Every roofing journey starts somewhere—and for Brittany Cherup, owner of Pit Crew Roofing®, it all began with a Rand McNally map book and a tape measure. Long before drones and digital tools, Brittany was mapping routes and measuring roofs by hand—laying the groundwork for a career defined by grit, precision, and heart.
Navigating with Paper and Purpose
Growing up between small-town Indiana and the bustling streets of Cincinnati, Brittany’s first role in roofing came at age 14: navigator. Using nothing but a paper map and raw instinct, she guided design consultants from home to home. GPS? Not a chance. Her early exposure to the field wasn’t glamorous—but it was foundational.
Learning the Tape Measure Tango
Brittany quickly moved from the passenger seat to the rooftop. Her job? Holding the “not-so-smart end” of the measuring tape while seasoned pros read and recorded dimensions. She helped chart out each roof with precision, building a unique, hands-on skill set that many young roofers today wouldn’t dream of trying.
Old-School Ingenuity Meets Real-World Speed
Forget tech shortcuts—Brittany mastered roof measuring with just a tennis ball, a fishing lure, and a tape measure. Toss the ball down to the gutter, extend the tape, and boom: measurements in minutes. It’s a method born from experience and efficiency that often outpaces modern tools.
A Skill Set That Sets the Pace
While younger contractors rely on software, Brittany’s years in the field taught her to estimate and diagram roofs the old-school way—faster and with less margin for error. Her foundation in analog methods shaped her into the roofing powerhouse she is today.
The Finish Line Is Just the Beginning
Today, Brittany leads Pit Crew Roofing® with the same energy she brought to those early jobs—only now she’s calling the shots. Ready to take your roof on a victory lap? Call us for a free estimate and experience expert service, start to finish.