CLX Squad Lead, Contractor Operations

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||