Shai Wininger

Shai Wininger is a veteran tech entrepreneur and inventor, who most recently co-founded Lemonade, a licensed insurance company powered by artificial intelligence and behavioral economics. He previously founded Fiverr.com, the world’s largest marketplace for creative and professional services.

Most Recent

Lemonade's New Push: Zero Everything

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With Zero Everything, Lemonade customers will no longer need to pay deductibles and have their rate increased when filing claims.

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Lemonade: World’s First Live Policy

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Up until now, changing a deductible or coverage amounts or adding a valuable meant contacting customer support. Not any more.

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Lemonade: From Local to Everywhere

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As Lemonade gets ready to roll out across the U.S., it offers four tips for other startups on the "local vs. global" debate.

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The Third Wave of AI

By Paul Carroll

After the initial wave of AI efforts and then the generative AI phenomenon that began two years ago, you'll hear a lot in 2025 about AI that can act as our agents.

Insurance Fraud Rises as AI Powers Scams

Insurers must balance sophisticated fraud prevention with seamless customer experiences in an AI-driven landscape. Here's how. 

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Dashcams Combat Rising Wave of Insurance Fraud

As dashcam adoption surges, these devices are becoming crucial weapons against rising insurance fraud and staged accidents.

2

5 Client Retention Strategies for Insurance Agents

The lingering effects of rising premiums, coverage restrictions and evolving client expectations are making retaining business and maintaining strong relationships paramount.

3

Secret Powers Behind Super Insurance Agents

Three technologies are transforming insurance agents into digital-age concierges for their customers.

4

How to Tackle Third-Party Security Challenges

As insurance firms grapple with rising cyber threats, effective B2B identity management becomes crucial for protecting sensitive data.

5

Keys to Commercial Property Insurance Management

Data-driven technologies reshape commercial property insurance as managers tackle evolving risks and regulatory demands.

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ITL Recommends

What AI Means for Compliance

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Insurance Thought Leadership

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From Trust to Technology: The Tipping Point for Insurance Customers

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ITL Partner: Majesco

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How to Find the Right Carrier Partners

Beyond Silos: Strengthening Operational Resilience with Integrated Risk Management

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8 Trends Shaping the Future of Insurance in 2025

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ITL Partner: Majesco

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Insurance Industry Embraces Tech, Trust in 2025

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A Step-by-Step Guide to Using AI in Insurance

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Frederik Bisbjerg

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AI Revolutionizes Insurance Underwriting

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Artificial Intelligence