Senior Learning Designer, Leadership Development

We're looking for a Senior Learning Designer, Leadership Development Lead to help Lemonade's managers become the kind of leaders people actually want to work for. On our People team, you'll define what great management means at a company built on autonomy, accountability, and constant change — and then build the experiences, tools, and frameworks that make it real. As AI takes on more operational work, the bar for human leadership rises. This role exists to meet that moment. We believe three things matter for every role at Lemonade: driven 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 Define what great leadership looks like at Lemonade in an AI-first, autonomous org — then build the frameworks, language, and tools that make it concrete for managers day-to-day Own our Manager Seminars end-to-end: gather feedback, u