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 CLX Squad Lead to take direct operational ownership of our external contract workforce handling property claims. You'll sit within our property leadership team, managing contract adjusters across both day-to-day desk claims and catastrophe surges - making sure our external operation runs with the same precision, speed, and quality we hold ourselves to internally. This is a hands-on leadership role with real accountability for how our contractor engine performs.

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

• Provide direct day-to-day oversight, performance management, and guidance to contract adjusters handling desk claims - both steady-state and catastrophe (CAT).
• Track key metrics - turnaround times, customer satisfaction, file quality - and drive the team to hit them consistently
• Manage real-time staffing levels, capacity modeling, and inventory flow so the contractor desk handles volume spikes without losing speed or quality
• Own the file audit process for contractor handling, delivering clear, actionable feedback that enforces compliance, policy adherence, and technical accuracy
• Handle high-tier customer and file escalations directly, coaching contract adjusters on how to spot and prevent friction before it reaches the customer
• Partner with property leadership to make sure contractor workflows keep pace as internal processes and AI tools evolve

What you'll need

• 5+ years of property claims handling experience, with deep knowledge of renters, dwelling, desk operations, and CAT claims management
• 2+ years in a supervisory or team lead capacity, specifically managing desk adjusters or external contract and TPA workforces
• A proven track record of holding third-party contractors and temporary adjusters to strict performance metrics, SLAs, and quality standards
• A data-driven mindset - you track what matters, spot what's off, and know how to course-correct
• Hands-on experience with Xactimate, XactAnalysis, and modern web-based claims management tools
• Active property adjuster license in your resident state
• Comfort working with and learning new technology, including AI-powered tools that are changing how we work
• A bachelor's degree in a related field, or equivalent operational experience
• Ability to work in a remote environment

Please note that we are unable to sponsor applicants for work visas.

Unfortunately, we cannot consider applicants from these states: Alaska, California, Colorado, Montana, Hawaii, New Mexico and Puerto Rico.

Lemonade's US base salary range for this full-time position is $80,000 - $92,500 plus equity + benefits. Our salary ranges are determined by role, level, and location. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Our competitive total rewards package includes comprehensive health & wellness coverage, equity, a 401(k) plan with employer match, 20 paid vacation days, and parental leave. Speak to your recruiter to hear more about the specific salary range for your preferred location and our total rewards package.

#LI-Remote

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.