Shai Wininger

According to Lemonade’s biography, Wininger held a senior management role at Trimus, a virtual-reality web-browser business, from 1999 to 2003.⁠[1]

From 2002 to 2007, he was a resident faculty member in computer graphics at the Neri Bloomfield Academy of Design and Education in Haifa, Israel.⁠[2]

He held a senior management role at Handsmart Software from 2003 to 2005. Its platform supported licensing for content-driven mobile applications.⁠[1]

From 2005 to 2010, he held a senior management position at Mobideo Aerospace, an industrial analytics and control platform.⁠[1]

Wininger and Micha Kaufman cofounded Fiverr in 2009, organizing freelance services as purchasable online offerings. As CTO, Wininger oversaw engineering, design and product. His later account described growth after the early-2010 launch, distinguishing the venture’s start from its public rollout.⁠[3][1][4]

On February 2, 2013, Wininger described Fiverr’s use of Ruby on RailsRuby on RailsRuby on Rails (often shortened to Rails) is an open-source, full-stack web application framework written in the Ruby programming language that builds database-backed web applications following the model–view–controller (MVC) pattern. Created by David Heinemeier Hansson and first publicly released in 2004, it is known for design principles such as “convention over configuration,” and companies including GitHub and Shopify use it in production.Open the full entry and database scaling. He emphasized early architectural planning and acknowledged human errors and infrastructure failures. On June 5, he introduced Fiverr V2 after nearly a year of development; access was still being rolled out.⁠[4][5]

Wininger and Daniel SchreiberDaniel SchreiberDaniel Schreiber is Lemonade’s cofounder, CEO and Chairman. His earlier career spanned law, software and consumer electronics, including the presidency of Powermat. He also founded and chairs the MOSAIC AI Policy Institute, addressing algorithmic fairness, employment and income distribution.Open the full entry cofounded Lemonade in June 2015, applying software and interaction design to insurance. The company began selling policies in New York on September 21, 2016. Wininger held successive technology, operations and corporate-governance roles.⁠[2][6]

In February 2016, Wininger announced Dan Ariely’s appointment as Lemonade’s Chief Behavioral Officer. He said Ariely’s research influenced his thinking about user experience and the team’s attempt to encourage honest reporting through design. This expressed a product objective, not independently demonstrated fraud-reduction results.⁠[7]

Writing shortly after Lemonade’s launch, Wininger explained that AI Jim determined whether a claim could be handled automatically or should go to a person. He linked behavioral research to conversational design while stressing that AI did not mean every claim would be paid automatically.⁠[8]

Lemonade listed on the New York Stock Exchange on July 2, 2020. Wininger remained in leadership as the business expanded its products and geographic reach.⁠[9][1]

Wininger became Lemonade’s co-CEO alongside Schreiber in July 2021, a start date explicitly recorded in the company’s 2023 proxy statement.⁠[10]

When Lemonade Car launched in November 2021, Wininger described building teams for roadside assistance, repairs and claims. The product combined driving data with digital claims processes and initially served Illinois.⁠[11]

During the co-CEO period, Lemonade completed its Metromile acquisition on July 28, 2022, adding automotive data and staff for mileage-based insurance. The company presented the transaction as a way to accelerate its car-insurance business.⁠[12]

On December 18, 2023, the board approved a return to the founders’ previous arrangement, effective January 1, 2024: Schreiber as CEO and Wininger as President. The filing said they preferred its clearer responsibilities to the co-CEO structure. Both remained directors.⁠[13]

On October 8, 2026, President Wininger introduced support for Tesla Hardware 3: a 30% discount on FSD (Supervised) v14 Lite miles in Arizona, Colorado and Tennessee. The release specified 50% for Hardware 4 with FSD v14.2 or later. Data sharing requires customer permission, and FSD still requires active driver supervision.⁠[14]

In The Rise of the Autonomous Organization, Wininger advocated software for repetitive organizational work and described Lemonade’s Cooper tool for engineering, testing and deployment. He also warned that efficiency could erode an organization’s human character and opposed AI deciding whom to hire or fire.⁠[15]

Wininger also worked with Roee Adler and May Walter to establish Hud, as Adler’s public introduction records. Hud provides software runtime context to engineers and AI coding tools to identify problems and understand code behavior.⁠[16][17]

Lemonade’s claims automation faced privacy scrutiny during Wininger’s leadership. The company denied using emotion recognition for automatic claim denials. The Clarke biometric-video case settled for $4 million in 2022 without an admission of wrongdoing. That corporate dispute does not establish personal misconduct by Wininger.⁠[18][19][20]