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, update content, and sunset or redesign learning that no longer fits how we operate — keeping everything practical, immediately applicable, and true to how we lead - Partner with Manager Partners and use Manager Effectiveness data to identify skill gaps, then design learning experiences to fill them — with a focus on organizational change, AI-human team dynamics, and coaching in remote and hybrid environments - Experiment rapidly with new learning formats — treat each program like a product launch, with clear hypotheses, fast iteration, and honest retrospectives - Meet managers where they are by using a variety of formats: self-paced eLearning, podcasts, Slack nudges, live seminars, practical toolkits, and one-page resources - Build content managers can use the same day — conversation guides, templates, and reflection prompts that fit seamlessly into meetings and existing workflows - Create spaces for peer-to-peer learning through cohort discussions, live seminars, and office hours that surface what great management looks like and help leaders grow from each other - Use surveys, usage data, and feedback to track engagement; partner with People Insights to measure whether learning is improving team performance and retention — and evolve the strategy based on what you find WHAT YOU'LL NEED - 4+ years of experience in learning design, leadership development, or management training — you understand what managers actually need, not just what looks good on a slide - Startup or high-growth company experience — you're comfortable with ambiguity, fast change, and building from scratch - An ownership mindset: you spot problems, propose solutions, and take accountability for outcomes without waiting to be asked - Ability to design practical, immediately useful content that managers can apply right away — not theoretical frameworks that collect dust - Background in people management or close partnership with managers — you've either led a team or worked alongside them closely enough to understand their real challenges - Experience with learning management systems, content creation tools, and data analysis to measure learning impact - Strong written and verbal communication skills, especially for translating leadership concepts into tools people actually use - A collaborative approach with experience working across People, Operations, and Leadership teams - Deep understanding of modern management challenges, especially in remote and hybrid environments and AI-integrated workplaces - Ability to work in our Soho office 3 days per 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 *Please note that we are unable to sponsor applicants for work visas Lemonade's US base salary range for this full-time position is $100,000 - $130,000 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. Speak to your recruiter to hear more about the specific salary range for your preferred location.