Filippo Di Trapani is a Senior Product Designer in Ottawa with 11 years of experience designing and scaling complex monetization systems and product ecosystems for high-impact platforms. He has led end-to-end initiatives at Automattic and Shopify, driving measurable revenue gains through subscription, billing, onboarding and checkout optimizations while managing and mentoring design teams. Comfortable in 0–1 ambiguity and large-scale product operations, he blends rigorous user research, A/B testing and in-product feedback loops to turn insights into polished, revenue-driving experiences. A hands-on former front-end contributor to WordPress.com (wp-calypso), he brings practical UI engineering sensibilities to design solutions and design-system migrations. Beyond product metrics, he’s built internal tools and processes that improve cross-functional decision making and long-term team effectiveness.
Contributions:239 reviews, 251 commits, 579 PRs in 3 years 10 months
Contributions summary:Filippo primarily contributed to the front-end development of the WordPress.com platform, focusing on user interface enhancements. They fixed text color issues within the site preview component and updated hover effects. Additionally, they added affordances to the checklist component and added a graphic to the stats banner. Furthermore, the user made changes to the coupon and payment systems.
Contributions:47 commits, 10 PRs, 225 pushes in 3 years 5 months
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Filippo Di Trapani - Senior Product Designer at Automattic