lemonade - Senior Customer Ops Automation Manager
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Requirements
• 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.
Responsibilities
• 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
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