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