Learning Designer, Skills

What You’re Applying For

We’re looking for a Learning Designer to help our Makers build the human skills they need to thrive in an AI-first future. You’ll design learning experiences that actually work and stick—turning concepts like adaptability, motivation, and efficiency, into something people genuinely want to engage with.

This role is critical as Lemonade transforms into the most autonomous organization in the world. While we’re AI-first in our operations, the human skills that complement our technology are what set us apart. You’ll be at the center of helping our team develop these essential capabilities through innovative, engaging learning experiences.

• Design and build highly engaging, bite‑sized learning journeys (videos, AI roleplays, interactive seminars) to develop core human skills like adaptability and efficiency
• Experiment with and pilot a diverse portfolio of fresh learning formats, including AI coaching bots and chat‑based modules, to target different learning styles
• Develop social learning activities across Slack and live sessions to foster a culture of continuous skill sharing and development
• Define and track behavioral change metrics (using Lemonade’s skills heatmap) to measure learning effectiveness and iterate on program design
• Partner with cross‑functional leaders, communications, and subject experts to ensure learning content is real, relevant, and tied to business needs
• Collaborate with People Analytics to align learning design with the company’s skills measurement and talent development strategy
• Research and integrate cutting‑edge learning methodologies, especially those leveraging AI for personalization and enhanced skill acquisition

• 3+ years of experience in learning design, content creation, or a related field
• Bachelor’s degree in Education, Psychology, Instructional Design, or related field (or equivalent experience)
• Hands‑on experience with AI tools and their application in content generation and learning (for experimenting with AI roleplays and coaching bots)
• Experience with learning management systems, content creation tools, and data analysis for learning effectiveness
• Strong verbal and written communication skills, with a knack for making personal development feel approachable (not cheesy)
• Adaptability, drive, and an efficiency mindset that thrives in a human‑AI collaborative environment
• Experience designing soft skills training or behavioral change programs is a huge plus
• 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 – $100,000 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.

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.