Bobby Gillespie
Expert Brand Strategy & Creative Leader for High-Growth Companies
I believe every brand has an unrealized potential waiting to be shaped, expressed, and scaled. I work with CEOs and leadership teams that want to bring that potential to life with intention and confidence.
After years inside agencies building brands of every shape and size, I now partner directly with companies as an embedded creative and brand strategy lead. I help leaders create clarity, define strong positioning, and build innovative brand systems that support growth without chaos.
Your vision becomes the north star.
Your brand becomes the operating system that organizes everything else.
My work focuses on three things:
1. Sharpening your brand positioning so your value is unmistakable
2. Leading creative direction that reflects the strength of your company
3. Establishing systems that keep your brand consistent at scale
When we work together, you gain a partner who understands how to build, manage, and evolve a brand that performs in real time. You also get a collaborator who thinks with you, challenges you, and helps you see the opportunities you may be too deep in the work to notice.
Your best brand is ahead of you, not behind you. Let’s go build it.
From the grey matter
Bobby G: A Curious, Creative, and Relentlessly Driven Mind
Bobby Gillespie, or just Bobby to his friends, is not a yes man. He is an idea guy.
From the beginning, Bobby was fueled by creativity and curiosity. As a spirited middle child, his parents noticed his hunger for learning and expression early on and enrolled him in every art class they could find. By the time he was four, his Pac-Man drawings outshined his older sister’s, and he never stopped improving. But drawing was just one outlet. His real obsession was learning by doing. That led to plenty of mischief as a kid, but over time, his curiosity evolved into a more focused passion for art, science, and history.
Misguided by poor academic advising in high school, Bobby entered La Salle University in Philadelphia as a science major, studying biology before switching to earth sciences. He loved the structure of the scientific method, a framework he still applies today, but science could not hold his passion. At the time, the idea of a creative career felt out of reach. As Bobby put it, “I didn’t want to be a starving artist. When I thought of a creative career, I only saw fine arts.”
The Epiphany
Everything changed during his junior year of college. Struggling to balance a heavy academic load with an active social life, Bobby joined some friends on a spring break road trip to the Gulf Coast of Florida. Along the way, they stopped in Savannah to visit a friend’s brother at SCAD, the Savannah College of Art and Design. The dorms were in a converted motel, and the moment Bobby arrived, he was stunned.
“I remember thinking, what the hell is everyone doing here?” he said. “Then I asked, what are you going to school for? My jaw dropped.” He quickly learned these students were studying illustration, animation, graphic design, photography, and more. That visit changed everything.
When he returned to La Salle, Bobby went straight to the dean’s office and began the process of transferring to art school.
Reigniting the Creative Spark
Over the next few years, Bobby immersed himself in creative education. He took fine arts courses at the Pennsylvania College of Art and Design, earned a degree in Animation from the Art Institute of Philadelphia, and completed a degree in Digital Arts and Multimedia Design from La Salle. By the time he re-entered the workforce, he had landed his first industry job as a director at a dot com startup, and he was all in.
Bobby then moved into the beer industry, working as a senior designer and art director. He challenged the traditional way of doing things by forging collaborative relationships between customers, sales teams, marketers, and brewers, rather than settling for transactional ones. After gaining experience at a design firm, he relocated to Baltimore to work in the consumer packaged goods space, where he created full brand systems for products on shelves and online.
Never one to settle, Bobby went back to school, this time for a master’s degree at the University of Baltimore. His goal was to leap ahead a few rungs on the career ladder. He graduated with nearly a 4.0 GPA, earning recognition both in school and in the local creative community.
Building a Reputation and a Company
After graduate school, Bobby began freelancing as a designer and art director, but his sights were set on becoming a creative director at an agency. Within two years, and after a few disappointing opportunities, he achieved that goal. He became the first creative director at a growing ecommerce and marketing agency.
In that role, Bobby shaped not just the creative output, but also how the work got done. He led successful projects worth hundreds of thousands of dollars, aligning brand strategy and creative execution with marketing goals. His legacy there was a seamless integration of design, technology, and marketing.
Propr and the Entrepreneurial Pivot
After almost two and a half years at the digital agency, Bobby began to seek something more. That drive led him to found Propr, a strategy-first branding agency focused on delivering complete brand systems, especially enterprise websites. Propr has worked with clients across consumer products, direct to consumer, business to business, and business to consumer industries, consistently delivering strong results and profit margins of 40 to 50 percent in an industry where single digits are the norm. He built a lean and powerful team to bring the work to life.
Along the way, Bobby completed the Goldman Sachs 10,000 Small Businesses program and was an Elite 10 at the CCBC Entrepreneur Accelerator, which helped round out his understanding of the intricacies of how a business operates, and align with his extensive experiences with brand and marketing. He also published his first book, Build Your Brand Like You Give A Shit, a gutsy manifesto on what it takes to build a successful brand without losing your soul.
Still, Bobby felt the pull toward deeper and more meaningful work. Ten years after founding Propr, he returned to a solo path, this time focused on doing the most fulfilling and impactful work of his career—helping CEOs and executives solve complex business problems through creativity, curiosity, and strategic experimentation.