Lemonade co-CEO Shai Wininger leaves post

  • After about two and a half years in the position
  • Elimination of dual Chief Executive Officer role
  • Daniel Schreiber becomes sole Chief Executive Officer
  • Wininger will remain as President at Lemonade

(exechange) — New York, December 21, 2023 — Shai Wininger, co-chief executive of Lemonade, leaves his position. As announced by Lemonade Inc. in a regulatory filing published on Thursday, December 21, 2023, Shai Wininger leaves his post as co-chief executive officer at the digital insurance company, after about two and a half years in the role, effective January 1, 2024.

Generally speaking, it raises questions when a co-CEO leaves his post at short notice and after a short tenure.

Lemonade eliminates the dual Chief Executive Officer role. Daniel Schreiber will be sole Chief Executive Officer.


Lemonade did not give an explicit reason for Shai Wininger’s departure from the co-CEO post. Lemonade stated: “After two and a half years as Co-CEOs, the Company’s current Co-Executive Officers, Shai Wininger and Daniel Schreiber, prefer to return to their previously held positions as the Company’s President and the Company’s Chief Executive Officer, respectively, because they believe that the clarity this structure provides outweighs the benefits of the Co-Chief Executive Officer structure. After considering their preference for this leadership structure, on December 18, 2023, the Board of Directors of Lemonade, Inc. (the“Company”) duly appointed Shai Wininger as the Company’s President and Daniel Schreiber as the Company’s Chief Executive Officer, effective January 1, 2024 (the “Effective Date”).”

Share price decline since July 2021

The announcement follows a decline in Lemonade Inc.’s share price of 85% since July 2021. July 2021 is the month in which Wininger’s tenure as co-CEO began.

In the position of CEO since 2021

Shai Wininger became CEO of the Company in 2021.

Shai Wininger has served in various roles, including as the Company’s Co-Founder, Secretary, Treasurer, and Chief Technology Officer, since the Company’s founding in June 2015.

Wininger has served as the Company’s Co-Chief Executive Officer since July 2021, and is a member of the Company’s board of directors.

Prior to co-founding Lemonade in 2015, Wininger founded Fiverr Ltd. in 2009, and as the Chief Technology Officer, managed the engineering, design, and product departments. Prior to 2010,

Wininger served in senior management capacities for companies including: from 2005 to 2010, Mobideo Aerospace, an industrial grade analytics and control platform; from 2003 to 2005, Handsmart Software, a mobile licensing platform for content driven, mobile apps; and from 1999 to 2003, Trimus Inc., a virtual reality web browser.

Wininger also served as a resident faculty member of Computer Graphics at The Neri Bloomfield Academy of Design and Education from 2002 to 2007 in Haifa, Israel.

No statement by Shai Wininger

The announcement of his departure as co-CEO does not include a statement by Shai Wininger.

Push-out Score for Shai Wininger’s move determined

The Push-out Score indicates on a scale of 0 to 10 how likely it is that Shai Wininger was pushed out or felt pressure to leave his position.

exechange reached out to Lemonade and offered the company the opportunity to comment on the score.

Read the full story in the exechange report 52.2023 ($).