Compliance Manager

About the Role

We're seeking a Compliance Manager to build and manage a best-in-class compliance issue management function across Lemonade's expanding insurance product portfolio. You'll be part of our compliance team, overseeing the entire lifecycle of issue identification, tracking, remediation, and reporting. Collaborating with Insurance Operations, Agency, Claims, and Product teams, you'll help Lemonade stay ahead of regulatory risks as we scale.

Responsibilities

• Own end-to-end compliance issue management, including logging, tracking, prioritizing, and reporting issues with real-time visibility for stakeholders.
• Synthesize data to identify thematic trends, root causes, severity levels, and business impact before issues escalate.
• Build and validate remediation plans with business owners to address root causes and prevent recurrence.
• Make data-driven prioritization recommendations to senior leadership, balancing regulatory risk and business needs.
• Work directly with regulators to resolve issues, navigating misalignments with confidence and clarity.
• Develop and apply AI and automation tools to enhance issue tracking, reporting, and remediation processes.
• Partner with compliance managers and business leaders to establish best practices and create cross-functional reporting metrics.

Requirements

• 7+ years of regulatory or compliance experience in US personal lines insurance, with a focus on issue management, risk mitigation, or internal audit.
• Deep technical knowledge of the insurance policy lifecycle, state regulatory environments, and coverage for car, pet, home, and renters products.
• Proven ability to identify systemic themes from isolated incidents and translate complex regulatory risks into actionable guidance for senior leadership.
• A builder's mindset with a track record of using technology, automation, or AI to streamline compliance processes.
• Comfort working in a fast-paced, highly technical environment where AI, machine learning, and automation are central to operations.
• Working knowledge of monitoring, testing practices, root cause analysis, and corrective action planning.
• Hands-on experience with issue tracking or GRC systems (e.g., Jira, ServiceNow, AuditBoard).
• Proficiency in G-Suite and Slack.
• Bachelor's degree in a related field.
• Ability to work in a remote environment.

Pay

Lemonade's US base salary range for this full-time position is $115,000 - $135,000, plus equity and benefits. Salary varies by location and factors such as skills, experience, and education.

Benefits

• Comprehensive health and wellness coverage.
• Equity and 401(k) plan with employer match.
• 20 paid vacation days and parental leave.

Please note: We cannot sponsor work visas or consider applicants from Alaska, California, Colorado, Montana, Hawaii, New Mexico, and Puerto Rico.