Shai Wininger – President & Co-Founder of Lemonade

Shai Wininger – President & Co-Founder of Lemonade

Shai Wininger is the President and Co-Founder of Lemonade, the technology-driven insurance company that uses artificial intelligence, automation, behavioral economics, and a digital-first customer experience to provide insurance products across the United States and Europe.

Wininger co-founded Lemonade with Daniel Schreiber in 2015, bringing a technology and product background to an industry traditionally dominated by legacy systems, brokers, paperwork, and complex customer processes.

Although Wininger is frequently described online as a CEO because he previously served as Lemonade's Co-Chief Executive Officer, he is not the company's current CEO. Lemonade's current governance materials identify Daniel Schreiber as CEO and Co-Founder, while Wininger serves as President and Co-Founder. Wininger became President on January 1, 2024.

Before Lemonade, Wininger founded Fiverr in 2009 and served as its Chief Technology Officer, overseeing engineering, design, and product. His experience building a global digital marketplace became an important part of his approach to creating Lemonade as a technology-native insurance company.

Today, Wininger is closely involved in Lemonade's technology, product, and growth strategy. In 2026, his work has included the company's expansion of car insurance, AI-powered insurance infrastructure, and new products such as Lemonade Autonomous Car, which uses data from autonomous driving systems to adjust insurance pricing.

Who Is Shai Wininger?

Shai Wininger is an Israeli technology entrepreneur best known as the co-founder of Lemonade and the founder of Fiverr.

His career has largely followed one theme: using software to redesign industries that historically depended on complicated processes and intermediaries.

At Fiverr, Wininger helped create a technology marketplace where buyers could connect with independent sellers offering digital services.

At Lemonade, he applied a similar technology-first philosophy to insurance.

Instead of treating insurance as primarily a financial product, Lemonade was designed from the beginning as a digital consumer experience. Customers could interact with the company through an app, while machine learning and automation were used throughout underwriting, claims, customer service, and other parts of the insurance process.

Wininger's career is therefore closely associated with two companies that attempted to use technology to reshape established business models.

Shai Wininger's Role at Lemonade

Wininger has held several leadership positions at Lemonade since the company's founding in June 2015.

According to Lemonade's 2025 annual report, he has served at different times as:

• Co-Founder

• Co-Chief Executive Officer

• Chief Technology Officer

• Secretary

• Treasurer

• President

• Director

He became President on January 1, 2024, and remains a member of Lemonade's board.

The current executive structure separates his role from that of Daniel Schreiber.

Schreiber is responsible for the CEO role, while Wininger serves as President and continues to contribute to Lemonade's technology, product, and strategic direction. Lemonade's official governance page confirms the current structure.

This distinction is important because older articles and biographies may still describe Wininger as Lemonade's co-CEO.

Early Career

Before founding Fiverr and Lemonade, Wininger worked across several technology companies.

Lemonade's SEC filings list senior management positions at:

• Mobideo Aerospace, where he worked from 2005 to 2010

• Handsmart Software, where he worked from 2003 to 2005

• Trimus Inc., where he worked from 1999 to 2003

His early career covered areas including software, mobile applications, industrial analytics, control systems, and web technology.

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

These experiences helped establish the technical foundation that later became central to his entrepreneurial career.

Founding Fiverr

In 2009, Wininger founded Fiverr, an online marketplace for digital services.

The original concept was simple: create an online marketplace where people could offer services to customers around the world.

Wininger became Fiverr's Chief Technology Officer and managed the company's engineering, design, and product departments.

The experience was particularly relevant to his later work at Lemonade.

Fiverr required technology to connect millions of users, automate transactions, manage trust, and create a simple interface for a complicated marketplace.

Insurance presented a different industry but a similar technological challenge: simplify a complicated process while maintaining the infrastructure required to operate at scale.

From Fiverr to Lemonade

Wininger's transition from Fiverr to Lemonade was not simply a move from one startup to another.

It represented a shift from transforming a marketplace to transforming an entire industry.

Insurance had existed for centuries, with established carriers, brokers, agents, paperwork, underwriting processes, and claims systems.

Wininger and Schreiber believed that technology could fundamentally change how insurance worked.

In Lemonade's founders' letter, the pair argued that technological changes were affecting virtually every part of insurance, from distribution and statistical tools to management, cost structures, customer experience, data, and technology infrastructure.

Their answer was to build an insurance company from scratch rather than attempting to modernize an existing insurer.

The Founding of Lemonade

Lemonade was founded in 2015 by Wininger and Schreiber.

The company's initial concept combined insurance with technology, behavioral economics, and social impact.

Rather than relying heavily on traditional insurance intermediaries, Lemonade built a digital experience in which customers could obtain policies and file claims through technology.

Artificial intelligence and machine learning became central to the company's operating model.

Lemonade also introduced a different approach to the relationship between premiums and claims through its Giveback program, under which unused premiums can be donated to causes selected by customers.

The founders described their goal as creating a new type of insurance company built around modern technology rather than attempting to retrofit legacy infrastructure.

Building an AI-Native Insurance Company

One of Wininger's most important contributions to Lemonade has been its technology architecture.

Lemonade describes itself as a technology-driven insurance company, with AI and machine learning integrated into its insurance operations.

The company says its full-stack insurance carriers replace traditional brokerage and bureaucracy with technology, aiming to reduce paperwork and provide faster customer experiences.

This approach is different from simply adding an AI chatbot to an existing insurance business.

The company's technology is integrated into areas such as:

• Customer acquisition

• Underwriting

• Pricing

• Claims

• Fraud detection

• Customer service

• Insurance operations

• Data analysis

Wininger's technical background made him particularly relevant to this strategy.

Lemonade's Expansion Beyond Renters Insurance

Lemonade originally became known for renters insurance.

The company subsequently expanded into several additional insurance categories.

Its current product portfolio includes:

• Renters insurance

• Homeowners insurance

• Car insurance

• Pet insurance

• Life insurance

The company operates in the United States and several European markets, including Germany, the Netherlands, France, and the United Kingdom.

This expansion has transformed Lemonade from a specialized renters-insurance startup into a broader consumer insurance platform.

Lemonade Reaches $1 Billion in In-Force Premium

A major milestone came in March 2025 when Lemonade announced that it had surpassed $1 billion in In-Force Premium (IFP).

The company said it reached the milestone approximately 8.5 years after selling its first policy and attributed its growth to technology, a broader product portfolio, geographic expansion, and its customer experience.

Wininger described the milestone as an important achievement while emphasizing the company's longer-term growth ambitions.

The milestone was also significant because Lemonade had expanded substantially beyond its original renters-insurance business by this point.

Lemonade's Growth in 2026

Lemonade entered 2026 with accelerating growth.

The company's second-quarter 2026 results showed $1.43 billion in In-Force Premium, representing approximately 32.4% year-over-year growth.

Revenue reached $294 million, up 79% year over year, while gross profit increased 76% to $113 million.

Lemonade also reported 3.31 million customers and $19 million in adjusted free cash flow for the quarter.

These results demonstrate how far Lemonade has moved from its original startup phase.

The company is now operating across multiple insurance categories while continuing to invest heavily in technology and geographic expansion.

Shai Wininger and Lemonade Car

Car insurance has become one of Lemonade's major growth opportunities.

The company has been expanding Lemonade Car into additional U.S. states while using its technology and data infrastructure to develop differentiated pricing.

In August 2026, Lemonade launched its car insurance product in Florida, one of the largest U.S. auto-insurance markets.

Wininger said the product was designed around digital-first customers and uses driving data to support pricing and discounts.

The Florida expansion brought Lemonade Car into states representing nearly 50% of the U.S. car-insurance market, according to the company.

For Wininger, the expansion of car insurance represents an important application of Lemonade's technology beyond its original products.

Autonomous Car Insurance

One of Wininger's most notable technology initiatives in 2026 has been Lemonade's work on insurance for autonomous vehicles.

In January 2026, Lemonade introduced Lemonade Autonomous Car, initially targeting Tesla vehicles using Full Self-Driving (Supervised).

The product uses driving data to differentiate autonomous driving from human-driven miles.

Lemonade announced that Tesla owners could receive approximately 50% lower pricing per mile for autonomous driving miles, reflecting the company's assessment of the lower risk associated with the technology.

In June 2026, Lemonade expanded the autonomous-car product to Indiana.

The company has continued expanding the offering to additional states.

This product demonstrates a key part of Wininger's technology philosophy: insurance pricing can change as the underlying technology and risk profile of the insured activity changes.

Using Data to Rethink Insurance Pricing

Traditional insurance relies heavily on historical data and established actuarial models.

Technology allows insurers to incorporate new sources of information.

Lemonade has increasingly focused on using real-time and behavioral data to improve underwriting and pricing.

The autonomous-car product is one example.

Instead of treating all miles driven by a customer as equivalent, Lemonade can distinguish between human-driven and autonomous-driving miles.

Wininger described the company's approach as using intelligent pricing models to translate safer driving technology into lower insurance prices.

This illustrates the broader opportunity that Lemonade sees in combining insurance expertise with technology infrastructure.

Wininger's Product and Technology Philosophy

Wininger's career has consistently focused on reducing friction.

At Fiverr, the challenge was making it easy for buyers and sellers to transact online.

At Lemonade, the challenge is making insurance easier to purchase, understand, price, and claim.

The common thread is the use of technology to simplify processes that traditionally required multiple steps and intermediaries.

His role has therefore extended beyond pure engineering.

At both companies, Wininger has worked across product, design, engineering, and business strategy.

That combination has shaped his approach to building consumer technology.

Lemonade's Founders' Philosophy

The original Lemonade founders' letter provides an unusually direct look at Wininger and Schreiber's philosophy.

They described the company as a long-term attempt to reinvent insurance rather than simply optimize an existing insurance business.

Several principles stand out.

Build From Scratch

The founders believed legacy insurance companies faced structural challenges because their technology and operating models had evolved over many decades.

Lemonade was designed without those legacy constraints.

Use Data, Not Just Intuition

The founders described themselves as risk takers rather than thrill seekers, emphasizing data-driven decisions while acknowledging that decisions often have to be made before complete information is available.

Think Long Term

The founders argued that insurance markets change slowly and that building a major insurance brand would require patience.

Combine Profit and Social Impact

Lemonade was established as a Public Benefit Corporation, reflecting the founders' view that financial performance and social impact do not necessarily have to be competing goals.

These principles remain visible in Lemonade's business model.

From CTO to President

Wininger's role at Lemonade has evolved considerably.

During the company's early years, his responsibilities were heavily focused on technology.

He served as CTO and was deeply involved in building the company's technology infrastructure.

He also served as co-CEO alongside Daniel Schreiber.

In January 2024, Wininger transitioned to the role of President, while Schreiber continued as CEO and Chairman.

The change allowed Wininger to focus on broader company responsibilities while maintaining his involvement in Lemonade's technology and product strategy.

Shai Wininger and Fiverr's Legacy

Wininger's work at Fiverr remains an important part of his entrepreneurial profile.

Fiverr became one of Israel's best-known technology companies and eventually went public on the New York Stock Exchange.

Wininger's role as founder and CTO gave him experience building a technology platform that could operate across borders and connect users globally.

That experience was valuable when Lemonade began expanding outside the United States.

Both businesses depend on digital distribution and technology-enabled customer experiences, even though their underlying industries are very different.

Lemonade's International Expansion

Lemonade has expanded beyond the United States into Europe.

The company currently offers insurance in the United States, Germany, the Netherlands, France, and the United Kingdom.

International expansion creates additional opportunities but also introduces different regulatory systems, insurance markets, customer behaviors, and pricing requirements.

For a technology-first insurer, the challenge is balancing a common platform with the need to adapt products to individual markets.

Wininger's experience scaling digital businesses internationally provides relevant experience for this expansion.

Challenges Facing Shai Wininger and Lemonade

Lemonade's growth strategy also creates several challenges.

Insurance Is a Capital-Intensive Business

Unlike many software companies, insurance requires significant capital and careful risk management.

Growth therefore has to be balanced with underwriting performance, reinsurance, and regulatory requirements.

Car Insurance Is More Complex

Lemonade's expansion into auto insurance significantly increases its addressable market but also introduces more complicated claims and risk models.

AI Must Produce Measurable Results

AI is central to Lemonade's identity, but the technology must ultimately improve pricing, claims, customer service, fraud detection, or operating efficiency.

International Regulation

Each insurance market has its own regulatory requirements.

Competition

Lemonade competes with established insurance companies as well as other technology-focused insurers.

Scaling Culture

The company has grown from a small startup into a publicly traded insurer with millions of customers.

Maintaining startup-level innovation while operating at this scale remains an ongoing organizational challenge.

Lemonade's Financial Direction

Lemonade's recent financial trajectory shows substantial improvement.

In Q2 2026, the company reported:

• $1.43 billion in In-Force Premium

• 32.4% year-over-year IFP growth

• $294 million in revenue

• 79% year-over-year revenue growth

• $113 million in gross profit

• 3.31 million customers

• $19 million in adjusted free cash flow

The company also said it expected its first positive adjusted EBITDA quarter in Q4 2026.

This combination of growth and improving profitability is an important part of Lemonade's current development.

The Role of Technology in Lemonade's Future

Wininger's technology background remains highly relevant to Lemonade's future.

The company is increasingly using AI and data across the insurance lifecycle.

Potential areas include:

• Automated underwriting

• Personalized pricing

• Claims automation

• Fraud detection

• Customer service

• Risk assessment

• Autonomous vehicle insurance

• Product development

The autonomous-car initiative provides a particularly clear example of how Lemonade's technology strategy could create entirely new insurance products.

As vehicles become increasingly autonomous, the nature of driving risk changes.

An insurer with a technology-first architecture can potentially adapt pricing models more quickly to those changes.

Shai Wininger's Leadership Legacy

Wininger's entrepreneurial legacy extends across two major technology companies.

At Fiverr, he helped establish a digital marketplace that connected buyers and sellers globally.

At Lemonade, he helped build an insurance company around software, AI, automation, and consumer experience from the beginning.

His career is particularly notable because he has remained deeply involved in the technical side of both businesses.

Rather than moving completely away from technology as his companies grew, Wininger continued to influence product and technology strategy.

That combination of engineering, product design, entrepreneurship, and business leadership has defined much of his career.

What Is Next for Shai Wininger?

Wininger's next phase at Lemonade is closely connected to the company's expansion into larger and more complex insurance markets.

Car insurance is becoming increasingly important to Lemonade's growth strategy, while autonomous-vehicle insurance creates a new opportunity at the intersection of insurance and emerging transportation technology.

At the same time, Lemonade continues expanding geographically and building its technology platform.

The company entered 2026 with approximately three million customers and reached 3.31 million customers by Q2. Its current strategy targets continued rapid growth while moving toward positive adjusted EBITDA.

For Wininger, the central challenge is turning Lemonade's technology advantage into a scalable insurance platform that can compete across multiple products and markets.

Key Facts About Shai Wininger

Category	Details
Full Name	Shai Wininger
Current Role	President & Co-Founder, Lemonade
Company	Lemonade, Inc.
Co-Founder	Daniel Schreiber
Lemonade Founded	2015
President Since	January 1, 2024
Previous Lemonade Roles	Co-CEO, CTO, Secretary, Treasurer
Current Lemonade CEO	Daniel Schreiber
Previous Company Founded	Fiverr
Fiverr Founded	2009
Fiverr Role	Founder & CTO
Core Expertise	Technology, Product, Engineering, Entrepreneurship
Lemonade Customers, Q2 2026	3.31 million
Lemonade IFP, Q2 2026	$1.43 billion
Q2 2026 Revenue	$294 million
Q2 2026 Gross Profit	$113 million
Public Company	Yes — NYSE: LMND

Current executive titles and career history are supported by Lemonade's SEC filings and official governance materials. The latest operating figures are from Lemonade's Q2 2026 investor materials.

Summary

Shai Wininger is the President and Co-Founder of Lemonade, a technology-driven insurance company using AI, automation, data, and digital distribution to reinvent the insurance experience.

Wininger co-founded Lemonade with Daniel Schreiber in 2015 after previously founding Fiverr in 2009. At Fiverr, he served as CTO and managed engineering, design, and product, helping build the technology infrastructure behind one of the world's major digital service marketplaces.

At Lemonade, Wininger initially served as CTO and later held multiple leadership roles, including Co-CEO. Since January 2024, he has served as President, while Daniel Schreiber remains CEO and Chairman.

His technology background has shaped Lemonade's strategy from the beginning. The company was built as a technology-native insurer rather than as a traditional insurance business with technology added later.

By Q2 2026, Lemonade had reached 3.31 million customers and $1.43 billion in In-Force Premium, while revenue reached $294 million.

In 2026, Wininger has been particularly involved in Lemonade's expansion of car insurance and the development of products for autonomous vehicles. Lemonade's Autonomous Car product uses driving data to price autonomous and human-driven miles differently, while the company continues expanding its car-insurance footprint across the United States.

Wininger's career therefore connects two technology transformations: Fiverr's transformation of digital services into an online marketplace and Lemonade's attempt to rebuild insurance around AI and software.