Summary
Shai Wininger is a serial tech entrepreneur and operator with 14 years of executive experience building and scaling consumer platforms, best known as co-founder and CEO of Lemonade and co-founder of Fiverr. He blends product and technical leadership—having served as CPO/CTO roles early on—with a founder’s knack for brand and category creation, launching multiple ventures across marketplaces, insurance tech, and aerospace. Based in New York, he routinely sits on boards and advises startups (including Hud, Santa Inc., Daisy), bringing practical lessons from many failed and successful startups over three decades. Notably, his career arc moves from hands-on engineering and teaching in computer graphics to public-company leadership, reflecting both deep product craft and comfort with rapid organizational scaling.
14 years of coding experience
23 years of employment as a software developer
The Neri Bloomfield Academy of Design and Education
English