A Career Defined by Craft, Connection, and the Courage to Keep Going

In October 2024, Stephen Jacobson was thinking about his own father, a man who retired at age 65 and lived to be 89, enjoying a long and fulfilling retirement for nearly twenty-five years. When Jacobson announced his own retirement, after almost two decades at Hilton, he thought he might enjoy the same. It lasted about two months.

Actually, it lasted about twenty minutes. The same day the former VP and senior director of Hilton Grand Vacations and current VP of construction at Highgate announced his retirement, he got four job offers.

“I got my feet under me, I visited my daughter, and while I live on the Big Island [Hawai’i in Hawaii], most of my friends don’t,” Jacobson recalls. “I wasn’t playing golf and keeping up with things the way I was used to, and, from what people tell me, it just might not have been time for me to give up my whole career just yet.”

You don’t get the feeling Jacobson has given up on much in his life. His presence, even over a video call, makes you think of an old movie star. There is a gravity and presence to the VP whose project delivery victories have spanned hospitality, transit, retail, oil and gas, and pharmaceutical and cosmetic packaging. When you talk to Jacobson, one feels an immediacy. He jokes this may be because people in his field are used to half-committing to any deadline. But it’s more than that. Stephen Jacobson feels like a force.

This may be why Paul McElroy, EVP of design and construction at Highgate, immediately came after the veteran. The two had known each other for decades but never worked together.

“‘Just come have fun with us,’” was the pitch, Jacobson says. And what the un-retiree found was a team whose energy and cohesion mirrored his own values. He wasn’t searching for an easy job—he was searching for the right job.

“There are a few things I haven’t had the opportunity to do in my career,” Jacobson says. “I want someone to hand me an Olympic Village job. I want to build everything from the stadiums to the residences. I’ve never built a stadium, and I’ll you, I want to build a big one.”

What Highgate has gained isn’t just technical skills or industry experience. It’s an unwavering focus on people and relationships. Jacobson stands by a belief that was honed by early mentorship in his own career: You don’t lead or manage teams. You lead and manage people. John Creel at BP was an early source of inspiration for Jacobson who provided him a lifetime of mentorship in a handful of years. It influenced his own belief and value in investing in others’ growth.

“Building teams is something I pride myself on,” the VP explains. “The more you can communicate and be clear about what you’re working toward, the more importance and pride people can have in what they’re doing. Your people have to understand the deliverables, in what they’re expected to do, and why they’re doing it.”

The VP advocates for ongoing education, professional qualifications, and volunteering with industry organizations, like the Association for the Advancement of Cost Engineering (AACE). Jacobson has been a committed board member and member of the organization since 1986.

That focus on people and connecting through organizations has ensured Jacobson hasn’t had to look for the majority of his career. It also landed him accommodations from the Hawaii General Contractors Association who recognized Jacobson as an industry partner in 2020.

Succeeding in Hawaii is its own victory, one that takes time, and an incredible amount of trust, the VP says.

“This is a small market, and you can’t go throwing away relationships if things don’t go the way you want them to,” Jacobson explains. “It’s also a market where people want to develop a relationship before they work with you. Trust is a big deal here. About half the people that move here leave in the first two years. We’re just far from everything here and not everyone is ready for that. That also means people don’t want to invest in a relationship if they don’t think you’re going to be here for the long haul.”

There is no job or role that comes up for Jacobson more so than his own daughter, now fully grown and enjoying a successful career of her own in Vancouver. The VP refers to her often, almost as a lens for how he sees the rest of the world. When this is pointed out, Jacobson offers the only real advice he feels comfortable giving those in his own industry.

“For the bulk of my career, I was traveling 85% of the time,” Jacobson said. “Don’t do what I did. I have spent a lot of time regretting what I missed. And I am very fortunate to have an incredible relationship with my brilliant daughter today. But I missed so much. And I always tell others not to do what I did.”

This is the hardest part of loving what you do, Jacobson says. He doesn’t really feel like he’s worked a day in his life, but finding the balance with the rest of his life took too long. But at this stage of his career, Jacobson has the perfect balance of everything he’s looking to do, and, more importantly, everything he already has.