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.

Six Things

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Ignore Musk's Promise of Tesla Robotaxis

By Paul Carroll

While autonomous cars have made real progress lately, there's no reason to pay any attention to Musk's tease for a robotaxi announcement in August.

What to Know About Geospatial Technology

With climate change increasing risk, GIS allows for accurate risk assessment that goes even deeper than ZIP code level.

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Underwriters' Productivity Can Double

Michael Reilly, a managing director at Accenture, says underwriters only actually underwrite for 30% of their day -- but can soon get to 60%.

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Super Election Year Boosts Risks of Political Violence

Businesses need to protect their people and property with continuity planning, increased security and, perhaps, relocation of inventory.

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AI and a Vision for Safer Roads

AI not only encourages safer driving but also provides a route to transparent and accurate risk assessment, for fairer underwriting. 

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How Life Insurers Can Leverage Generative AI

The use of generative AI for coding for in-house applications is set to be the next big thing in 2024.

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Data Modernization in Insurance (Part 2)

The transformation of RGA's data and analytics operations offers a potential blueprint.

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Revolutionizing Customer Engagement: The Impact of Omnichannel Experiences in the Insurance Industry

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Underwriters' Productivity Can Double

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Insurance Thought Leadership

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Ignore the Doom and Gloom: Insurtech is Thriving

Ignore the Doom and Gloom: Insurtech is Thriving

The Surprises Lurking in Your Underwriting Rules

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Why CX Still Suffers in Insurance...and How to Improve It!

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Realignment in Insurance: Strategic Priorities for Success

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ITL Partner: Majesco

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Buyer's Guide & Evaluation Checklist for AI-Powered IDP Software

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Disaster Fraud — The Dark Side of Insurance Claims

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ITL Partner: FRISS

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