Anyone can ship an AI agent. Shipping one that’s right ~98% of the time, with no human checking its work, takes different engineering. That’s what this team builds.
We're looking for a Senior Backend Engineer to help push our AI customer-service agents closer to fully autonomous insurance service. You'd be joining the team behind the agent that talks to real customers every day over email, phone, chat, and SMS - handling policy questions, claims conversations, and verified documents end-to-end, with no human in the loop. This isn't a demo or a copilot. Real customers, real money, real stakes, every day.
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.
Design, build, and own production LLM agent systems end-to-end - deciding how the agent thinks, what it's allowed to do, and how it fails safely
Work on our real-time voice agent, where the hard problems are conversational: interruptions, mid-sentence tool calls, and keeping response times imperceptibly fast
Shape the next generation of our knowledge base - how the agent's knowledge is structured, curated, and served, so answers stay grounded as coverage grows
Ship changes as controlled experiments, measure them against thousands of replayed real conversations on our in-house eval platform, and graduate winners into production
Track cost per conversation across millions of LLM calls and find the wins that cut spend without cutting quality
Own what the model knows and says - the customer context it sees, the limits on what it may reveal, and the guardrails against confident nonsense
Build and operate scalable backend services in TypeScript/Node on Kubernetes/AWS with deep observability - if you ship it, you own it
6+ years building production-grade backend systems that real users depend on
Hands-on experience shipping LLM-powered features to production, including honest reckoning with non-determinism, hallucination, and cost
An evaluation mindset - you don't call a change "better" without a measurement, and you're comfortable with the statistics that back that claim
A track record of debugging distributed systems in production, and the discipline to find root cause across service boundaries
Fluency with agentic coding tools like Claude Code or Cursor, including the habit of treating AI-generated code with a senior reviewer's skepticism
The ability to pull your own numbers, design your own experiments, and measure your own impact
Ready to work in an office environment most days of the week
Skills Required
- 6+ years building production-grade backend systems that real users depend on
- Hands-on experience shipping LLM-powered features to production, addressing non-determinism, hallucination, and cost
- Experience building and operating scalable backend services in TypeScript/Node on Kubernetes/AWS with strong observability
- Track record of debugging distributed systems in production and finding root cause across service boundaries
- An evaluation mindset with comfort using statistics to measure and validate changes
- Fluency with agentic coding tools (e.g., Claude Code, Cursor) and skeptical senior review of AI-generated code
- Ability to pull own metrics, design experiments, and measure impact
- Willingness to work in an office environment most days of the week
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 — Health coverage is delivered via mainstream Cigna medical options, with multiple plan types and supplemental health protections. This signals broad networks and a robust core healthcare offering.
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Retirement Support — A company 401(k) match is part of the package and is positioned alongside other core financial benefits. This provides structured retirement savings support as a standard element of total rewards.
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Leave & Time Off Breadth — PTO is presented as generous, alongside paid sick time and strong parental leave with a return-to-work program. These time-off provisions extend beyond the basics and support work-life needs.
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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