EO Chicago Strategic Alliance Partner Spotlight: Jared Gibson

As a die-hard Cleveland sports fan, Jared Gibson knows a thing or two about solidarity. “Cleveland teams make up seventy-five percent of my wardrobe and my kids’ wardrobes,” he says, laughing. “It’s very rare that I miss an Indians, Browns, Cavs, or Buckeyes game.” Gibson’s love of sports and loyalty to Cleveland teams speak volumes about his personality.

As a die-hard Cleveland sports fan, Jared Gibson knows a thing or two about solidarity.

“Cleveland teams make up seventy-five percent of my wardrobe and my kids’ wardrobes,” he says, laughing. “It’s very rare that I miss an Indians, Browns, Cavs, or Buckeyes game.”

Gibson’s love of sports and loyalty to Cleveland teams speak volumes about his personality. He is the friendly fan you’d likely encounter at a game—high-fiving when the team scores and offering to pass your beer or hot dog from the vendor in the aisle—but it’s the solidarity that gives depth to his affability. He is genuine and supportive, qualities that align well with EmPowerHR, where he is the VP of growth and marketing.

“Our whole motto is, ‘Through authentic connections and relentless accountability we deliver what matters most to our clients,’” Gibson explains.

He is relatively new to EmPowerHR, having entered this role just over a year ago. (And what a year it has been!) However, to truly “meet” Gibson, the story starts further back in time.


His Rookie Years

Born and raised in Akron, Ohio, Gibson played baseball throughout his childhood. His love of sports grew even greater when, for three years in high school, he worked as a cotton candy vendor at Jacobs Field (now known as Progressive Field), where his beloved Indians play.

“It was back when we sold out every game—we were in the World Series a few times,” he recalls. “They basically paid me to watch those teams in the late ’90s. It was awesome.”

After high school, he attended the Ohio State University and earned his bachelor’s degree in sociology. He then moved to Cleveland and joined a startup company called the Spyglass Group.

“I had a buddy working at Spyglass, and I think I was the fifth employee hired there,” he remembers. “We worked directly with CFOs to help them reduce the telecom line item of their P&L. It was a small company. I fell in love with it, and with the people there.”

The company started growing fast, and Gibson’s trajectory grew at the same speed.

“We started hiring more salespeople,” he says. “I opened our first remote office down in Columbus, expanded our footprint into Southern Ohio, West Virginia, Western Pennsylvania. And I was a road warrior. I was basically driving two to six hours a day to go to meetings.”

It was this experience that refined his sales and networking abilities. As he puts it, “You scrape your knees when you’re out by yourself, and I learned a lot when meeting with different people.”

Soon, Spyglass asked Gibson to open its first out-of-state office in Chicago, and he jumped at the chance.


A Career Takes Shape

In 2010, Gibson moved to Chicago as a regional sales director with Spyglass. He spent just under four years growing the territory—covering Northern Illinois, Southern Wisconsin, and Northern Indiana—when he hit a crossroads.

“I was just drained from driving so much, and I discovered that the only way for me to advance any further would be to move back to Cleveland, where Spyglass was headquartered,” he explains. “And at that time, I had met my girlfriend, now wife, and she was staying in Chicago. So it was time for me to make a move.”

Gibson left Spyglass, and still looks fondly on his time there. “I was there for almost nine years—it was an awesome and fun ride, to be with a company through the ups and downs as it grew,” he says.

The experience instilled a passion in Gibson for small- and medium-sized businesses in growth mode. And after a few sales roles over the next five years, he found an organization that rekindled the passion he felt while at Spyglass.

“I interviewed with these guys at SnapMobile, part of CommonSail Investment Group, and they blew my socks off,” he recalls. “It was a real family feel, and it reminded me of my days back at Spyglass. I’ve been now with three CommonSail companies in about a year and a half—SnapMobile, Proof Works, and now EmpowerHR—and it’s been great.

“This team has really helped me see the value and excitement of living outside your comfort zone instead of just living in it,” he adds.

When he was moved to EmPowerHR, his role changed from strictly sales to also include marketing. He was charged with building the company’s entire marketing engine. He recalls thinking, “‘Challenge accepted. Let’s do it. As a salesperson, I will join the dark side and go over to marketing.’”



Gibson started his new outside-the-comfort-zone role at EmpowerHR in February 2020. He was gung-ho on building a new website, generating leads for the sales team, helping network at events, and more. Then . . .

“COVID hits,” he says. “I quickly realized I’m the only person in the marketing department, and marketing is also in charge of communication to our clients, who happen to be small business owners who are barely staying above water.

“I had to drop every preconceived notion that I had of what I wanted to do,” he continues, “and run to the fire of working with our HR team—working with all the teams—on understanding the new regulations and compliance, and make sure we were getting information out in a timely manner to our clients because they had questions. They didn’t know what was going on.”

Gibson recognizes that it was chaotic, but his trial-by-fire entry into EmPowerHR also fast-tracked his comradery with the team. It’s the environment of solidarity Gibson enjoys in his personal life, now manifested in his career, as well.

“I never would have built the relationships that I have with the entire team,” he says. “I feel like I’ve been here thirty years. It was a rough 2020 for everyone, but the world is opening back up, and as a company, we’re back above where we were prior to all of this starting—and we’re going to continue to grow.”


Re-emergence and EO Partnership

In the past few months, Gibson has been able to restart the projects he put on pause last year. And living outside his comfort zone has become second nature after being a member of the leadership team through the pandemic.

“I’ve never been on a leadership team before,” he says. “Now, I’ve been involved with helping make crucial decisions for the company—investments that I’m solely responsible for. Previously, I may have pulled back on some of those decisions. Now, I’ve got a good team motivating me, and there’s no holding back anymore. If we fail, we fail fast, we move on, and learn from it.”

In November, he also became the point person for EmPowerHR’s Strategic Alliance Partnership with EO Chicago. In the role, he’s bringing the firm’s expertise to local entrepreneurs in need of post-COVID guidance.

“What we’re seeing now is such a wide range,” Gibson says, “from compliance-related issues like new government regulations on vaccinations for your staff, to people issues with the mental health effects of COVID, to navigating the decision of if and when to bring people back into an office space. And diversity and inclusion is huge right now—we’re also putting programs in place for that.”

EmPowerHR’s expertise is paramount amidst today’s uncertainty, and Gibson’s personality drives home the firm’s fit as an EO partner. “I really love meeting people and building those authentic connections,” he notes. “The world is opening back up, and as more events become in-person, I’m excited to be at them, to build relationships and deliver what matters—not just to our clients, but to everybody.”

He adds, “To any EO member looking to fill a foursome in golf, please reach out to me. Anything outdoors—sports, concerts, skiing, events—I’m in.”


Call It Home

Just as Gibson’s role at EmPowerHR is normalizing, he’s also settling into a new home. He and his wife—who, as he proudly brags, is a partner at a Chicago-based law firm—are remodeling an old home in Highland Park, where they plan to raise their two kids: Gavin, who is turning three in June, and Riley, who “just turned five, going on thirteen,” he jokes.

His team spirit permeates throughout his life, including the upbringing of his kids. “It’s awesome to see them interact,” he says. “They obviously beat each other with random objects, but they stick up for each other, too. When it matters, they’ve got each other’s backs.”