Root was founded on the belief that car insurance is broken, and we set out to change it. We’re harnessing the power of technology to revolutionize this archaic, complicated industry. Using machine learning and mobile telematic platforms, we’ve built one of the most innovative insurtech companies in the world.

The Opportunity

We are looking for a Senior Complex Litigation Attorney, reporting to the Claims Legal Managing Attorney, and is responsible for managing a docket of complex pre-litigation and litigated matters, working in coordination with an adjuster and outside counsel. The role functions as a central escalation and decision-making resource for matters involving heightened exposure, including excess judgment risk, bad faith allegations, and significant financial, regulatory, or reputational concerns. The position will provide legal advice on risk identification, escalation and mitigation by evaluating resolution strategy and facilitating escalation to the Office of General Counsel in accordance with established escalation guidelines and authority levels.

This position will also provide support to the Office of General Counsel on pre-litigated and litigated complex matters and will function as a key interface between Claims, Claims Legal, Litigation leadership, House Counsel, and OGC. This role offers challenging and rewarding opportunities to influence enterprise risk outcomes, drive consistency in escalation and mitigation practices, and help build and lead the Complex Claims Litigation Team.

Salary Range:  $140,000 - $160,000

Root is a “work where it works best” company. This means we will support you working in whatever location that works best for you across the US.

How You Will Make an Impact

• Support Claims business partners by providing legal advice and leadership with respect to early identification, evaluation, and mitigation of complex litigation, excess exposure, and bad faith risk.
• Serve as a primary escalation point for complex pre-suit and litigated claims, including matters involving disputed or time-limited demands, rejected policy limits, evolving injuries, sophisticated plaintiff’s counsel, or allegations of mishandled claim handling.
• Execute and own escalation decisions for complex litigation matters.
• Provide timely legal risk assessments and resolution recommendations; The role will also provide escalation and resolution notifications to the Office of General Counsel using appropriate attorney-client privilege protocols.
• Analyze complex legal and factual issues and conduct extensive, well-reasoned legal research to support litigation strategy, settlement decisions, and enterprise risk mitigation.
• Develop and advise on defense and resolution strategies for complex property and casualty matters in both pre-suit and litigated phases, including trial readiness and settlement posture.
• Work closely with the Claims Department, Litigation leadership, and House Counsel to ensure legal compliance, consistent escalation, and effective mitigation of complex exposure.
• Participate in complex claim file reviews and provide training, guidance, and escalation of best practices to Claims and Litigation partners to reinforce early risk identification and escalation culture.
• Identify and escalate market-wide, regulatory, operational, or reputational risks arising from complex litigation, including policy form issues, product concerns, or systemic claim handling exposure.
• Provide oversight and direction for complex litigation file management activities and contribute to the development and maturation of the Complex Claims Litigation Team.
• Attend continuing legal education seminars to maintain a high level of professional expertise and stay current on legal trends impacting the insurance and claims environment.
• Integrate legal support staff into the complex case handling process and contribute to documentation, process alignment, and knowledge sharing initiatives.

What You Will Need to Succeed

• Minimum of 5–7 years of relevant legal experience handling complex claim litigation in the property and casualty insurance space or providing legal advice to that business.
• Demonstrated experience handling excess exposure and bad faith litigation matters internally for a property and casualty insurance carrier.
• Strong understanding of the insurance claims lifecycle, including pre-suit claim handling, litigation management, and escalation frameworks.
• Proven ability to assess litigation, excess, and bad faith risk and make sound judgment calls in high-exposure matters.
• Demonstrated track record of working effectively with claims professionals, litigation leaders, in-house counsel, and senior legal leadership to resolve complex claim matters.
• Demonstrated ability to build, maintain, and manage strong proactive professional relationships with outside counsel in all jurisdictions. 
• License to practice law in at least one state and in good standing.
• Demonstrated self-starter skills with the ability to manage competing priorities, exercise independent judgment, and operate effectively in high-risk, high-impact matters.
• Demonstrated ability to work collaboratively across teams of varying size and function.
• Ability to manage a high volume of complex matters while prioritizing based on exposure, urgency, and enterprise risk.
• Strong legal research, writing, and analytical skills, including experience with motion practice and settlement evaluation.
• First chair jury trial experience in complex litigation cases is preferred.
• Positive, collaborative mindset with strong verbal and written communication skills.
• Solid Google Office proficiency; experience with Westlaw is a plus.
• The position requires approximately 5% travel for on-site business meetings.

As part of Root's interview process, we kindly ask that all candidates be on camera for virtual interviews. This helps us create a more personal and engaging experience for both you and our interviewers. Being on camera is a standard requirement for our process and part of how we assess fit and communication style, so we do require it to move forward with any applicant's candidacy. If you have any concerns, feel free to let us know once you are contacted. We’re happy to talk it through.

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