Not your everyday company

Lemonade completely reinvented how insurance works. As a customer-centric tech company, we created an insurance experience that is smart, instant, and delightful.

At Lemonade, you'll be working with a group of like-minded makers, who get a kick out of moving fast and delivering great products. We surround ourselves with some of the smartest, most motivated, creative people who are filled with positive energy and good karma.

Unlike most publicly traded companies, we're nimble and efficient. We take pride in the fact that we still think and operate like a startup. We don't care much about titles and hierarchy and instead focus on innovation, bold moves, and challenging the status quo.

We're built as a lean, data-driven organization that relies on a common understating of objectives and goals to provide teams with autonomy and ownership. We don't like spending our days in meetings and we skip committees altogether. At Lemonade, there's no such thing as going over someone's head. We have zero tolerance for bureaucracy, office politics, and lean-back personalities.

As a Public Benefit Corporation and a certified B-Corp, we deliver environmental and social impact using our products and tech. Through our Giveback program, we partner with organizations such as the ACLU, New Story, The Humane Society, Malala Fund, American Red Cross, 360.org, charity: water, and dozens of others, and have donated millions towards reforestation, education, animal rights, LGBTQ+ causes, access to water, and more.

Awarded 'best workplace'

Best Workplace and Best-Led Company by Inc. Magazine

"World Changing" by Fast Company

Recognized as a World Changing Idea by Fast Company Magazine

Ranked #1 Home insurance in America

Won best renters and homeowners insurance in America by US News, and others

Best Pet Insurance in America

Rated "Best Overall Pet Insurance" by Better Homes & Gardens

Rated 4.9 on the App Store

Among the highest rated apps of all time

What you're applying for

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'll

• Lead 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

What you'll need

• 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

Things to know...

Lemonade is an equal opportunity employer committed to diversity and inclusivity. We never discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. If you require reasonable accommodations due to religious beliefs, pregnancy, or disabilities, let us know at any time.