Lemonade

We're looking for a User communication Product leader to own and evolve how Lemonade communicates with customers - across every product surface, channel, and AI-powered experience we ship. This isn't a traditional writing role. Lemonade puts the written word at the core of everything, and you get to lead it. You'll own our internal system that enables humans and AI to explain complex insurance moments simply, consistently, and at scale. You'll set the bar for what "Lemonade-y" means in practice, and work through the most advanced and nuanced communication challenges we face. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll: • Own product voice and communication quality through our internal system, setting the bar for clear, concise copy that reduces friction and turns confusing moments into intuitive ones - getting to the mind and heart of our users to drive real outcomes • Define how we use and scale UX copy, support macros, and AI-generated product communication across human and automated channels • Continuously improve output quality through training, evaluation, and feedback loops, and monitor copy quality across all product surfaces • Maintain and evolve communication guidelines in collaboration with stakeholders, positioning automation and scalable systems that enable teams to produce Lemonade-quality communication efficiently • Act as the subject-matter expert on what makes communication "Lemonade-y," ensuring alignment between human and automated experiences so customers receive a consistent voice regardless of channel • Define and promote best practices for integrating AI into customer-facing experiences while maintaining clarity, trust, and brand consistency • Bridge Product and customer-facing teams to ensure consistent, clear explanations across support macros, partner comms, inside sales, and agents • Partner with Support to identify recurring confusion points and address them at the source through copy, flows, automation, and education What you'll need: • 7+ years of experience in UX writing, content design, content strategy, or a related role within a product-led company • A portfolio that demonstrates your ability to turn complex, confusing moments into clear, intuitive experiences • Deep understanding of microcopy best practices across flows, modals, error states, and onboarding • Experience working with AI writing tools and a genuine curiosity for how automation shapes customer communication • Strong cross-functional collaboration skills - you're comfortable working with Product, Engineering, Support, and CX teams simultaneously • An eye for consistency and the ability to build systems, guidelines, and workflows that scale across teams • Data-driven mindset with comfort tracking copy quality, support ticket trends, and adoption metrics • Excellent written English with full professional fluency • Ability to work in an office environment most days of the week • Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture

We’re looking for a senior-level backend engineer to join our growing Engineering team in TLV. This role will require you to bring features to the finish line while collaborating closely with other developers, as well as with the Product, QA, Data, and Machine Learning teams—all with the goal of delivering a seamless, joyful experience for our customers. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you’ll: • Help build our products using microservices written in Typescript (using NestJS). • Leverage our in-house autonomous tools to manage all development flow, from setting up our development environment to creating git branches and deploying services to production • Collaborate closely with the Product team, in a self-sufficient squad to achieve the squad’s OKRs • Be the owner of your domain to ensure code quality, performance, and scalability of our products • Coach and mentor other developers and help them elevate their skills What you’ll need: • 6+ years working as a backend engineer • BSc in Computer Science or Mathematics (or equivalent experience) • Passionate about technology • Broad knowledge of modern backend frameworks, tools, and architecture • Experience working on high scale, production-grade projects • Past contributions to open source projects are a plus • Ready to work in an office environment most days of the week

We’re looking for a Senior Growth Product Manager with a passion for experimentation, data-driven decision-making, and creating seamless user experiences. You’ll join one of our high-impact growth teams, helping drive user acquisition, engagement, retention, and cross-sell opportunities. This role has the potential to unlock massive revenue growth - scaling from millions to billions. You’ll define and implement strategies that drive measurable impact, using deep customer insights, A/B testing, and iterative experimentation to fuel sustainable growth. As a strategic leader, you’ll set the vision for where we need to go and craft the roadmap to get us there - balancing business goals with customer needs. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Own and execute key parts of our growth strategy, from research to launch, focusing on user acquisition, retention, and monetization • Understand customer behavior and pain points, leveraging data, user research, and experimentation to uncover opportunities • Define and track key performance indicators (KPIs) to measure success and continuously optimize for impact • Lead continuous A/B testing and experimentation, using insights to drive iterative improvements • Work cross-functionally with Design, Engineering, Data Science, and Marketing to bring growth ideas to life • Challenge assumptions and rethink the status quo, pushing for bold, innovative approaches to growth What You’ll Need • 6+ years of experience as a product manager in a fast-paced, growth-focused environment • Deep expertise in growth methodologies, including A/B testing, conversion optimization, and engagement strategies • A data-first mindset, with strong analytical skills and experience leveraging insights to inform decisions • End-to-end product execution skills, from strategy and ideation to implementation and optimization • Exceptional communication and storytelling skills, with the ability to influence stakeholders at all levels • A hands-on, proactive mindset - you’re not afraid to dive in and make things happen • Ready to work in an office environment most days of the week

We're looking for a Senior Car Insurance Pricing Expert to help shape how Lemonade prices risk across our global business, from our Tel Aviv office. This isn't a traditional actuarial role. You'll sit at the intersection of Insurance, Data Science, Product, Engineering, and Business Strategy on our Insurance team, owning hard pricing and risk-management problems end to end. That means finding opportunities, designing better approaches, building scalable tools with technical teams, and turning insights into decisions that move growth, profitability, and risk selection forward. You might be a trained actuary, a pricing leader, a decision scientist, or a technically strong insurance operator who's built serious pricing capabilities. Formal credentials are a plus, but they're not the point. The point is whether you can use data, insurance intuition, statistical rigor, and AI-enabled tools to solve complex pricing problems better and faster than the industry standard. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Own and evolve core components of Lemonade's Car pricing strategy, bringing analytical rigor and product-minded creativity to how we price risk • Identify high-leverage opportunities across rating, underwriting, segmentation, risk selection, growth, profitability, and portfolio management • Build, evaluate, and improve Car pricing and risk models using actuarial methods, machine learning, AI-enabled workflows, and strong business judgment • Partner with Data Science, Product, Engineering, Finance, and Growth to turn pricing ideas into scalable capabilities • Translate complex pricing problems into clear product and platform requirements, helping teams build internal tools that make better decisions faster • Define and track key metrics - loss ratio, rate adequacy, conversion, retention, segmentation lift, and model performance - to keep decisions grounded in real impact • Make complex actuarial and pricing concepts clear and actionable for technical and non-technical audiences alike, and help build pricing acumen across the Tel Aviv team What you'll need • 8+ years of experience in Car insurance pricing, actuarial science, decision science, risk analytics, or a closely related field • A proven track record solving complex pricing, underwriting, segmentation, or risk-management problems with measurable business impact • Strong analytical instincts - knowing how to find signal in data, make decisions under uncertainty, and separate elegant analysis from useful analysis • Hands-on fluency with modern analytical tools, agentic AI capabilities, and code - including experience using generative AI, coding agents, or advanced automation to materially improve analytical workflows • Solid understanding of Car insurance pricing fundamentals, including rating plans, loss costs, rate adequacy, segmentation, model validation, telematics and financial performance. • Familiarity with predictive modeling methods such as GLMs, gradient boosting, random forests, clustering, and feature engineering • Experience building or modernizing pricing platforms, rating engines, underwriting tools, or internal decision-support software • Product-minded problem solving: the ability to turn a messy workflow, technical constraint, or business problem into a clear, prioritized path forward - with a track record of partnering with Product and Engineering teams to ship production-grade tools • Strong communication skills - you can explain pricing decisions, tradeoffs, and model outputs clearly to executives, engineers, product teams, and regulators • Comfort operating in a fast-moving environment where ownership matters, ambiguity is normal, and AI is part of how work gets done • Experience leading pricing work across multiple geographies, products, or regulatory environments is a strong plus • Formal actuarial credentials, such as Fellow or Associate of a recognized actuarial society, are a plus • Bachelor's degree in Actuarial Science, Mathematics, Statistics, Computer Science, Economics, Engineering, or a related quantitative field • Ready to work in an office environment most days of the week

We're looking for a Strategy & Ops Senior Lead, to drive profitability and growth while leading strategic initiatives that move Lemonade forward. You'll work as a "mini-COO" for our product lines, tackling the biggest business challenges while collaborating on cross-functional projects that take ideas from 0 to 1. This role sits at the intersection of strategy, operations, and execution - where data meets decision-making and where your leadership directly impacts our mission to transform insurance. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Drive profitability and growth strategies for our business as a strategic business partner • Lead cross-functional initiatives that span Product, Insurance, Finance, and Customer Operations teams • Take strategic projects from concept to execution, working across multiple stakeholder groups • Analyze complex business challenges and translate insights into actionable recommendations • Influence decision-making at the leadership level while building alignment across diverse teams • Navigate rapidly changing priorities and guide teams through strategic pivots • Partner with Product, Actuarial, Finance, and Revenue teams to optimize business performance What you'll need • 6+ years in management consulting (strategy and operations), business strategy, or business operations with leadership experience • Track record of driving impact and influencing decisions across multiple stakeholder groups • Ability to adapt quickly in a fast-moving environment while maintaining strategic focus • Strong analytical mindset with experience turning data into business strategy • Experience leading cross-functional projects and building consensus across diverse teams • Ready to work in an office environment most days of the week

We're looking for an Associate Insurance Product Manager to help grow Lemonade Car into the most loved car insurance on the planet. You'll join the Insurance Product team at a pivotal moment — working closely with Actuarial and Underwriting experts to shape coverage, pricing, and the product roadmap that drives profitable, scalable growth. Your work sits at the intersection of data, regulation, and real customer impact. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Develop new car product features that meet the needs of emerging customer segments and channels • Partner with Actuarial and Underwriting to define coverage, pricing, and eligibility requirements for Lemonade Car • Own the regulatory lifecycle for key product initiatives — from concept through production launch • Monitor and analyze performance metrics, spotting trends and recommending data-driven actions that keep the car business growing profitably • Research the competitive landscape and market trends to make sure Lemonade Car stays best-in-class • Collaborate with Insurance Operations, Engineering, and Data to bring product changes to market with speed and quality What you'll need • 4+ years of P&C insurance experience, with at least 2 years in personal lines product management • Bachelor's degree in Finance, Economics, Actuarial Science, Statistics, Insurance, or a related analytical field • Proven success managing products in a highly analytical, regulated environment • Strong analytical skills and confidence working independently with large data sets • Clear, methodical communication skills and a data-informed approach to decisions • Deep experience in car insurance is a strong plus • SQL skills, including building reports and dashboards, are a plus • Genuine enthusiasm for AI and a real commitment to growing alongside these tools — it's core to how we work here • Ability to work in a remote environment Please note that we are unable to sponsor applicants for work visas. Unfortunately, we cannot consider applicants from these states: Alaska, California, Colorado, Montana, Hawaii, New Mexico and Puerto Rico. Lemonade's US base salary range for this full-time position is $85,000 - $107,500 plus equity + benefits. Our salary ranges are determined by role, level, and location. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Our competitive total rewards package includes comprehensive health & wellness coverage, equity, a 401(k) plan with employer match, 20 paid vacation days, and parental leave. Speak to your recruiter to hear more about the specific salary range for your preferred location and our total rewards package. ||#LI-Remote||

We're looking for a Staff Product Manager to help us win new markets across Europe. You'll join our Product team to shape who we serve, what we offer, and how it feels from the first quote to the first claim. This is a zero-to-one build, not a localization project. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll: • Own the zero-to-one of market expansion, from personas and segmentation to packaging and value proposition • Spot the moments that matter most to customers and design experiences that feel local and still scale globally • Sweat the small details so hard moments feel comforting and routine ones feel a little fun • Build honest, transparent products that meet real customer needs • Use data and automation to free up our team for empathy and big-picture creativity • Set a clear product vision and make sure first versions are strong foundations for the next three years • Bring diverse teams to quick decisions, from first idea to launch What you'll need: • 7+ years of product management experience, including leading a market expansion or a high-stakes global launch • Strong product sense and a high bar for customer experience • A data-first approach to personas, segmentation, packaging, and pricing for new audiences • High agency - you find a way through obstacles instead of waiting for permission • Ability to influence stakeholders at every level and tell a clear story about how we'll win in new markets • Real curiosity about AI and a commitment to exploring how it can improve your work • Ready to work in an office environment most days of the week

We are looking for a Product Marketing Leader with deep strategic thinking and a passion for translating product value into clear, compelling customer narratives. In this role, you will sit at the intersection of product strategy, customer insight, and marketing execution, owning the storytelling behind our most important initiatives and ensuring consistency across every customer touchpoint. You will lead product value articulation end to end, from market and customer research, through defining core USPs and shaping launch narratives, to execution across landing pages, email, and full funnel marketing experiences. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Own positioning and messaging for new products, major features, and strategic initiatives, defining what is new, why it matters, and why now • Translate product strategy and capabilities into clear, differentiated customer value that resonates across segments • Shape launch narratives end to end, from early go-to-market alignment with product teams through post-launch optimization • Lead qualitative and quantitative customer research to uncover real motivations, needs, and objections, and use those insights to sharpen messaging • Guide copy and narrative direction across landing pages, lifecycle emails, and marketing funnels to ensure consistent and compelling product storytelling • Improve conversion and feature adoption by continuously testing, measuring, and refining how we communicate value • Reduce go-to-market friction by embedding messaging strategy early in the product development process • Partner closely with leadership and cross-functional teams to shape go-to-market strategy, align on product narratives, and strengthen customer-facing communication across channels What you'll need • 7+ years of experience in product marketing, ideally in a product-led environment • Proven ability to own positioning and messaging for products and features, not just execute against an existing strategy • Strong track record of leading or heavily contributing to product launches, from narrative and go-to-market planning through launch performance and iteration • Strong customer research capabilities, with experience using qualitative and quantitative insights to shape positioning and messaging decisions • Demonstrated impact on conversion, adoption, or product understanding, with a data-informed approach to measuring messaging effectiveness • Excellent cross-functional partnership skills, with experience working closely with Product, Growth, Design, and Marketing teams • Ability to work from the office most days of the week

What you're applying for Anyone can ship an AI agent. Shipping one that’s right ~98% of the time, with no human checking its work, takes different engineering. That’s what this team builds. We're looking for a Senior Backend Engineer to help push our AI customer-service agents closer to fully autonomous insurance service. You'd be joining the team behind the agent that talks to real customers every day over email, phone, chat, and SMS - handling policy questions, claims conversations, and verified documents end-to-end, with no human in the loop. This isn't a demo or a copilot. Real customers, real money, real stakes, every day. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Design, build, and own production LLM agent systems end-to-end - deciding how the agent thinks, what it's allowed to do, and how it fails safely • Work on our real-time voice agent, where the hard problems are conversational: interruptions, mid-sentence tool calls, and keeping response times imperceptibly fast • Shape the next generation of our knowledge base - how the agent's knowledge is structured, curated, and served, so answers stay grounded as coverage grows • Ship changes as controlled experiments, measure them against thousands of replayed real conversations on our in-house eval platform, and graduate winners into production • Track cost per conversation across millions of LLM calls and find the wins that cut spend without cutting quality • Own what the model knows and says - the customer context it sees, the limits on what it may reveal, and the guardrails against confident nonsense • Build and operate scalable backend services in TypeScript/Node on Kubernetes/AWS with deep observability - if you ship it, you own it What you'll need • 6+ years building production-grade backend systems that real users depend on • Hands-on experience shipping LLM-powered features to production, including honest reckoning with non-determinism, hallucination, and cost • An evaluation mindset - you don't call a change "better" without a measurement, and you're comfortable with the statistics that back that claim • A track record of debugging distributed systems in production, and the discipline to find root cause across service boundaries • Fluency with agentic coding tools like Claude Code or Cursor, including the habit of treating AI-generated code with a senior reviewer's skepticism • The ability to pull your own numbers, design your own experiments, and measure your own impact • Ready to work in an office environment most days of the week

We're looking for a Senior Product Designer who combines strong product thinking, UX, and visual craft with genuine curiosity about how AI is changing what we build — and how we build it. Designers at Lemonade work across customer-facing products, complex internal systems, design systems, and AI-powered experiences. You'll own projects end-to-end, collaborate closely across disciplines, and help explore new approaches to designing and building great products. This role sits within our Product Design team, based in Tel Aviv. Please only apply if you have an up-to-date online portfolio showcasing recent work. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. We don't expect designers to know every tool or model. We do expect genuine curiosity — using AI in your process, designing experiences that couldn't exist without it, and staying open to rethinking the work, not just accelerating it. In this role you'll • Create delightful user-facing products across web and mobile, turning complex problems into simple, intuitive experiences • Own the design process end-to-end — from understanding the problem and exploring solutions through validation and implementation • Collaborate closely with Product, Engineering, Data, and QA to shape products and drive decisions • Design AI-powered experiences and explore where AI can fundamentally improve a product, workflow, or experience • Use AI throughout your own design process to explore, build, iterate, and work more effectively • Design complex internal systems and contribute to the evolution of our design systems • Share strong product and design perspectives, and help raise the quality and capabilities of the wider design team What you'll need • 5+ years of experience designing digital products, with a portfolio demonstrating product thinking, UX, visual craft, and end-to-end ownership • Strong product thinking, with the ability to navigate ambiguity, simplify complex problems, and make thoughtful trade-offs • Excellent visual and interaction design skills, with strong attention to detail and mastery of Figma and prototyping • Experience creating and working with design systems • Hands-on experience using AI as part of your design or product development process • Curiosity to go beyond prompting — experimenting with AI, building new workflows, prototyping with it, and exploring how it changes both products and the way you work • Strong communication and collaboration skills, with the ability to take ownership and drive projects forward independently • A background in Visual Communication is an advantage — illustration, animation, motion, or coding skills are a plus too • Ability to work in an office environment most days of the week

We're looking for a Staff Product Designer to help shape the future of how we design at Lemonade — not just by doing great work, but by raising the bar for everyone around you. This role sits within our Product Design team, based in Tel Aviv. You'll take on the broadest, most complex design challenges we have — owning them end-to-end, driving decisions across teams and disciplines, and influencing how we think about product and design at a company level. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. We don't expect designers to know every tool or model. We do expect genuine curiosity — using AI in your process, designing experiences that couldn't exist without it, and staying open to rethinking the work, not just accelerating it. In this role you'll • Lead the design of our most complex, high-impact product areas — owning scope end-to-end from problem definition through delivery • Drive decisions across Product, Engineering, Data, and leadership, bringing design perspective into the room early and often • Mentor and elevate designers across the team — through feedback, collaboration, and raising the standard of what great work looks like • Communicate clearly and confidently to all audiences — from teammates to senior leadership, internally and externally • Shape how we approach AI-powered experiences, and help the wider team think bigger about what AI makes possible • Contribute to the strategic direction of our design systems and set the quality bar for craft across the team • Spot gaps in how we work and take ownership of fixing them — whether that's process, tooling, or how design shows up in the product org What you'll need • 7+ years of experience designing digital products, with a portfolio that demonstrates strategic thinking, exceptional craft, and measurable impact at scale • A track record of owning large, complex scopes end-to-end — from ambiguous problem to shipped product • Comfortable navigating complex organizations, aligning stakeholders, and moving work forward across disciplines • Strong mentorship instincts — you make the designers around you better, and you're intentional about it • Excellent communication skills, with the ability to present work, advocate for decisions, and inspire confidence in any room • Hands-on experience using AI as part of your design or product development process, and genuine curiosity about where it's taking the craft • Ability to work in an office environment most days of the week

We’re looking for a talent leader to oversee our global recruiting strategy and team. As AI transforms the future of work, finding the right people will become more nuanced, focused on identifying what uniquely human skills will take Lemonade to the next level. This isn’t about filling seats. It’s about understanding what skills drive impact, where the talent market is going, and how AI can absorb the mechanics so you can lead our quest to find “needle in a haystack” talent across the globe. We believe two things matter for every leadership role at Lemonade: leadership that sets the bar for excellence, builds high performing teams, and holds them accountable, and strategy that thinks several years ahead and turns ambitious plans into reality. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Be a magnet for exceptional talent. Use your strategic thinking and relationship-building superpowers to bring in top talent. Take on our most challenging searches and lead our small but mighty talent team • Build a skills-driven talent strategy. Evolve how we assess talent to measure unique human abilities for the things AI can’t, or shouldn’t, handle • Forecast like an analyst. Use your analytical thinking and AI fluency to build talent forecasts that inform the business • Drive operational excellence. Build efficient, AI-powered recruiting systems. Know the data, unblock your team, communicate effectively, and ship as if we needed it yesterday What we're looking for • 10+ years in talent, people, business development, relationship management, or related fields • Experience managing and leading global teams • AI appetite, with real examples of how you use AI today • Emotional intelligence that lets you move the business in ways AI can’t, and build deep connections with candidates, hiring managers, executives, and other stakeholders • Ready to work in an office environment most days of the week Please note that this is a global role. We are open to hiring this position in Tel Aviv or New York City.

We're looking for a Backend Engineer to help build and scale the Machine Learning Platform that powers how Lemonade uses AI across the business. You'll be part of the ML Platform team, designing the infrastructure that lets our data scientists move faster, ship smarter, and operate with confidence in production. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Design and build the foundational ML platform and AI agents to accelerate data science model delivery across all business units • Architect cloud-native microservices running on Kubernetes, using infrastructure-as-code to automate model deployment and management • Own the end-to-end ML lifecycle, covering training, testing, deployment, and real-time monitoring • Evaluate and choose the right tools and technologies based on workload demands and performance requirements • Collaborate with engineering, data science, and product teams to keep ML projects aligned with business goals • Identify and fix reliability, scalability, and performance gaps before they become problems What you'll need • 3+ years of software engineering experience, with a strong record of delivering high-scale, production-grade systems • Strong proficiency in Python • Hands-on experience with relational and NoSQL databases, and at least one major cloud platform (AWS, Azure, or GCP) • Experience with training, testing, deploying, and monitoring real-time or near real-time ML models in production • Fluent with AI-powered development tools like Cursor and Claude Code, and genuinely curious about what's next in GenAI, LLMs, and AI agents • Familiarity with AI concepts like RAG, embeddings, mixture-of-experts, prompt crafting, and LLM context engineering - an advantage • Sharp problem-solving instincts and the ability to move fast without cutting corners • Bachelor's or Master's degree in Computer Science, Engineering, Statistics, or a related field • Ready to work in an office environment most days of the week

We're looking for a Senior Director of Brand Marketing to own what Lemonade stands for, protect what makes it unmistakable, and make sure brand thinking shapes the biggest decisions the company makes - not just the assets that come after. You'll balance long-term brand building with short-term commercial impact, and serve as the executive voice on everything brand - across every market, channel, and touchpoint we operate in. This role sits at the center of the Marketing team, partnering directly with our founders and executive leadership. Two things matter for every leadership role at Lemonade: leadership that sets the bar for excellence, builds high-performing teams, and holds them accountable, and strategy that thinks several years ahead and turns ambitious plans into reality. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll: • Own the Lemonade brand end-to-end positioning, narrative, voice, and brand systems and act as the final internal authority on what's on-brand across every consumer touchpoint globally • Be the company's go-to person for brand, helping founders, executives, and cross-functional leaders make decisions that strengthen the brand, the business, and the customer experience • Lead world-class integrated campaigns from strategy through execution, including creative direction, external director and studio selection, and the executive feedback loop • Own the end-to-end production of brand and OOH campaigns - from briefing and vendor management through delivery, measurement, and iteration - ensuring creative work ships at scale and on time • Drive operational excellence across the creative function, building the systems, processes, and workflows that allow the team to deliver high-quality work consistently and efficiently • Create non-traditional brand activations, experiential moments, partnerships, and cultural ideas that make Lemonade more visible, more relevant, and harder to forget • Own global brand strategy, including localization, cultural adaptation, market-specific briefs, and the systems that keep Lemonade consistent as it grows • Define and track the brand health metrics that matter - awareness, consideration, distinctiveness, and mental availability - and turn those learnings into smarter strategy, priorities, and budget decisions • Build and lead the brand and creative team, setting the creative bar, running senior hiring, and mentoring the next generation of creative talent at Lemonade What you'll need: • You've built a distinctive consumer brand at a top-tier company or agency - people remember the work, and the work moved the business • A proven track record leading major integrated campaigns from concept to screen, working with external directors, production partners, agencies, and internal creative teams • Demonstrated operational experience managing large-scale creative production - OOH, brand, and integrated campaigns - with a strong grasp of timelines, budgets, and vendor relationships • Experience building or improving creative operations infrastructure: workflows, briefing systems, production pipelines, and cross-functional collaboration models • Exceptional taste and judgment - you can articulate exactly why brand work is or isn't working, and hold the bar without doing the work yourself • The ability to turn complex products into simple, human stories and make strong strategic decisions with incomplete information • Experience scaling brand footprints internationally, with real sensitivity to cultural nuance and what should or shouldn't change • The ability to influence and align founders, executives, and senior cross-functional partners around a single brand vision • You understand brand measurement well enough to connect decisions to business outcomes, without reducing the brand to a dashboard • Strong leadership skills with a track record of hiring, developing, and inspiring senior creative talent • Ready to work in an office environment most days of the week.

We're looking for a Senior Backend Engineer to help build and scale the Machine Learning Platform that powers how Lemonade uses AI across the business. You'll be part of the ML Platform team, designing the infrastructure that lets our data scientists move faster, ship smarter, and operate with confidence in production. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Design and build the foundational ML platform and AI agents to accelerate data science model delivery across all business units • Architect cloud-native microservices running on Kubernetes, using infrastructure-as-code to automate model deployment and management • Own the end-to-end ML lifecycle, covering training, testing, deployment, and real-time monitoring • Evaluate and choose the right tools and technologies based on workload demands and performance requirements • Collaborate with engineering, data science, and product teams to keep ML projects aligned with business goals • Identify and fix reliability, scalability, and performance gaps before they become problems What you'll need • 6+ years of software engineering experience, with a strong record of delivering high-scale, production-grade systems • Strong proficiency in Python • Hands-on experience with relational and NoSQL databases, and at least one major cloud platform (AWS, Azure, or GCP) • Experience with training, testing, deploying, and monitoring real-time or near real-time ML models in production • Fluent with AI-powered development tools like Cursor and Claude Code, and genuinely curious about what's next in GenAI, LLMs, and AI agents • Familiarity with AI concepts like RAG, embeddings, mixture-of-experts, prompt crafting, and LLM context engineering - an advantage • Sharp problem-solving instincts and the ability to move fast without cutting corners • Bachelor's or Master's degree in Computer Science, Engineering, Statistics, or a related field • Ready to work in an office environment most days of the week

We're looking for a Staff Growth Product Manager to own and scale a central growth domain inside our Car product team - the fastest-growing engine at Lemonade. Car is in hyper-growth with aggressive targets, and this role sits at the frontline of hitting them. You'll take on the biggest, hardest problems in car insurance and, by cracking them, ignite the next stage of our growth. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Own a core growth domain within Car end to end, from spotting the opportunity to shipping the solution and optimizing it live • Take on the biggest, hardest problems in car insurance, and turn solving them into the spark for our hyper-growth • Surface the strategy that gets us to our targets, then align leadership around it - you set the direction, not the other way around • Form the vision and roadmap, and drive execution across Car's teams until it's real in production • Connect the full picture of growth: user experience, pricing, marketing, regulation, driving and car data, data science models, segmentation, and market trends • Build AI-native experiences that give our customers a genuinely better service, including how we lead on autonomous-car insurance • Partner closely with our data analytics team, plus engineers, designers, data scientists, actuaries, marketers, and senior leaders to solve hard problems and move fast What you'll need • 7+ years in product management, ideally at a startup or product-led company • A track record of owning strategy end to end, finding the opportunity, aligning leadership, and shipping to production • Deep growth experience across acquisition, activation, engagement, and monetization • Strong analytical instincts and the ability to turn messy data into clear decisions, working hand in hand with data analytics • The communication and influence to align stakeholders across an entire organization • A hands-on, execution-focused mindset that stays close to the work through launch and beyond • Real enthusiasm for building with AI, it's core to how we work, not a side project • Ready to work in an office environment most days of the week

What you're applying for We're looking for an experienced SIU Investigator to help protect honest policyholders and keep sophisticated fraud networks from gaming the system — while making sure legitimate claims move fast. You'll join our Claims team at a pivotal moment, bringing specialized investigative expertise to high-risk files as we expand into key markets like Florida and keep pushing the boundaries of what modern fraud detection looks like. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Lead end-to-end SIU investigations on complex auto claims — Physical Damage, Bodily Injury, and PIP/Medical Payments — with full ownership from referral to resolution • Identify and dismantle multi-claim fraud networks, staged accident rings, and coordinated medical billing schemes using link analysis and pattern-recognition techniques • Apply deep working knowledge of Florida PIP statutes, medical fee schedules, and the 14-day treatment rule to counter state-specific fraud trends • Partner directly with our Data Science and Product teams to test and refine predictive fraud models, feeding real-world case intelligence back into automated detection • Investigate emerging digital fraud risks — AI-manipulated damage photos, synthetic media, and altered records — using the latest AI tools and digital research platforms • Support EUOs, state fraud bureau referrals, and case strategy alongside claims adjusters and legal counsel What you'll need • 5+ years of dedicated SIU or auto claims investigative experience, with a track record on complex, high-stakes cases • Deep Florida PIP and BI expertise — statutes, treatment windows, billing mill fraud, and EUO dynamics • Hands-on experience with intelligence platforms like ISO ClaimSearch, Accurint, TLOxp, or LexisNexis • Proven ability to investigate large-scale, multi-jurisdictional organized fraud rings and billing syndicates • Genuine curiosity about AI — both as an investigative asset and as a fraud threat vector you'll need to stay ahead of • A college degree, preferably in criminal justice, insurance, or a related field • Ability to work in a remote environment Please note that we are unable to sponsor applicants for work visas. Unfortunately, we cannot consider applicants from these states: Alaska, California, Colorado, Montana, Hawaii, New Mexico and Puerto Rico. Lemonade's US base salary range for this full-time position is $65,000 - $72,500 plus equity + benefits. Our salary ranges are determined by role, level, and location. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Our competitive total rewards package includes comprehensive health & wellness coverage, equity, a 401(k) plan with employer match, 20 paid vacation days, and parental leave. Speak to your recruiter to hear more about the specific salary range for your preferred location and our total rewards package. ||#LI-Remote||

We're looking for an experienced Recruiter to play a central role in our global team and help us maintain our unique culture and values. As part of the Global Talent team, you'll fully own and execute mid to senior-level hiring across Lemonade's functional teams. You'll source candidates through online and offline channels, including social platforms and professional networks, while partnering with hiring managers and teams across our locations. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll: • Act as a strategic full-cycle Recruiter for your stakeholder group • Influence the overall talent acquisition process with your expertise and insights • Use analytics to help managers and department leads stick to hiring timelines • Develop insightful talent mapping for key roles • Use AI tools to speed up sourcing, screening, and day-to-day recruiting work, and keep improving the efficiency of our processes • Promote employer branding through social media job postings and by hosting or joining career events and meetups • Support hiring managers in defining interview evaluation criteria and competencies, so interviews run efficiently and professionally What you'll need: • 5+ years of recruiting experience, with a recent in-house background • Proven ability to work in a team-based organization, collaborating cross-functionally and globally • Skill in developing recruiting strategies for sourcing, evaluating, and selecting senior talent • A firm grasp of recruiting metrics and KPIs, and the ability to use them to drive decisions • Experience in a high-performance environment where multiple projects and competing demands are the norm • Hands-on experience using AI tools in recruiting, such as for sourcing, screening, or automating workflows • Ability to work in an office environment most days of the week

We’re looking for a Senior Product Manager who’s experienced in planning, designing, and scaling world-class products. If you love tackling complex problems, cherish the power of automation and self-service, enjoy exploring the latest GenAI models, and are passionate about designing amazing customer experiences at scale, this one’s for you. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you’ll: In your day-to-day, you’ll be responsible to drive Lemonade’s automation efforts to the next level, to allow us to reach infinite scale. Our efforts are focused on automating all of the touch points we have with our customers— including handling their claims, replying to their questions to customer support, and reviewing risk factors. By doing so, we optimize our operational efficiency and drive delightful customer experience. • As part of your work you’ll get to use the latest GenAI tools and LLMs powered by our home grown internal tools. • You’ll collaborate closely with designers, engineers, data analysts, and stakeholders within our Customer Ops team. • With an in-depth knowledge of Lemonade’s customer-facing teams, products, and brand, you’ll create product strategies consistent with the company’s vision, and translate them into detailed requirements and prototypes. • You’ll prioritize tasks as needed, and come up with creative new ideas to expand our product functions, and improve scalability and automation efforts. What you’ll need: • At least 5 years experience working as a product manager in a successful startup / fast-growing company - a must • Hands on experience with building GenAI applications - a must • Capable of understanding complex processes, and identifying areas calling for improvement • Experience with automating manual processes - a big plus • Self-organized, process driven • Data-driven and analytical thinker • Fully fluent in English, with top-notch communication skills • Experience leading small, agile teams • Self-learning individual who reads constantly and loves to pass on their knowledge to others • Ready to work in an office environment most days of the week • Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture

We're looking for a Data Warehouse Tech Lead to drive the technical vision and execution of our data infrastructure that powers decision-making across all of Lemonade. You'll lead both the technology and the business coordination for our data warehouse — architecting scalable solutions while working closely with stakeholders and data providers to ensure our platform serves the entire organization's needs. This role combines deep technical leadership with strategic business partnership as we build Lemonade's next-generation data stack. We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work. Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools. In this role you'll • Lead technical architecture — design and develop scalable data warehouse solutions that support multiple products and serve the entire organization's analytics needs • Manage the technical roadmap — set strategy and guide execution for the Data Warehouse team, ensuring our platform evolves with business requirements • Drive business process coordination — translate business needs into technical requirements while establishing clear data contracts with R&D, Analytics, and external data providers • Establish and implement best practices — set technical standards for data warehouse architecture, performance tuning, and development methodologies that guide the entire team's approach to building scalable data solutions • Create and maintain sustainable data pipelines — build resilient systems capable of handling unstructured data and managing an evolving schema registry across diverse data sources • Implement advanced data modeling — create robust data structures using methodologies like dimensional modeling, and optimize ETL/ELT processes for our semantic layer • Establish data quality standards — build processes for schema evaluation, anomaly detection, and monitoring data completeness and freshness across all sources • Lead cross-team collaboration — work directly with Data Engineers, ML Platform Engineers, Data Scientists, Analysts, and Product Managers to align technical solutions with business goals What you'll need • 7+ years as a BI Engineer or Data Engineer, with 2+ in a technical leadership or architect role • Proven experience managing complex data warehouses that serve multiple products and entire organizations • Strong expertise in data modeling, ELT development, and data warehouse methodologies • Advanced SQL skills and hands-on experience with Snowflake or similar cloud-native data warehouse platforms • Extensive experience with dbt for data transformation and modeling • Python and software development experience (a strong plus) • Excellent communication skills — you can mentor technical team members and explain complex data concepts to business stakeholders • Ready to work in an office environment most days of the week • Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture