Shai Wininger is the Co-Founder and Co-CEO of Lemonade, Inc., a tech-driven insurance company that has changed how people think about insurance. Born in 1976, Shai studied Computer Science and has a strong tech background, having previously founded Fiverr, a...

Shai Wininger is the Co-Founder and Co-CEO of Lemonade, Inc., a tech-driven insurance company that has changed how people think about insurance. Born in 1976, Shai studied Computer Science and has a strong tech background, having previously founded Fiverr, a popular freelance services platform. He held various key roles at Lemonade since its launch in 2015, where his expertise in technology has played a significant role in shaping the company. In 2021, he transitioned to Co-CEO alongside Daniel Schreiber, but as of January 2024, he returned to the position of President. Shai's management style reflects a blend of tech savvy and innovative thinking, focusing on using artificial intelligence to disrupt the insurance sector. In various years, his compensation has included sizable stock options, reflecting his commitment and belief in the company’s future growth, as they aim for better customer experiences and deeper engagement in the market.

Quick Links

1. Rivals

2. Holdings

3. Insider Trading

4. Compensation History

5. Other Lemonade CEOs

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Shai Wininger

Founder and Ex-CEO of Lemonade

Education

Not specified

Field of Expertise

Technology & Engineering - Technology

Sector of Economy

Financial Services

Born

January 1, 1975 - 50 years ago

CEO of Lemonade for

2 years 5 months (Jul 2021 - Jan 2024)

Previous Experience

Founder and CTO of Fiverr Ltd.

Rivals

Competitors/colleagues of Shai Wininger

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Dave Girouard

Founder and CEO of Upstart Holdings, Inc.

2021 Compensation

Stock

$8.06M

Salary

$455.00K

Bonus

$0.00

Other

$0.00

Total Holdings

$401.64M

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Thomas J. Wilson

CEO of Allstate

2023 Compensation

Stock

$7.88M

Salary

$1.39M

Bonus

$0.00

Other

$156.28K

Total Holdings

$223.81M

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Matthew E. Winter

CEO of Allstate

2023 Compensation

Stock

$12.87M

Salary

$1.39M

Bonus

$2.08M

Other

$0.00

Total Holdings

$31.99M

P

Susan Patricia (Tricia) Griffith

CEO of Progressive

2023 Compensation

Stock

$46.83M

Salary

$994.23K

Bonus

$4.42M

Other

$217.95K

Total Holdings

$162.74M

A

Don Civgin

CEO of Allstate

2023 Compensation

Stock

$0.00

Salary

$1.39M

Bonus

$2.08M

Other

$0.00

Total Holdings

$21.29M

Holdings

See how much did Shai Wininger make over time.

Shai Wininger’s stock holdings have fluctuated greatly over the years. At one point in early 2021, his holdings were valued at around $2.31 billion after the company's initial surge, showcasing a peak of wealth tied to the company's growth. However,...

Shai Wininger’s stock holdings have fluctuated greatly over the years. At one point in early 2021, his holdings were valued at around $2.31 billion after the company's initial surge, showcasing a peak of wealth tied to the company's growth. However, by late 2022, this value decreased to approximately $519 million, indicating significant volatility in market valuation. As of early 2023, his total holdings had further reduced to about $232 million, highlighting the challenges in the market. Despite these fluctuations, Shai's ownership stake remains significant, demonstrating his long-term investment in Lemonade.

Mar 18, 2025

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shares

LMND @ $33.95

Total Stock Sold

$64.10M

LMND

$64.10M

536,500 LMND shares

What if they kept their stock?

If Shai Wininger didn't sell their stock, today they would have:
Extra LMND536,500 shares worth $37.24M.
This is -41.91% and $26.86M less than what they got when they sold the stock.

Insider Trading

See recent insider trades of Shai Wininger.

LMND

9,327 shares

LMND

Feb 2, 2024

Received

LMND

$3.27M

LMND at $126.92/share

Dec 24, 2020

Sale

LMND

$47.94M

LMND at $123.10/share

Dec 21, 2020

Sale

LMND

$928.39K

LMND at $102.01/share

Dec 17, 2020

Sale

LMND

$11.70M

LMND at $105.08/share

Dec 10, 2020

Sale

LMND

$90.17K

LMND at $99.52/share

Dec 7, 2020

Sale

Compensation History

See how much did Shai Wininger make over time.

In 2022, Shai Wininger's total compensation was approximately $534,313, which included a base salary of $375,225. While he did not receive annual bonuses, he was awarded 500,000 stock options meant to vest over four years, showing the company's focus on long-term performance linked to his leadership. His compensation reflects a growing trend in tech companies that tie executive pay to equity grants, emphasizing a model where success is aligned with shareholder interests. The company's approach aims to motivate executives to excel in their roles by ensuring that they have a vested interest in the performance of the company.

Year

2022

Total Compensation

$534.31K

Salary

$375.23K

Board Justification

The compensation philosophy is designed to attract, motivate, and reward leaders who create an inclusive and diverse environment and have the skills and experience necessary to execute the strategic plan to maximize stockholder value.

Bonus

$0.00

Board Justification

No annual cash incentive compensation was provided to NEOs in 2022.

Other

$159.09K

Board Justification

Includes contributions to pension plans, car allowance, and other benefits.

Restricted Stock

$0.00(0 N/A)

Board Justification

No stock awards were vested in 2022 as per the provided information.

Performance Metrics

Compensation is aligned with corporate and individual performance, rewarding superior performance and providing consequences for underperformance.

Other Lemonade CEOs

Here are other CEOs of Lemonade

Daniel Schreiber

Founder and Ex-CEO of Lemonade

June 2015 - July 2021

Daniel Schreiber

Founder and CEO of Lemonade

January 2024 - Present