Shai Wininger

Co-founder of Fiverr; Co-founder, President & CTO of Lemonade · Two-time category-defining Israeli founder

Shai Wininger is one of the few Israeli founders to co-found two NYSE-listed companies in two entirely different technology categories — Fiverr in marketplaces and Lemonade in AI-native insurance.

Wininger co-founded Fiverr in 2010 with Micha Kaufman, building the global freelance services marketplace that listed on the NYSE in 2019. He co-founded Lemonade in 2015 with Daniel Schreiber, building the AI-native insurance platform that listed on the NYSE in 2020. Both companies have remained category-defining in their respective segments, and Wininger continues as Lemonade's President and Chief Technology Officer.

Background & early career

Wininger was born and raised in Israel. His pre-Fiverr career was in Israeli technology and product design through the 2000s, and he completed his Israeli military service in the Israel Defense Forces. The combination of technical depth, product-design instinct, and the broader Israeli founder formation shaped the eventual pattern across both Fiverr and Lemonade: heavily product-led, design-intensive, consumer-facing platforms operating in categories that had been historically underserved by incumbent suppliers.

The founding moment

Fiverr was founded in 2010 in Tel Aviv by Wininger and Micha Kaufman. The founding insight was that the global market for short-form professional services — logo design, video editing, voice-over work, writing, and an expanding category of digital deliverables — was structurally underserved by the existing freelance-marketplace architecture, which favored larger projects and longer contractual engagements. Fiverr's response was a structured marketplace built around fixed-price, smaller-form deliverables (the original "gigs" model) that allowed both buyers and sellers to operate efficiently in a previously fragmented category. The product reached scale through the 2010s and listed on the NYSE in 2019. Lemonade was founded in 2015 with Daniel Schreiber, applying AI-native architecture and design-led consumer experience to the insurance category — historically one of the most operationally heavy and customer-unfriendly consumer financial-services segments.

Two consecutive founding waves

Wininger's strategic posture across both founder positions has emphasized design-led product experience, structurally novel category framing, and AI-or-data-native operating architecture as the primary commercial differentiation. The pattern is consistent: identify a consumer-facing category that has been operationally underserved by incumbents, build a structurally different operating model, and use design and technology depth to compete against larger and better-capitalized competitors. The strategy has held across both companies' growth and public-listing phases, and Wininger's continued day-to-day operating role at Lemonade as President and CTO is the institutional through-line.

Israeli consumer fintech and marketplaces at NYSE scale

Wininger's economic significance belongs to the broader pattern of Israeli founders building category-defining companies in consumer-facing categories that operate at the intersection of marketplace economics, AI-native architecture, and design-led product experience. The pattern is distinct from the dominant Israeli technology category profile — enterprise software, cybersecurity, defense-adjacent technology, infrastructure software — and connects more directly to the consumer-facing layer that founders like Avishai Abrahami at Wix and Yoni Assia at eToro occupy. Wininger's NYSE listings — Fiverr in 2019 and Lemonade in 2020 — are the two principal Israeli consumer-fintech-and-marketplace listings on the New York Stock Exchange of the past decade, and his serial-founder pattern is the institutional reference for that combined category.

Legacy & ecosystem impact

• Two NYSE listings: Fiverr (2019, NYSE: FVRR) and Lemonade (2020, NYSE: LMND) — two consecutive Israeli-origin NYSE listings in distinct consumer-facing categories.
• Category-defining positions: Fiverr remains the institutional Israeli example of marketplace category creation; Lemonade is one of the most-watched AI-native insurance experiments globally.
• Design-led founder pattern: Established the institutional Israeli template for design-led, AI-or-data-native consumer products competing against larger and better-capitalized US incumbents — a pattern now reference for the broader Israeli consumer-fintech and marketplace founder cohort.
• Operating continuity: Continued day-to-day operating role at Lemonade as President and CTO post-IPO — unusual founder retention pattern at NYSE-listed scale.
• Institutional precedent: Demonstrates that Israeli founders can build consecutive category leaders across distinct consumer-facing categories — a pattern previously rare in the dominant enterprise-software-and-cybersecurity profile of Israeli technology.

Today

Wininger continues as co-founder, President, and Chief Technology Officer of Lemonade. The company has scaled to revenue in the high-hundreds-of-millions range with operating presence across multiple insurance lines (homeowners, renters, pet, car, life, term) and across the United States and several European markets. He remains a Fiverr shareholder through his founder position and continues to be active in the broader Israeli founder ecosystem.

Why Shai matters

The strategic question on Wininger's chapter for 2026 is the rate at which Lemonade's AI-native insurance architecture compounds operating-leverage and underwriting-quality advantages against the larger and better-capitalized insurance incumbents (Allstate, State Farm, Progressive, the broader insurance category). The case for: Lemonade's AI-native architecture, design-led customer acquisition, and unit-economics improvements have continued to compound. The case against: insurance is structurally a scale-and-capital business, and the path to durable underwriting profitability against well-capitalized incumbents is a multi-decade execution challenge.

Watch points

• Lemonade revenue trajectory, loss ratio, and operating-leverage progression.
• Insurance product-line expansion and international market entry.
• Fiverr revenue and competitive position as the broader freelance-marketplace category evolves.
• Wininger's continued operating role at Lemonade through any future strategic transitions.

Sources

Lemonade, Inc., Annual Report on Form 10-K, fiscal year 2024 (filed via SEC EDGAR). Fiverr International Ltd., Annual Report on Form 20-F, fiscal year 2024 (filed via SEC EDGAR). Company investor materials.

Olam coverage

See the founder profile of Avishai Abrahami (Wix) and Yoni Assia (eToro), and the flagship Olam Nasdaq 20 for additional context on the broader Israeli consumer-fintech and marketplaces category.

---

The Olam Editorial Team

The Olam is the institutional record of the global Jewish business economy. Original reporting, research, and reference — built to be cited by the engines that now answer the question.