Senior Learning Designer, Leadership Development

About the role

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.

Responsibilities

• 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
• 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
• Build content managers can use the same day — conversation guides, templates, and reflection prompts that fit seamlessly into meetings and existing workflows
• 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

Requirements

• 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
• 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

Qualifications

• Experience with AI and its integration into workplace management
• Experience with remote and hybrid work environments

Skills

• Strong project management skills
• Excellent communication and interpersonal skills
• Ability to work independently and collaboratively
• Experience with data analysis and interpretation

Benefits

• Competitive salary range of $100,000 - $130,000 plus equity + benefits
• Flexible work schedule with 3 days per week in the Soho office

Pay

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.

Schedule

Lemonade offers a flexible work schedule with 3 days per week in the Soho office.

Things to know

• Lemonade is an equal opportunity employer committed to diversity and inclusivity
• We never discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status
• If you require reasonable accommodations due to religious beliefs, pregnancy, or disabilities, let us know at any time