We're looking for an Operations Manager to help us build and run the automation systems that power our customer experience at scale. You'll sit within our CX organization, leading projects that span LLM pipeline optimization, robotic process automation, and the cross-functional work that keeps it all moving in the same direction. 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 end-to-end execution of CX automation projects - from sprint planning with LLM associates to pipeline updates - keeping everything tied to customer experience goals * Own reporting on automation performance, identifying trends and translating data into clear, actionable recommendations for the team and stakeholders * Partner with cross-functional teams to implement new CX initiatives, aligning on objectives and removing blockers before they slow things down * Monitor and optimize LLM pipeline outputs, ensuring responses stay effective, accurate, and aligned with how we want customers to feel * Stay close to emerging technologies and industry shifts, bringing forward recommendations that keep our automation work ahead of the curve * Facilitate clear, consistent communication across teams so everyone - from engineers to ops leaders - understands what we're building and why What you'll need * 4+ years in a customer experience or operations role, with real ownership of projects and cross-functional initiatives * 2+ years of hands on experience with customer service automation tools, including LLMs and related technologies * Developing real, working solutions via vibe coding preferred * A builders mindset and thought partner in AI systems is required * Sharp analytical skills and the ability to turn messy, real-world data into decisions that actually move the needle * Strong organizational skills and the ability to manage multiple workstreams without dropping the ball * A bachelor's degree in a related field * 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 $100,000 - $115,000 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||