Lemonade
Customer Experience
SeniorCustomerOpsAutomationManager
Neural analysis suggests this role is
optimal for Senior candidates.
“Senior Customer Ops Automation Manager at Lemonade. Skills: AI-powered automation, process management, cross-functional coordination. Own the automation roadmap. Serve as primary ops-side counterpart to Product”
What You'll Achieve.
fundamentally change how we serve customers at scale; drive our AI-first operational transformation from concept through production scale; closing the feedback loop so what gets built actually works in production; operational impact are equally valued; scaled deployment across CX, Claims, and Underwriting
Industry & Context.
turning metrics into decisions that stick
unable to sponsor applicants for work visas, cannot consider applicants from these states: Alaska, California, Colorado, Montana, Hawaii, New Mexico and Puerto Rico
What They're Looking For.
Must Have
6+ years in operations, program management, or a similar role, 3+ years of hands-on experience building AI and automation solutions: prompt engineering, workflow automation, AI agent design, or vibe coding, 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, data fluency — comfortable with SQL, BI tools, and turning metrics into decisions that stick, Executive-level communication skills, A builder's mindset, A genuine, demonstrated commitment to staying on the frontier of AI tools, techniques, and applications, Ability to work in a remote environment
Nice to Have
preferably in technology, insurance, or fintech
What You'll Do.
Own the automation roadmap
Serve as primary ops-side counterpart to Product
Build executive-ready business cases
Lead and develop a team
Drive GenAI initiatives from pilot to production
Champion an AI-first mindset
Own the tooling strategy and vendor feedback loop
How You'll Work.
Team & Collaboration
partnering daily with Product and Engineering; Serve as the primary ops-side counterpart to Product; Demonstrated ability to partner cross-functionally with Product and Engineering
Communication Scope
Executive-level communication skills
Process & Methodology
program management
Full Job Description
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 - Driv
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