Spotlight: Randy Lovelace

From Boston Tech to KC Impact: How Randy Lovelace Found His Way Back (and Forward)

Each fall, Back2KC brings together former Kansas Citians who’ve built their careers elsewhere—but might still feel that tug toward home. Our goal? To reconnect them with the city they once called home—and remind them just how much opportunity exists here.

Attendees leave inspired. Many, like Randy Lovelace, actually come back. And when they do, they bring with them years of experience, leadership, and fresh perspective that only strengthens our region’s momentum. Here’s to sharing their comeback story and watching the positive impact they’re already making in and for KC.

When Randy left Kansas City years ago, he wasn’t sure he’d ever return. A Prairie Village native with big ambitions, Randy had his sights set on the East Coast—first for college, then for a career in technology that would take him to Boston and New York.

“I always loved Kansas City,” Randy said. “But when I was growing up, it was a different place. The suburbs were great, but downtown didn’t feel like a place where innovation was happening. If you weren’t in banking, law, or real estate, it was hard to imagine building a tech career here.”

After building an impressive career in tech—most notably at HubSpot, where he helped scale operations at one of Boston’s most well-known SaaS companies—Randy and his wife began asking a familiar question: What’s next?

“We were looking to buy a place, weighing our options between Boston, New York, and even Maine,” he explained. “That’s when my wife said, ‘What about Kansas City?’ At first I thought, I didn’t think I could excel at work here. But the more we explored it, the more it felt like the right move.”

Rediscovering KC—and Building a New Chapter

Randy made the leap, moving back to Kansas City in a remote role. Shortly after, a chance meeting with Darcy Howe led him to Back2KC.

“It wasn’t the reason I came back—but it absolutely reinforced that I’d made the right choice. Back2KC was the first time I felt the tech energy in KC in a real way. It’s been a touchpoint for me ever since.”

Now, Randy leads a sales team at SafetyCulture, a global tech company that chose Kansas City as its U.S. headquarters—a move Randy remembers watching unfold back in 2019, when the company spoke at the 2nd annual Back2KC event. “It’s surreal,” he said, “to now work here and help build the very future I once sat in the audience to learn about.”

Why Kansas City Works

For Randy, Kansas City offers the best of both worlds: a growing tech ecosystem and a deeply rooted sense of community.

“If you want to live the American dream—buy a house, raise a family, have a meaningful career—Kansas City is one of the few places where that’s truly possible. It’s financially approachable, culturally rich, and full of opportunity.”

And while Kansas City’s tech scene isn’t as deep as coastal hubs, Randy sees its trajectory clearly. “We’re not saturated yet, and that’s actually exciting. The companies are here. The talent is growing. It’s a patchwork that’s coming together—and Back2KC is one of the threads weaving it all in.”

Finding His People

When asked how he found his people after moving back, Randy is honest: “If you come to KC expecting to find your exact replica of a coastal tech circle, it may take some adjusting. But if you come looking for community, for people who open their arms and bring you in—you’ll find it.”

And he has. From reconnecting with leaders like Darcy to partnering with local organizations, Randy has found a rhythm that fits: balancing leadership, mentorship, and the desire to give back.

Looking Ahead

Randy’s not done building.

“My personal goal is to grow as a leader in Kansas City’s tech space. Right now, with two little kids, I’m focused on work and family. But as they get older, I plan to engage more—speak at events, mentor up-and-coming professionals, and help shape the next chapter of KC tech.”

His advice to anyone considering the move?

“Don’t overthink it. You can still work remotely. You can build an incredible life here. You’ll find community, opportunity, and space to grow—personally and professionally.”

Randy may have left Kansas City for opportunity, but he came back for something even bigger: impact.

Want to connect with Randy?

He’s always open to talking tech, leadership, or returning to KC. Connect with Randy on LinkedIn.

Randy’s journey is exactly why Back2KC exists. When talent returns, cities grow. When knowledge comes back home, ecosystems thrive. We’re proud to highlight stories like his—not as isolated wins, but as proof that investing in relationships, community, and reconnection works. As we gear up for our 8th annual Back2KC event on September 19, we’re excited to welcome more returnees, more builders, and more leaders like Randy—people who aren’t just moving back, but moving KC forward.

Be sure to check back next week as we spotlight more wonderful Kansas Citians doing innovative work in and for our community!

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