Preface

I like impossible goals, ambitious strategies and big ideas that make everyone lean in, tune in and get excited. Progressive Small Biz Battles was one of those activations. We turned boring, cookie-cutter content into an exciting, celebrity-led program that influenced tens of thousands of small-business entrepreneurs and became Progressive Commercial's high-performing content on its digital hub.

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The Challenge: Redefining Insurance Content with Educatainment

Yada, yada, yada. Superficial small business advice pollutes the internet. The challenge was to execute a radical redefinition of insurance content marketing: moving the brand beyond self-serving fluff and generic advice toward authentic, actionable learning (edutainment). The goal was to create content so compelling and valuable that small business owners would choose to engage, proving Progressive was a true "Partner in Progress."

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The Action: Directing a Radically Different Content Model

As the Creative Director for Content Strategy and Production, my role was to conceive and execute a new content hybrid that was both commercially entertaining and deeply educational.

• Conceptual Redefinition: I conceived and directed Small Biz Battles—a high-energy, docu-style reality content series that served as the vehicle for this edutainment strategy. The format was designed to be culturally relevant and actionable, not promotional.

• Hands-On Production & Talent Integration: I directed the seamless blend of professional production (filming food trucks on Venice Beach) with celebrity presence, integrating film icon Danny Trejo to authenticate the street-level hustle while managing the creative strategy to ensure the entertainment factor was balanced with practical business truth.

• Actionable Content Strategy: Crucially, I designed the campaign to go beyond video, directing the creation of a seamless content hub filled with downloadable startup kits, business toolkits, and insurance explainers. This ensured the campaign's high-impact entertainment instantly converted into tangible, actionable learning for the small business owner.

• 360-Degree Execution: I oversaw the strategic deployment of the entire mix—from the video series to the CRM nurture streams and experiential activations—maintaining conceptual rigor across every educational and entertainment touchpoint.

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The ROI: Content Value Drives High-Quality Applications

The successful execution of this radically different content model drove massive engagement and proved that valuable edutainment is the highest-performing content strategy in the category. While the brand did not share social media or sales data, they did provide these notes:

• Content Performance: Delivered Progressive’s highest-performing small business content of the year, driving positive brand sentiment through authentic, relevant storytelling.

• Business Impact: Generated a significant lift in qualified small business insurance applications and thousands of downloads of toolkits and educational content.

• Engagement: Achieved massive engagement with the video series and microsite, proving the content's value and credibility, which is essential for selling a high-trust product like insurance.