We're looking for a Staff Product Manager to help architect the scalable platforms that solve our most complex systemic challenges. You'll sit at the intersection of automation, AI, and infrastructure - owning the strategy and execution for core capabilities that move Lemonade's platform forward. This role lives within our Product team and carries real visibility across the organization.
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'llLead zero-to-one strategy and execution for critical automation platforms - building the scalable infrastructure that powers seamless workflows and measurable efficiency gains
Map and untangle complex, multi-step logic to identify where self-service and AI can replace manual effort, then drive those initiatives through to scale
Build with the latest GenAI tools and LLMs, alongside our homegrown internal tooling, to create capabilities that intelligently manage high-stakes touchpoints
Partner closely with engineers, designers, data analysts, and internal stakeholders to shape product strategy, then translate it into detailed requirements and working prototypes
Own the roadmap for foundational infrastructure, prioritizing solutions that expand capabilities and reduce friction for internal teams and end-users alike
Mentor across the organization, championing rigorous problem-solving, systems thinking, and a culture of continuous learning
10+ years of product management experience in a successful startup or fast-growing company
Hands-on experience building and deploying GenAI applications and working with LLMs at scale
A proven track record of automating complex, manual processes and scaling foundational workflows
Strong ability to deconstruct and optimize intricate, multi-step systems and data-heavy user journeys
A data-driven, analytical approach - someone who turns platform metrics into meaningful product decisions
Fluent English with sharp communication skills across technical and non-technical audiences
A self-organized, process-driven approach to managing competing priorities and leading cross-functional agile teams
A genuine curiosity for new technology - you read constantly, experiment often, and love sharing what you learn
Ready to work in an office environment most days of the week
Skills Required
- 10+ years of product management experience in a successful startup or fast-growing company
- Hands-on experience building and deploying GenAI applications and working with LLMs at scale
- Proven track record of automating complex, manual processes and scaling foundational workflows
- Strong ability to deconstruct and optimize intricate, multi-step systems and data-heavy user journeys
- A data-driven, analytical approach to turn platform metrics into meaningful product decisions
- Fluent English with sharp communication skills across technical and non-technical audiences
- Self-organized, process-driven approach to managing competing priorities and leading cross-functional agile teams
- Genuine curiosity for new technology and continuous learning
- Ready 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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