Jobs
Required Skills
Learning Design
Product Management
Communication
Technical Knowledge
AI Knowledge
We're looking for a Learning Partner to be the go-to learning person for our Product and R&D teams. You'll bridge the gap between our core L&D team and the makers who build Lemonade's customer experience, taking company-wide development and making it work for designers, engineers, product managers, and researchers driving our innovation.
This role is critical as Product and R&D lead our transformation into the most autonomous organization in the world. You'll help the teams that design and build our AI-powered future stay at the cutting edge while developing the human skills that make great products possible.
We believe three things matter for every role at Lemonade: drive 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:
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Be Product and R&D's learning connector
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Serve as the main point of contact between Product, Engineering, Design, and Research teams and L&D. Help translate company-wide learning into development that makes sense for builders, creators, and innovators.
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Adapt learning to fit maker reality
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Take our overall L&D strategy and make it work for Product and R&D's unique challenges- rapid iteration, technical complexity, user research, and shipping features that millions use daily.
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Create tech-specific skill development
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Design learning around emerging technologies, design thinking, user research methods, and technical leadership. Build development paths that complement technical expertise with strategic thinking and collaboration skills.
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Champion AI-first product development and AI-driven learning
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Help Product and R&D teams confidently integrate AI into their workflows, from AI-assisted coding to AI-powered user research to designing AI-native customer experiences. Design learning experiences that leverage AI tools.
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Build learning that fits maker workflows
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Create ways for Product and R&D teammates to learn while shipping features, conducting research, or solving technical challenges. Design skill-building that happens naturally between sprints and releases.
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Share maker insights with L&D - Give the central team feedback on learning gaps, technical training needs, and what's working for Product and R&D professionals.
WHAT YOU’LL NEED:
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Adaptability, drive, and an efficiency mindset - we believe these matter most in human-AI collaboration.
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5+ years of experience in product management, engineering, design, or research-you understand the technical and creative challenges Product and R&D teams face daily.
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Natural ability to get people excited about learning new technologies, methodologies, and approaches to building great products.
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Strong communication skills and comfort facilitating discussions about technical topics, product strategy, or cross-functional collaboration.
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Experience working in product development, whether in engineering, design, PM, or research- you speak the language and understand the pressures of shipping.
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Proactive mindset for spotting learning opportunities around new technologies, design trends, or research methods before they become competitive advantages.
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Collaborative approach with experience working across product development functions and translating between technical teams and business goals.
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Understanding of how AI and emerging technologies can enhance product development and user experiences.
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Ready to work in an office environment most days a week
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Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture.
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About Lemonade

Lemonade
PublicInsurance company.
201-500
Employees
New York City
Headquarters
$1.2B
Valuation
Reviews
2.8
7 reviews
Work Life Balance
1.2
Compensation
2.0
Culture
1.1
Career
1.5
Management
1.0
15%
Recommend to a Friend
Pros
Remote work options available
First job experience opportunity
Intensive feedback for learning
Cons
Toxic management and micromanagement
Poor work-life balance and long hours
High employee turnover
Salary Ranges
15 data points
Junior/L3
Senior/L5
Junior/L3 · Statistical Reporting Analyst
1 reports
$80,301
total / year
Base
$69,826
Stock
-
Bonus
-
$80,301
$80,301
Interview Experience
1 interviews
Difficulty
4.0
/ 5
Duration
21-35 weeks
Interview Process
1
Application Review
2
Phone Screen
3
Technical Interview
4
Behavioral Interview
5
Final Round
Common Questions
Technical Knowledge
Behavioral/STAR
Past Experience
Case Study
News & Buzz
Privium Fund Management B.V. Invests $7.76 Million in Lemonade, Inc. $LMND - MarketBeat
Source: MarketBeat
News
·
5w ago
So long, frozen juice from concentrate. The once-popular canned drink leaves shelves this year - CBC
Source: CBC
News
·
5w ago
Lemonade turns self-driving cars from threat to opportunity - Financial Times
Source: Financial Times
News
·
5w ago
After Leaping 29% Lemonade, Inc. (NYSE:LMND) Shares Are Not Flying Under The Radar - simplywall.st
Source: simplywall.st
News
·
5w ago