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