Lemonade

We're looking for a business-minded, technically strong leader to lead Business Applications at Lemonade and play a key role in building a more autonomous company. You'll work across the company to unpack complex problems, spot where technology creates real leverage, and lead a team that turns those opportunities into working solutions, from AI agents and automation to custom builds, integrations, and enterprise platforms. 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 • Get deep into how teams operate, understanding their goals, economics, workflows, and constraints to identify the highest-leverage opportunities for technology • Build toward a more autonomous Lemonade by identifying where work can be fundamentally redesigned through agents, AI, and software, then leading the team in making it real • Own problems end-to-end, from framing the problem and shaping the solution through implementation, adoption, and measurable impact • Shape a forward-deployed BizApps model where the team works close to the business, moves quickly, prototypes fast, and shares accountability for results • Lead and grow a strong team that combines business understanding, product thinking, and technical depth, raising the bar for ownership, curiosity, and speed • Build a point of view on where technology creates the most leverage across Lemonade, then turn that into a portfolio of initiatives you drive from opportunity to measurable impact What you'll need • 7+ years leading complex technology initiatives, ideally in consulting, digital transformation, or a client-facing environment where you've owned both the problem and the outcome • Exceptional structured problem solving, you can quickly understand how a business or function works and what drives its outcomes, break down ambiguous problems, and identify where technology can create the most leverage • Strong technical fluency across architecture, APIs, integrations, data, and automation, enough to shape solution design, evaluate tradeoffs, and confidently guide technical decisions • Hands-on familiarity with modern AI capabilities, including LLMs, agents, and AI-enabled development, and genuine curiosity about where it's headed • A track record of leading complex technology initiatives from problem definition and solution design through implementation, adoption, and measurable business impact • Strong product thinking, you start with the problem, challenge requirements, prioritize by impact, and care whether what you build actually gets used • Strong executive communication and stakeholder management, you can turn complexity into a clear point of view, influence senior leaders, and drive decisions across functions • A college degree in a relevant field • 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 Senior Compliance Analyst to help build and strengthen compliance processes across Lemonade's growing portfolio of P&C insurance products. You'll sit within our Compliance team, supporting leaders and partnering with Insurance Operations and Product to monitor existing processes, stand up new ones, and make sure we're operating compliantly across Car, Home, Renters, and Pet — in an increasingly complex state regulatory environment. This role calls for someone who's organized, sharp, and confident translating regulatory complexity into clear, actionable guidance. 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 • Build and implement new compliance processes from scratch — structured, efficient, and built to scale • Develop policies and procedures that streamline operations and keep pace with regulatory requirements across all P&C lines • Provide compliance guidance, coaching, and feedback to key leadership as Lemonade continues to grow across Car, Home, Renters, and Pet products • Build strong working relationships across Compliance, Insurance Operations, and Product, and with colleagues across the broader business • Drive continuous improvement through AI and automation, finding smarter ways to manage compliance at scale • Manage multiple priorities and tight deadlines without letting standards or attention to detail slip • Support company-wide compliance projects as they arise What you'll need • 4+ years of P&C personal lines insurance compliance or risk management experience • Demonstrated persuasive writing skills — able to communicate issues clearly and translate technical and insurance requirements for different audiences • Strong organizational skills, with comfort managing multiple priorities in a fast-paced environment • Working knowledge of risk management principles across any line of business • Fluency with G-Suite and Slack as everyday work tools • A bachelor's degree in Business, Insurance, Risk Management, or a related field is a plus • 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 $90,000 - $103,500 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 highly analytical and detail-oriented User Acquisition Manager to join our Paid Acquisition team. You'll manage and scale global campaigns, leveraging data, advanced models, and AI tools to drive performance and optimize budget allocation across key activities. 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 end-to-end management of global, large-scale search and YouTube campaigns • Drive performance through deep data analysis, experimentation, and continuous iteration • Lead measurement, reporting, and budget allocation decisions for your channels • Identify growth opportunities by tracking industry trends, emerging platforms, and new technologies • Use AI tools to enhance campaign performance, automation, and decision-making • Combine strategic thinking with hands-on execution across multiple initiatives • Partner with Product, Creative, and Analytics to maximize impact and alignment What you'll need • 3+ years of experience managing global, large-scale B2C PPC campaigns focused on YouTube and Search (budgets of $150K+/month) • Experience with social platforms is a strong advantage • Strong analytical skills and a data-driven mindset • Proven track record of driving performance at scale • Strong project management and cross-functional collaboration skills • Ability to thrive in a fast-paced, high-ownership environment • Ready to work in an office environment most days of the week

We're looking for an Insurance Product Manager to help build the most loved car insurance on the planet. You'll be part of the Insurance Product team, working closely with Actuarial, Insurance Operations, and Underwriting to grow Lemonade Car profitably — shaping coverage, pricing, and the product roadmap that drives it all forward. From connected cars to rating plan sophistication, you'll own meaningful work that moves the product and the business. 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 products that meet the needs of emerging customer segments — including connected and autonomously driven cars • Advance our countrywide Car strategy through forms, coverages, policy language, and rating plan improvements that keep our protection cutting-edge • Partner with Actuarial and Underwriting to develop coverage, pricing, and eligibility requirements that balance innovation with financial soundness • Build product specification documents, define project requirements, and work with the Product team to prioritize and ship features that make a real difference for customers • Collaborate with Insurance Operations to move product changes through regulatory approval and into production — smoothly and fast • Research distribution channels, market trends, and competitor moves, turning findings into recommendations that grow the business • Measure the impact of product changes to support smarter decisions and ensure the product keeps evolving in the right direction What you'll need • 7+ years of P&C experience, with at least 5 years in personal lines insurance product development, product management, or state management • Bachelor's degree in Business, Insurance, Finance, Economics, Statistics, or a related field • Strong analytical skills and sharp attention to detail — you identify trends early and turn them into action • A strategic, ownership-driven mindset — you challenge the status quo and bring creative solutions to the table • Strong technical skills — SQL, Python, Looker, or similar tools, including experience building dashboards or reports, preferred • Solid Microsoft Office or Google Suite skills • Excellent organizational and project management skills, with the ability to manage multiple complex priorities in a fast-moving environment • Strong written and verbal communication skills, and a natural collaborator across teams • 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 $110,000 - $135,000 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||

What you're applying for We're looking for a Car Claims Advocate to help customers navigate one of the most stressful moments in their lives — a car accident or loss — with clarity, speed, and genuine care. You'll sit within our Claims team, owning auto property damage liability claims from first notice to resolution, and making sure every customer feels heard and fairly treated along the way. 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 • Investigate and process auto property damage claims — including theft and fire losses — in line with company policy and applicable state and federal laws • Gather and evaluate police reports, records, and witness statements to determine claim legitimacy and liability • Interview claimants and witnesses, explaining coverage decisions in plain language without leaning on jargon • Collaborate with legal counsel and other teams to move complex claims forward quickly and professionally • Maintain accurate, detailed records of all claim activity to keep things compliant and transparent • Contribute to team KPIs and continuous improvement — your work directly shapes how customers experience Lemonade What you'll need • 1+ years of auto property damage claim-handling experience • Working knowledge of insurance laws and regulations • Lemonade expects all advocates to hold a license in good standing — if you don't have one yet, we'll support you in getting licensed within your first 3 months • Strong analytical and critical thinking skills, with sharp written and verbal communication to match • Comfort working independently and collaborating closely with a distributed team • Proficiency with claims management software and Google Workspace • Bachelor's degree in a related field, or equivalent professional experience • 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 $51,000 - $58,500 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 architect the scalable platforms that solve our most complex systemic challenges. You'll sit at the intersection of automation, AI, and infrastructure - owning the strategy and execution for core capabilities that move Lemonade's platform forward. This role lives within our Product team and carries real visibility across the organization. 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 zero-to-one strategy and execution for critical automation platforms - building the scalable infrastructure that powers seamless workflows and measurable efficiency gains • Map and untangle complex, multi-step logic to identify where self-service and AI can replace manual effort, then drive those initiatives through to scale • Build with the latest GenAI tools and LLMs, alongside our homegrown internal tooling, to create capabilities that intelligently manage high-stakes touchpoints • Partner closely with engineers, designers, data analysts, and internal stakeholders to shape product strategy, then translate it into detailed requirements and working prototypes • Own the roadmap for foundational infrastructure, prioritizing solutions that expand capabilities and reduce friction for internal teams and end-users alike • Mentor across the organization, championing rigorous problem-solving, systems thinking, and a culture of continuous learning What you'll need • 10+ years of product management experience in a successful startup or fast-growing company • Hands-on experience building and deploying GenAI applications and working with LLMs at scale • A proven track record of automating complex, manual processes and scaling foundational workflows • Strong ability to deconstruct and optimize intricate, multi-step systems and data-heavy user journeys • A data-driven, analytical approach - someone who turns platform metrics into meaningful product decisions • Fluent English with sharp communication skills across technical and non-technical audiences • A self-organized, process-driven approach to managing competing priorities and leading cross-functional agile teams • A genuine curiosity for new technology - you read constantly, experiment often, and love sharing what you learn • Ready to work in an office environment most days of the week

We're looking for a product-minded IT leader to help Lemonade scale how teams get work done internally. You'll lead IT in Tel Aviv, manage a team of IT Solutionists, and build more autonomous Maker experiences - partnering across Product, Engineering, and Security to turn business needs into coherent strategies, systems, and automations using AI-powered products. 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 • Build and execute the Autonomous Maker Experience across the employee lifecycle, workplace technology, and technical support • Manage and develop IT Solutionists into stronger owners, builders, and advisers • Partner with leadership to identify, frame, and prioritize high-impact automation and AI opportunities • Apply problem decomposition and system design to turn incomplete ideas into clear plans and recommendations • Personally prototype and build automations, agents, workflows, and internal tools • Own cross-functional AI opportunities from discovery through rollout, adoption, and impact measurement • Own the Tel Aviv tech experience - networks, AV, MSPs, vendors, budgets, AI governance, and Security partnership • Build solutions that fit cohesively into Lemonade's wider agentic systems and Maker experience What you'll need • 7+ years across IT engineering, internal products, automation, business systems, technical operations, or adjacent roles • 3+ years leading and developing technical teams • Strong problem abstractions and the ability to structure and solve ambiguous business problems • Technical credibility to work as a peer with Product, Engineering, Operations, and Security • Strong understanding of AI, APIs, data flows, integrations, MCPs, security, and scalable system design • Experience with tools such as Claude, Cursor, Workato, or similar platforms • Comfort prototyping with Python, TypeScript, Ruby, or comparable languages • Strong communication and upward-management skills • A track record of creating direction, developing others, and shipping meaningful outcomes • Ready to work in an office environment most days of the week