Senior Manager, Insurance Operations

We're looking for a Senior Manager to fundamentally reshape how insurance filings get done at Lemonade. This role sits at the intersection of AI platform design, regulatory operations, and change leadership — and you'll own it end to end, working closely with our Product, Engineering, Actuarial, and Compliance teams inside Insurance Operations. 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 filing platform and automation initiatives from concept through rollout — scoping, building, testing, and iterating in close partnership with Product and Engineering - Map filing workflows and regulatory requirements continuously to identify the highest-impact opportunities for AI integration, automation, and systemic efficiency gains - Drive adoption of new tools and workflows across the insurance org, translating platform capabilities into clear value for stakeholders - Build and lead the IO platform team focused on owning and scaling filing tooling, fostering a culture where experimentation, regulatory credibility, and operational impact are equally valued - Set and hold the bar for filing quality, speed, and compliance as automation takes on more of the work — ensuring what gets built performs in a regulated environment - Establish the operating model, governance, and feedback loops that let the platform team build with speed and rigor WHAT YOU’LL NEED - 6+ years in insurance, with meaningful exposure to filings, regulatory operations, or compliance - 3+ years leading teams, with a track record of managing technically strong ICs and holding them accountable to outcomes - Direct experience with automation and process improvement, required - Experience identifying manual or inefficient operational workflows and replacing them with technology-enabled solutions that improve speed, accuracy, and cost efficiency - Hands-on fluency with LLMs like Claude or ChatGPT — you know how to build prompts, map logic, and use AI to multiply your output, not just talk about it - Strong project management and stakeholder communication skills: you move work forward through others, translate between technical and operational, and don't lose momentum when priorities shift - Advanced data analysis skills and the ability to independently extract insights that drive platform decisions - A builder's mentality: energized by ambiguity, focused on outcomes, and comfortable creating structure where there isn't any *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 $130,000 - $152,500 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||