Remote Compliance Manager – AI-Driven Issue & Risk

Lemonade; United States; On-site; USD 115,000 - 135,000; Full time

Job summary

Lemonade is seeking a Compliance Manager to lead a best‑in‑class issues program across our growing insurance portfolio. You’ll own the lifecycle from identification to remediation and reporting, collaborating with Operations, Claims, and Product to manage regulatory risk as we scale.

You’ll apply AI and automation to track, analyze, and improve issue handling, driving smarter, faster decisions and strong governance across the business.

Qualifications

• 7+ years of regulatory or compliance experience in US personal lines insurance, with a strong focus on issue management and risk mitigation.
• Deep 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.

Responsibilities

• 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

Skills

Regulatory compliance

Issue management

Data-driven decisions

AI/automation in compliance

Cross-functional collaboration

Regulatory risk analysis

Education

Bachelor's degree in related field

Tools

Jira

ServiceNow

AuditBoard

G-Suite

Slack

Job description

Lemonade is seeking a Compliance Manager to lead a best‑in‑class issues program across our growing insurance portfolio. You’ll own the lifecycle from identification to remediation and reporting, collaborating with Operations, Claims, and Product to manage regulatory risk as we scale.

You’ll apply AI and automation to track, analyze, and improve issue handling, driving smarter, faster decisions and strong governance across the business.