From Brushstrokes to Billboards: The Story Behind Keystone Outdoor

It’s hard to imagine today, but there was a time when every billboard was painted by hand.

Long before digital displays, vinyl installations, and computer-generated artwork, billboard painters climbed towering structures with buckets of paint and oversized brushes, creating advertisements one letter at a time.

That’s the industry Dominick Cipollini entered in 1970.

He began his career as a billboard painter for Landau Outdoor Advertising in Philadelphia, where attention to detail, craftsmanship, and hard work weren’t just valued—they were required. Every billboard had to be completed by hand, often high above busy roadways, and every stroke mattered.

Those early years gave him more than technical skills. They gave him a firsthand understanding of every part of the business. From construction and maintenance to location, visibility, and what makes outdoor advertising effective.

In 1977, Dominick founded Keystone Outdoor Advertising Company, Inc.

Like many entrepreneurs, he started with a simple goal: build something of his own.

His first billboard lease at I-676 and Callowhill Street in Philadelphia was followed by the construction of Keystone’s first monopole along the Walt Whitman Bridge. Those projects laid the foundation for what would become one of the largest independent outdoor advertising companies in the Philadelphia region.

Over the decades, the industry changed dramatically.

Hand-painted billboards gave way to vinyl production. Digital design replaced drafting tables. Static displays evolved into high-resolution digital billboards capable of delivering multiple messages every minute.

Through each change, Keystone evolved alongside the industry while remaining focused on the fundamentals: premium locations, dependable service, and long-term relationships with clients.

Today, Keystone’s inventory stretches throughout Pennsylvania and New Jersey, serving local businesses, regional brands, national advertisers, and agencies. While technology has transformed how outdoor advertising is delivered, the company’s approach has remained remarkably consistent: treat people fairly, deliver on commitments, and continue investing in the future.

If you ask Dominick about his career, he’s more likely to talk about the people he’s worked with than the milestones he’s achieved.

That’s probably why Keystone has remained independent for nearly five decades.

The company has never been just about billboards. It’s about building lasting relationships with clients, property owners, employees, and communities, and creating advertising that stands the test of time.

From paintbrushes to pixels, the tools have changed. The commitment behind them hasn’t.