SITUATION Progressive was a household name thanks to Flo, but within the independent trucking community, the brand had a serious perception problem. Truckers didn’t feel seen, understood, or respected by mainstream insurance providers—Progressive included. This was a loud, proud, and deeply skeptical audience, and we weren’t just fighting for their business—we were fighting for their trust. As Group Creative Director and Creative Strategist, I transformed what was a $100K ad hoc assignment into Trucker Territory—a brand-defining, multi-channel creative platform that deeply connected with truckers, outperformed KPIs, and exceeded sales goals. ​ TASK Reposition Progressive as a legitimate ally to truckers by building an emotional and cultural bridge between the brand and one of America’s most underserved professional communities. This campaign had to drive engagement, sentiment, and ultimately, policy growth—without feeling like a sell. ​ ACTION I hit the road. Literally. I spent weeks at truck stops across America, interviewing drivers, sleeping at truck stops, and learning the realities of the job—loneliness, pride, grit, freedom, and family. The insight was crystal clear: this wasn’t about coverage. It was about being seen. That led to the creation of Trucker Territory—a media-rich, emotionally intelligent platform that gave truckers a voice, a stage, and a space to connect. From heartfelt films to original music, comics, and podcasts, the campaign let truckers know Progressive wasn’t just talking at them. We were with them. Key actions and components: Docu-series storytelling: Award-winning branded documentaries featuring real truckers, Progressive’s highest-performing brand content to date Experiential activations: Large-scale tour stops at MATS and GATS, featuring live music (including American Idol talent) and immersive brand engagement Original music label: Wheelhouse Records launched with songs I wrote and co-produced, performed by Grammy-nominated artists Health & wellness content: Workout series with a trucker health advocate featured on GMA and ABC News Financial & mental wellness: Branded podcasts on PTSD, financial literacy, and the pressures of life on the road In-cab culture: Cooking videos, comics (Rig Riot), “Word on the Road” interviews—hyper-specific, authentic lifestyle content Facebook community: Built from zero into a thriving, high-trust audience with massive organic reach and engagement Support ecosystem: No stock content, no generic messaging—everything crafted for cultural specificity and emotional relevance ​ RESULT Trucker Territory transformed Progressive’s relationship with truckers—and drove real business results: Business Metrics +16% increase in qualified calls (500K+) +19% increase in quotes (99K) +9% increase in applications (39K) 6% YOY growth, outpacing the commercial insurance category Record number of active policies Social Impact 10M+ video views 65M+ total impressions 1.3M engagements, 204K link clicks, 52K shares 19K comments—organic, unprompted, often heartfelt Streaming concert watched by 225K+ CRM opt-in list grew from 0 to 45K in just 6 months—with zero paid push ​ REFLECTION Trucker Territory wasn’t just about shifting perception. It was about giving voice to a community that had long been overlooked—and building a brand platform on respect, not assumptions. It worked. We didn’t just create content—we created connection. So much so that years later, GEICO called and asked me to build something similar for them. When you lead with empathy and listen with intent, even the loudest critics can become your most loyal fans.