Episode Summary
Karolyn Raphael didn’t set out to run an agency—she was chasing a career in performance. But when life redirected her from the stage to the newsroom, she discovered her knack for storytelling could shine even brighter in PR. Fast forward, and she’s now the owner of Winger Marketing, a Chicago-based agency she acquired from its founders and reinvented to meet the demands of a rapidly digitizing world.
In this episode, Karolyn discusses:
- How she transitioned from a young theater professional to leading a B2B marketing agency with global reach.
- The decision to transform Winger Marketing from traditional PR to full-service digital.
- How continuous learning and high-touch service have fueled her agency’s quadruple growth.
Agency Info
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Company: Winger Marketing
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Guest: Karolyn Raphael
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Year Started: 1986
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Employees: 1-10
Most entrepreneurs believe no one can do it as well as they can. That’s the trap.
Karolyn Raphael
Key Takeaways
Reinvention Begins with Self-Awareness
Karolyn candidly shares how she realized PR was her stage and storytelling her superpower. Recognizing this shift allowed her to embrace a new path without regret. Her transition was built not just on passion, but on opportunity—from a pivotal internship at Indiana University to taking over Winger Marketing in 2006.
From Employee to Owner: The Power of Saying Yes
When the original owners were ready to retire, Karolyn had just returned from maternity leave. Despite personal and financial uncertainty, she and her husband bought the firm. With no formal roadmap, Karolyn had to modernize Winger from paper ledgers and a shared dial-up connection to digital systems, laying the groundwork for a full-service agency.
Digital Evolution Is Non-Negotiable
Shrinking media landscapes and the rise of social made it clear PR alone wasn’t enough. Karolyn pivoted the agency to offer holistic digital marketing, blending thought leadership, SEO, social, and content with her roots in earned media.
Value-Based Pricing Wins Over Price Cutting
Her journey underscores the danger of competing on price. She encourages agency owners to align fees with real value delivered and to avoid the trap of “doing more for less.”
Never Stop Learning
At Winger, every employee has a budget for ongoing education. Weekly learning sessions keep the team sharp, especially in an industry where tech shifts rapidly. Karolyn’s team treats AI like a teammate—even learning that being polite to ChatGPT yields better responses.
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