CLX Squad Lead, Contractor Operations

We're looking for a Senior Manager of External Operations & Strategy to help us build and run an external partner ecosystem that's as fast and rigorous as we are. You'll sit within our Property Claims organization, owning the end-to-end relationships with our Third Party Administrators and operational vendors - the people and systems that power our claims operations at scale. 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 Own the end-to-end strategy for TPAs and operational vendors from selection and onboarding through ongoing optimization and performance management Set and enforce rigorous KPIs and SLAs, holding external partners to the same standards of speed, care, and accuracy we hold ourselves to Partner with Product and Engineering to integrate vendors into our proprietary AI tools, pushing legacy partners toward a faster, tech-first way of working Build executive ready business cases using financial modeling to influence Loss Adjustment Expense and vendor budgeting decisions Lead regular quality audits and performance reviews, translating data into concrete plans that improve vendor output and cost efficiency Surface performance insights with Analytics and work directly with vendors to embed those insights into their day-to-day workflows What you'll need 5+ years in strategy, vendor management, or claims operations, ideally in a tech-forward or high growth environment 3+ years in a leadership role, with a track record of managing and scaling complex partner relationships Advanced data analysis skills a MUST, including SQL or BI tools, and the ability to turn large, imperfect datasets into clear financial decisions Demonstrated experience leading cross functional initiatives from kickoff to measurable results Executive level communication skills, you can influence a partner CEO and an internal Product lead in the same afternoon At Lemonade we welcome candidates who are enthusiastic about learning and adapting to the exciting world of technology and AI, as a commitment to ongoing growth in this field is a fundamental part of our culture Insurtech or startup experience is a strong plus Ability to work in a remote environment College Degree 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 $110,000 - $135,000 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. Speak to your recruiter to hear more about the specific salary range for your preferred location. ||#LI-Remote||