Compliance Manager

We're looking for a Compliance Manager to help us build and run a best-in-class compliance issue management function across Lemonade's growing portfolio of insurance products. You'll sit within our compliance team, owning the full lifecycle of issue identification, tracking, remediation, and reporting — working across Insurance Operations, Agency, Claims, and Product to keep Lemonade ahead of regulatory risk as we scale. This role calls for someone who brings sharp analytical instincts, a builder's mindset, and the confidence to drive senior leadership toward smart, risk-based decisions. 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 end-to-end compliance issue management — logging, tracking, prioritizing, and reporting on issues across the organization with real-time visibility for stakeholders Synthesize data to surface thematic trends, root causes, severity levels, and business impact before they become bigger problems Build and validate remediation plans with business owners that address root causes and prevent recurrence, not just close tickets Make prioritization recommendations to senior leadership backed by data, independent judgment, and a clear-eyed view of regulatory risk Work directly with regulators to resolve issues, including navigating initial misalignment with confidence and clarity Develop and apply AI and automation tools to improve how issues are tracked, reported on, and remediated Partner with compliance managers and business leaders to shape best practices and build cross-functional reporting metrics that actually get used What you'll need 7+ years of regulatory or compliance experience in US personal lines insurance, with a strong focus on issue management, risk mitigation, or internal audit Deep technical knowledge of the insurance policy lifecycle, state regulatory environments, and coverage across car, pet, home, and renters products Demonstrated ability to identify systemic themes from isolated incidents and translate complex regulatory risks into clear, actionable guidance for senior leadership A builder's mindset — a track record of using technology, automation, or AI tools to eliminate manual work and make compliance processes faster and smarter Comfort working in a highly technical, fast-paced environment where AI, machine learning, and automation are core to how the business runs Working knowledge of monitoring and testing practices, root cause analysis methodologies, and corrective action planning Hands-on experience with issue tracking or GRC systems — Jira, ServiceNow, AuditBoard, or similar Fluency with G-Suite and Slack as everyday work tools A bachelor's degree in a related field Ability to work in a remote environment 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 $115,000 - $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. 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||