We're looking for a Senior Operations Manager to lead AI-powered automation across Lemonade's Customer Operations organization — and fundamentally change how we serve customers at scale. This isn't an oversight role. It's a builder role. You'll own the automation strategy across CX, Claims, and Underwriting, sitting within our centralized Customer Operations team, partnering daily with Product and Engineering to shape the roadmap and drive our AI-first operational transformation from concept through production 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 automation roadmap across Customer Ops — setting priorities, defining requirements, and driving delivery of AI-powered solutions across digital CX, Claims, and Underwriting workflows in close partnership with Product and Engineering * Serve as the primary ops-side counterpart to Product on GenAI programs, shaping how automation solutions are built, tested, and operationalized — and closing the feedback loop so what gets built actually works in production * Build hands-on — designing agent architectures, engineering prompt workflows, and vibe-coding automation tools. You're not just managing builders; you are one * Build executive-ready business cases with rigorous financial analysis and forecasting that influence budgeting, headcount, and automation investment decisions * Lead and develop a team of builders focused on GenAI integration and workflow automation, fostering a culture where experimentation, technical craft, and operational impact are equally valued * Drive GenAI initiatives from pilot to production — owning the full lifecycle from proof-of-concept through scaled deployment across CX, Claims, and Underwriting * Champion an AI-first mindset across Customer Ops, setting the pace for how the team thinks about automation and keeping the organization on the frontier of emerging tools and techniques * Own the tooling strategy and vendor feedback loop, ensuring operational needs shape tooling decisions through structured feedback, testing, and roadmap input to Product and external partners What you'll need * 6+ years in operations, program management, or a similar role — preferably in technology, insurance, or fintech * 3+ years of hands-on experience building AI and automation solutions: prompt engineering, workflow automation, AI agent design, or vibe coding — a portfolio of things you've built, not just programs you've managed * 2+ years of team leadership with a track record of developing high-performing individual contributors * Demonstrated ability to partner cross-functionally with Product and Engineering, translating operational needs into technical requirements and driving shared outcomes * Strong data fluency — comfortable with SQL, BI tools, and turning metrics into decisions that stick * Executive-level communication skills — able to distill complexity, influence decisions, and drive alignment across levels and functions * A builder's mindset — you default to building the solution, not writing the requirements doc for someone else to build * A genuine, demonstrated commitment to staying on the frontier of AI tools, techniques, and applications — enthusiasm alone isn't enough * 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 $140,000 - $155,000 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||