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Shai Wininger

@shai_wininger • 29,329 subscribers

Tech entrepreneur🎗️🇮🇱🇺🇸. CoFounder and President @ Lemonade (NYSE:LMND), CoFounder of Fiverr (NYSE:FVRR). Mixer of Tech, Design and AI.

Shorts

Thank you Ted Cruz for the Lemonade shout-out during today’s hearing on AV safety. “... Lemonade have lower premiums for vehicles using Full Self Driving Mode, reflecting growing confidence and growing evidence that these systems reduce risk." - Senator Ted Cruz Streamlined regulation is important for the safe deployment of AVs and can help reduce human error and save lives on the road.

Thank you Ted Cruz for the Lemonade shout-out during today’s hearing on AV safety. “... Lemonade have lower premiums for vehicles using Full Self Driving Mode, reflecting growing confidence and growing evidence that these systems reduce risk." - Senator Ted Cruz Streamlined regulation is important for the safe deployment of AVs and can help reduce human error and save lives on the road.

55,047 views

Let's talk about agentic product design. Every company has its own design process. What has always worked for me is spending long studio hours with our product team, dissecting things into pieces and putting them back together. In those sessions we look at value, usability, simplicity, aesthetics, behavior, storytelling, generics, and emotional mapping. I've been crafting products this way for as long as I can remember. Product work at Lemonade isn't for the faint of heart. This obsession over every detail is hard work, but I believe it yields better results and builds stronger talent. One of the things I love about our design and product team is how this process became a second nature to them. Feedback is fast, professional, and tension free. But in our latest session, something was different. One of our designers used Figma and Cursor to build a mockup that was so advanced, it was almost ready to be shipped. It was an incredible glimpse into a world where a single designer working on top of modern low code infrastructure will be able to launch production grade experiences for products with millions of customers, and with LoCo, I expect this to become a reality at Lemonade in just a few quarters. But there's a problem to watch out for. An interesting phenomenon I've noticed over the years is that the higher the fidelity of the work being reviewed, the more defensive people become. When someone shows up with something polished, they tend to resist feedback. They've already fallen in love with what they built, and it's hard for them to accept rejection. Radical candor feedback works best at an early stage of the project, before people get attached and feel the need to defend their work. This session was no exception. Because the work was so advanced, the review became binary, and its maker became defensive. Happily, we all caught ourselves in time to acknowledge this new dynamic and started figuring out how to go back to obsessing about every corner radius, shade of white, and word. When reviewing agentically coded designs, we'll try having our designers bring in more than one option, as well as the open Cursor project so we can make changes in real time if needed. We'll see how it goes, and if this is of interest, I'll update what we learn.

Let's talk about agentic product design. Every company has its own design process. What has always worked for me is spending long studio hours with our product team, dissecting things into pieces and putting them back together. In those sessions we look at value, usability, simplicity, aesthetics, behavior, storytelling, generics, and emotional mapping. I've been crafting products this way for as long as I can remember. Product work at Lemonade isn't for the faint of heart. This obsession over every detail is hard work, but I believe it yields better results and builds stronger talent. One of the things I love about our design and product team is how this process became a second nature to them. Feedback is fast, professional, and tension free. But in our latest session, something was different. One of our designers used Figma and Cursor to build a mockup that was so advanced, it was almost ready to be shipped. It was an incredible glimpse into a world where a single designer working on top of modern low code infrastructure will be able to launch production grade experiences for products with millions of customers, and with LoCo, I expect this to become a reality at Lemonade in just a few quarters. But there's a problem to watch out for. An interesting phenomenon I've noticed over the years is that the higher the fidelity of the work being reviewed, the more defensive people become. When someone shows up with something polished, they tend to resist feedback. They've already fallen in love with what they built, and it's hard for them to accept rejection. Radical candor feedback works best at an early stage of the project, before people get attached and feel the need to defend their work. This session was no exception. Because the work was so advanced, the review became binary, and its maker became defensive. Happily, we all caught ourselves in time to acknowledge this new dynamic and started figuring out how to go back to obsessing about every corner radius, shade of white, and word. When reviewing agentically coded designs, we'll try having our designers bring in more than one option, as well as the open Cursor project so we can make changes in real time if needed. We'll see how it goes, and if this is of interest, I'll update what we learn.

17,558 views

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We’re starting to roll out direct integration with Tesla vehicles, removing the need for a UBI device in our Pay Per Mile product. This makes activating Lemonade Car on Teslas effortless and lets us cut hardware and shipping costs, helping lower prices for Tesla drivers even further. Tesla's API also provides richer and more accurate driving behavior data than traditional UBI devices, enabling us to offer better rewards and discounts for safe driving and FSD usage.

We’re starting to roll out direct integration with Tesla vehicles, removing the need for a UBI device in our Pay Per Mile product. This makes activating Lemonade Car on Teslas effortless and lets us cut hardware and shipping costs, helping lower prices for Tesla drivers even further. Tesla's API also provides richer and more accurate driving behavior data than traditional UBI devices, enabling us to offer better rewards and discounts for safe driving and FSD usage.

1,647,180 views • 8 months ago

Meet the Lemonade Timeline - One of our secret weapons, kept under covers… until now. We started working on its foundations 10 years ago, before we wrote a single line of insurance code, and it has since become a core component of our Bionics Platform and Blender. 🧵>>

Meet the Lemonade Timeline - One of our secret weapons, kept under covers… until now. We started working on its foundations 10 years ago, before we wrote a single line of insurance code, and it has since become a core component of our Bionics Platform and Blender. 🧵>>

114,488 views • 6 months ago

What it feels like to report a Lemonade Car claim. Pick a recommended repair shop and get a tow dispatched in seconds.

What it feels like to report a Lemonade Car claim. Pick a recommended repair shop and get a tow dispatched in seconds.

76,701 views • 7 months ago

A quick glimpse into Lemonade’s new AI voice agents platform, now in the final stages of development—demoed by Shay, one of our principal engineers in Tel Aviv

A quick glimpse into Lemonade’s new AI voice agents platform, now in the final stages of development—demoed by Shay, one of our principal engineers in Tel Aviv

57,210 views • 1 year ago

Validation remains the main bottleneck in agentic coding. As agents generate features quickly, humans are left to review and validate their work: security, stability, performance, compliance, UX, design, copy, and more. This is not scalable. Truly unattended, production-ready agentic coding requires rethinking how quality is built into the process. Our approach is to embed validation at the very beginning of feature creation. We've built AI tools that analyze product specs, generate test plans, orchestrate complex testing with natural language, and emulate human interaction to "try" new features. The Lemonade AI Validation Framework is still in its early days, but we're already seeing strong signals of scalability and impact. In July, our tiny QA team ran 82,167 complete quality tests, covering 95% of customer-facing production code. Using traditional methods, this would likely have taken 10x the headcount and 10x the time. Below is a small part of the system in action:

Validation remains the main bottleneck in agentic coding. As agents generate features quickly, humans are left to review and validate their work: security, stability, performance, compliance, UX, design, copy, and more. This is not scalable. Truly unattended, production-ready agentic coding requires rethinking how quality is built into the process. Our approach is to embed validation at the very beginning of feature creation. We've built AI tools that analyze product specs, generate test plans, orchestrate complex testing with natural language, and emulate human interaction to "try" new features. The Lemonade AI Validation Framework is still in its early days, but we're already seeing strong signals of scalability and impact. In July, our tiny QA team ran 82,167 complete quality tests, covering 95% of customer-facing production code. Using traditional methods, this would likely have taken 10x the headcount and 10x the time. Below is a small part of the system in action:

26,509 views • 9 months ago

Just upgraded our Dutch customers with a new Uniclient experience. Uniclient is a major part of our L2 stack. It allows our engineers to build beautiful, pixel-perfect experiences across multiple platforms using a single codebase and a rich framework that automatically adjusts to locales, screen sizes, device types, and more. We used to need separate engineering teams to support our iOS, Android, mobile web, and desktop web experiences. No more. Uniclient makes our engineering team exponentially faster when building frontend experiences for onboarding, policy management, and claims. In the vid you can see Uniclient running in a desktop browser. It's our Dutch product displayed in English (great for expats).

Just upgraded our Dutch customers with a new Uniclient experience. Uniclient is a major part of our L2 stack. It allows our engineers to build beautiful, pixel-perfect experiences across multiple platforms using a single codebase and a rich framework that automatically adjusts to locales, screen sizes, device types, and more. We used to need separate engineering teams to support our iOS, Android, mobile web, and desktop web experiences. No more. Uniclient makes our engineering team exponentially faster when building frontend experiences for onboarding, policy management, and claims. In the vid you can see Uniclient running in a desktop browser. It's our Dutch product displayed in English (great for expats).

16,149 views • 10 months ago

Love the new Lemonade singing ads

Love the new Lemonade singing ads

15,061 views • 2 years ago

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