Lemonade · 7 hours ago
Learning Designer, Manager Learning
United States
Full-time
Remote
Mid Level
$75K/yr - $100K/yr
3+ years expLemonade is looking for a Learning Designer to enhance the leadership capabilities of its managers. This role involves designing effective learning experiences that address modern management challenges, particularly in an AI-driven environment, to improve team performance and retention.
Artificial Intelligence (AI)Financial ServicesInsuranceInsurTech
No H1B
Responsibilities
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
Qualification
Required
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 a remote environment
Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture
Benefits
Equity
Benefits
Company
Lemonade
Lemonade is a digital insurance company that uses artificial intelligence and behavioral economics.
1001-5000 employees
Funding
Current Stage
Public CompanyTotal Funding
$618.5MKey Investors
General CatalystSoftBankAllianz
2023-06-29Post Ipo Equity· $150M
2020-07-02IPO
2019-09-01Secondary Market· $1.5M
Leadership Team
Daniel Schreiber
Chief Executive Officer
Shai Wininger
Co-Founder, Co-CEO
Recent News
The Motley Fool
2026-02-03
2026-02-03
2026-01-23
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