We're looking for a User communication Product leader to own and evolve how Lemonade communicates with customers - across every product surface, channel, and AI-powered experience we ship.
This isn't a traditional writing role. Lemonade puts the written word at the core of everything, and you get to lead it. You'll own our internal system that enables humans and AI to explain complex insurance moments simply, consistently, and at scale. You'll set the bar for what "Lemonade-y" means in practice, and work through the most advanced and nuanced communication challenges we face.
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:Own product voice and communication quality through our internal system, setting the bar for clear, concise copy that reduces friction and turns confusing moments into intuitive ones - getting to the mind and heart of our users to drive real outcomes
Define how we use and scale UX copy, support macros, and AI-generated product communication across human and automated channels
Continuously improve output quality through training, evaluation, and feedback loops, and monitor copy quality across all product surfaces
Maintain and evolve communication guidelines in collaboration with stakeholders, positioning automation and scalable systems that enable teams to produce Lemonade-quality communication efficiently
Act as the subject-matter expert on what makes communication "Lemonade-y," ensuring alignment between human and automated experiences so customers receive a consistent voice regardless of channel
Define and promote best practices for integrating AI into customer-facing experiences while maintaining clarity, trust, and brand consistency
Bridge Product and customer-facing teams to ensure consistent, clear explanations across support macros, partner comms, inside sales, and agents
Partner with Support to identify recurring confusion points and address them at the source through copy, flows, automation, and education
7+ years of experience in UX writing, content design, content strategy, or a related role within a product-led company
A portfolio that demonstrates your ability to turn complex, confusing moments into clear, intuitive experiences
Deep understanding of microcopy best practices across flows, modals, error states, and onboarding
Experience working with AI writing tools and a genuine curiosity for how automation shapes customer communication
Strong cross-functional collaboration skills - you're comfortable working with Product, Engineering, Support, and CX teams simultaneously
An eye for consistency and the ability to build systems, guidelines, and workflows that scale across teams
Data-driven mindset with comfort tracking copy quality, support ticket trends, and adoption metrics
Excellent written English with full professional fluency
Ability to work in an office environment most days of the 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
Skills Required
- 7+ years of experience in UX writing, content design, content strategy, or a related role within a product-led company
- Portfolio demonstrating the ability to turn complex, confusing moments into clear, intuitive experiences
- Deep understanding of microcopy best practices across flows, modals, error states, and onboarding
- Experience working with AI writing tools
- Strong cross-functional collaboration skills with Product, Engineering, Support, and CX teams
- Ability to build communication systems, guidelines, and workflows that scale across teams
- Data-driven mindset with comfort tracking copy quality, support ticket trends, and adoption metrics
- Excellent written English with full professional fluency
- Ability to work in an office environment most days of the week
- Enthusiasm for learning and adapting to AI
Lemonade Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Lemonade and has not been reviewed or approved by Lemonade.
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Healthcare Strength — Cigna-administered medical plans provide multiple options (EPO/OAP/OAPIN/HDHP) alongside dental, vision, prescription coverage, disability, and life/AD&D. 2026 plan materials and state notices indicate broad essential health benefits with mainstream networks.
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Retirement Support — A tiered 401(k) match structure is documented, offering meaningful employer contributions when employees save. This complements equity grants/RSUs that are commonly included in total rewards.
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Leave & Time Off Breadth — Employee-reported baselines around defined PTO and company holidays, plus flexible sick time, position time off as a strength. Parental leave is frequently described as generous for the U.S. context, though candidates should confirm current specifics.
Lemonade Insights
What We Do
Our mission is simple: Create the world’s most loved insurance through technology and social impact. As a certified Public Benefit Corporation and B-Corp, Lemonade is constantly challenging how the insurance industry does business. We’re creating an experience that is fast, affordable, and hassle-free across renters, homeowners, pet, life and car insurance. And through our annual Giveback program, in which leftover premiums are donated to charities our customers choose, we’ve donated nearly $5 million to a variety of organizations in need.
Why Work With Us
We’ve set out to make insurance loveable, fast, simple, and socially impactful - words that aren’t often associated with this industry. We’re a Certified B-corp, the only US insurance company to never invest in polluting industries, and our annual Giveback program has donated nearly $5 million globally to nonprofits in need.
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