in high school and into college was working for Walmart as a mainframe operations analyst. And after moving to south Florida to be with his wife, with no set job or plan, tech again appeared as the ideal option.

McGinnis bounced around from roles at EDS, American Express and IBM. At IBM, he was part of a program that allowed employees to earn their Master’s while working.

During a class, McGinnis met a teacher who would change his life. Richard Dobrow, the CEO and Founder of Guarded Networks (which would turn into SilverSky), was not even supposed to teach the cybersecurity course at Florida International University (FIU). There was a last-minute instructor cancellation, but in some ways, it may have been fate.

Because it was during that time that Dobrow and McGinnis became good friends. Upon receiving his Master’s in Management Information Systems from FIU in 2002, McGinnis asked if he could come work for him.

McGinnis went out on a limb: he told Dobrow he didn’t have to pay him, just let him spend two days there a week and learn from the company. Dobrow agreed, starting a chain of events that led to McGinnis serving as president of the firm today.

As an unpaid intern, McGinnis said he walked into a small startup that was—relative to the larger corporations he had previously been a part of—in complete chaos organizationally. The second day there, McGinnis began running operations and creating a structure that worked based on his experiences at Walmart, American Express and IBM. Three months later, Dobrow said it was about time to offer McGinnis a real job.

Jason McGinnis

While McGinnis objectively took a risk by working for free for the early cybersecurity startup, it paid off. He was inherently attracted to the cybersecurity field, but even more than that, McGinnis discovered that working within a small company where you can truly make an impact was where he wanted to be.

“It was a lot of fun for me coming from the really big, stodgy businesses that were amazing businesses but you kind of felt like a number,” McGinnis said. “You went in, you did your eight hours… Starting in a small company like that, it just gave me this excitement. You wear 15 different hats, and you’re empowered to go do whatever you need to do.”

McGinnis moved on to senior roles at Raleigh-based NeoNova Network Services from 2008 through 2021. Meanwhile SilverSky was acquired by tech giant BAE Systems in 2014 for $235 million.

But in late 2020, Dobrow put together a team of SilverSky execs with outside financing from SQN Venture Partners to buy back SilverSky. Shortly after, Dobrow called McGinnis back to be the president and COO of SilverSky. Since then SilverSky has been on a growth and acquisition tear, making headlines for acquiring tech companies Cygilant and Cybraics, among others.

From this career journey, McGinnis encourages other young professionals to view hard work not as something to avoid and instead as an investment into their futures, like he did with his unpaid time at SilverSky.

“I think so many people today are, especially in school, there’s expectations and entitlement that I don’t think is right,” McGinnis said. “I think people should really want to roll up their sleeves, dig in and go above and beyond—because they’re investing in themselves. And by doing that, they also get an opportunity to be part of building something and seeing something grow.”

Moving to the Triangle

SilverSky originally moved to North Carolina in 2007 after years of operating in south Florida. The transition came in part because of an acquisition here as well as several years of hurricane disruption to the team.

Naturally, there are many benefits to relocating to one of the nation’s top growing tech hubs. For one, McGinnis said Silversky’s relocation into the Triangle enabled them to take advantage of the talent pipeline from universities like UNC, NC State and Duke.

“They bring a skill set because of the environment and an eagerness to learn,” McGinnis said. “So we certainly leverage that.”

While SilverSky has grown well beyond the small, gritty tech startup it was when McGinnis first became involved, he urged young professionals to be comfortable taking calculated risks in their careers. These might include joining a startup or choosing a job in a field you hadn’t always planned.

“You have to be willing to step out of your comfort zone and try something,” McGinnis said. “Because if you don’t, you’ll never learn. It really is about challenging yourself.”

McGinnis also said that surrounding himself with people who were in positions he aspired to was important in his own career trajectory.

Jason McGinnis (center) is a leader of Hope Reins, a Raleigh-based nonprofit that pairs rescued horses with kids who have suffered trauma.

When it comes to SilverSky’s growth from an early 2000s tech startup to a mega cybersecurity firm with hundreds of employees worldwide, filling in the gaps of the cybersecurity needs for small- to medium-sized businesses has been the name of the game. 

But the industry is undergoing significant changes: perimeter security is much less profitable, and AI-driven solutions are a leading force, McGinnis said. To stay on top of these trends, SilverSky has proven itself as a company that can make strategic acquisitions and keep growing.

“All the acquisitions really play into, how we can expand the capabilities that we have to serve our customers,” McGinnis said. “We joke about world domination. We want to be able to serve our market not only in the U.S. but internationally.”

Outside of work, McGinnis has also made a name as a nonprofit leader for Hope Reins. Raleigh-based Hope Reins pairs hurting kids with rescued horses to find hope and healing after experiencing trauma. McGinnis and his wife stumbled into the nonprofit after adopting their daughter, who was 11 at the time, around a decade ago.

In a way, McGinnis can look at both his work for Hope Reins and in running SilverSky as ways to ultimately make a positive impact in the world, whether it be for businesses looking to protect themselves and their employees, or children overcoming adversity.

“There’s a huge mental health crisis, and we think it’s certainly gotten worse,” McGinnis said. A global pandemic, isolation and overarching worldwide conflict will do that, and adults aren’t the only ones suffering. “There are so many children who have mental health issues that are not being treated or not being served. This is a way to feel like we can actually make an impact in children’s lives on a regular basis.”

About Suzanne Blake 362 Articles
Suzanne profiles startups and innovation for GrepBeat. Before working at GrepBeat, Suzanne attended UNC Chapel Hill, obtaining a degree in journalism and political science. Previously, she wrote for CNBC, QSR Magazine, FSR Magazine and The Daily Tar Heel.