Senior Learning Designer, Leadership Development

We are looking for a Learning Designer to help Lemonade's managers become the kind of leaders people actually want to work for. You'll keep our Manager Seminars fresh and build new learning that tackles real leadership challenges—like managing in an AI-first world or leading through constant change.

This role is crucial as we scale our autonomous organization. Great managers are what make our AI-first culture work for humans. You'll be designing the learning experiences that help our leaders navigate the unique challenges of managing at Lemonade—from coaching remote teams to leading through rapid AI adoption. This position is a critical part of the People Ops team, directly impacting team performance and retention as we continue to grow and embrace new technologies.

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

• Own our existing Manager Seminars from end-to-end. Gather feedback, update content, and ensure all learning is practical, immediately applicable, and aligned with how we actually lead at Lemonade.

• Partner with Manager Partners and use Manager Effectiveness data to proactively identify skill gaps. Design new learning experiences to fill these gaps, focusing on areas like organizational change management, AI-human team dynamics, and coaching in remote/hybrid environments.

• Leverage a variety of content formats to meet managers where they are, including self-paced learning (eLearning, podcasts, Slack nudges), live seminars, practical toolkits, and one-page resources.

• Design content—such as templates, conversation guides, and reflection prompts—that managers can seamlessly use in their day-to-day work, meetings, and existing workflows.

• Build spaces for peer-to-peer learning—including cohort discussions, live seminars, and office hours—to showcase what great management looks like and help leaders grow from each other's successes.

• Utilize surveys, usage data, and feedback to track content engagement. Partner with People Insights to determine if manager learning is improving team performance and retention, and use those insights to continually evolve the learning strategy.

What you'll need

• 3+ years of experience in learning design, leadership development, or management training—you should understand what makes managers tick and what they actually need

• Bachelor's degree in Education, Psychology, Business, or a related field (or equivalent experience)

• Ability to design practical, immediately useful content that managers can apply right away (not theoretical frameworks)

• Experience with learning management systems, content creation tools, and data analysis for measuring learning impact

• Excellent written and verbal communication skills, especially for translating leadership concepts into actionable tools

• Adaptability, drive, and an efficiency mindset — we believe these matter most in human-AI collaboration

• Background in people management or close partnership with managers—you've either been one or worked closely with them to understand their real challenges

• Collaborative approach with experience partnering across People, operations, and leadership teams

• Understanding of modern management challenges, especially in remote/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

Unfortunately, we cannot consider applicants from these states; Colorado, California, Montana, Hawaii, New Mexico and Puerto Rico.

Lemonade's US base salary range for this full-time position is $75,000 - $87,500 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. Speak to your recruiter to hear more about the specific salary range for your preferred location.