Filippo di Trapani
Staff Product Designer @Automattic
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WORK HISTORY
Staff Product Designer @Automattic
Ottawa, ON, CA
Designed and scaled AI-assisted support, improving resolution rates and reducing human escalation by 20%.• Led end-to-end product design for systems impacting millions of customers, from early concept through launch.• Built and optimized subscription, billing, migration, and checkout systems to increase revenue and reduce support interactions.• Drove data-informed product decisions through experimentation, research, and customer feedback.• Balanced complex business constraints with a high bar for craft across critical monetization surfaces.
EDUCATION
Algonquin College of Applied Arts and Technology
Design Foundations, Design Foundations
Algonquin College of Applied Arts and Technology
Graphic Design, Graphic Design
Algonquin College of Applied Arts and Technology
Interactive Multimedia, Web, Development, Flash Actionscript, HTML, CSS, JavaScript, PHP, Web Design, Interaction Design
SKILLS
ABOUT FILIPPO DI TRAPANI
Product design leader focused on building and scaling complex systems that drive revenue and reduce operational friction. I’ve led monetization, checkout, migration, and subscription platforms at WordPress.com, designed AI-assisted support experiences that reduced human escalation by 20%, and driven multiple 0→1 initiatives from early ambiguity through launch.I specialize in design systems at scale, cross-functional execution, and turning messy problem spaces into clear product strategy—while operationalizing the consistent delivery of high-craft, high-quality experiences.Selected Highlights• Built and scaled billing, checkout, migration, and subscription systems at WordPress.com, increasing revenue and reducing support load• Designed AI-assisted support experiences, improving resolution rates and reducing human escalation by 20%• Led multiple 0→1 product initiatives from research and prototyping through launch in highly ambiguous environments• Led and evolved design systems used by hundreds of thousands of users, improving quality, speed, and consistency• Drove cross-functional initiatives contributing millions in revenue across multiple companies
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