Senior Claims Counsel

Confidential; Chicago (IL); Hybrid; USD 110,000 - 160,000; Full time

Job summary

Confidential in Chicago, IL, seeks a Senior Claims/Litigation attorney to protect company interests across complex first- and third-party claims. Hybrid work arrangement with guidance from the Senior Director, Litigation, and collaboration across Legal, Compliance, and Operations teams.

You will analyze claims, oversee outside counsel, manage case files, negotiate settlements, and provide strategic risk assessments to leadership.

Qualifications

• J.D. from ABA-accredited law school and active state bar admission in good standing.
• Minimum of three years of experience handling insurance claims or litigation.
• Illinois bar admission preferred.
• Strong communication and analytical skills are essential.

Responsibilities

• Own the handling of complex first-party and third-party claims across general liability, pollution, and automobile insurance lines.
• Direct claim investigations, evaluate coverage, liability, and damages, and document resolution strategies.
• Consult with counsel to minimize costs and achieve cost-effective resolutions.
• Provide informed exposure assessments to claims leadership and senior management.
• Negotiate settlements with claimants and advise senior leadership on status and strategy.
• Appear in court proceedings, mediations, and settlements, with limited travel as needed.
• Direct outside counsel on litigation strategy and manage discovery efforts.

Skills

Clear communication

Attention to detail

Independent decision-making

Project management

Collaboration

Education

J.D. from ABA-accredited law school

Job description

This is a key position within the Legal department, located in Chicago, IL, with a hybrid work schedule. Under the direction of the Senior Director, Litigation, this role is tasked with protecting the interests of the company and ensuring that claims are handled properly for our customers, their customers, and our affiliates. Duties include, but are not limited to, analyzing claims, conducting investigations, overseeing outside litigation counsel, engaging in high-level problem solving, negotiation, and legal analysis, organizing and managing case files, effectuating risk transfer, and carrying out special projects for the legal department.

Responsibilities

• Own the handling of complex first-party and third-party claims across general liability, pollution, and automobile insurance lines.
• Direct claim investigations, evaluate coverage, liability, and damages, determine ability to tender claims to subcontractors, and develop and document clear resolution strategies.
• Consult with counsel regarding strategy to minimize costs and achieve cost-effective resolutions.
• Provide well-reasoned exposure assessments to claims leadership and senior management.
• Work closely with internal and external stakeholders, including those in the Legal, Compliance, and Operations departments, as well as our customers, to ensure that all relevant information has been collected and to provide feedback to such parties for operational improvement.
• Negotiate settlements directly with claimants and advise senior leadership as to the status of these negotiations.
• Appear as company representative in court proceedings, mediations, settlement conferences, and trial, as applicable. Limited travel to these proceedings may be required.
• Direct outside counsel on litigation strategy through the course of claim administration and litigation.
• Manage discovery efforts and planning and preparation of witnesses and materials.
• Help oversee the claims process and ensure all claims data and information is appropriately entered into relevant systems/databases, and follow up on all previously tendered claims to determine outcome.
• Advise on tenders, additional insured issues, contractual indemnity, contribution, subrogation, and allocation among carriers.
• Respond to various internal and external stakeholder questions regarding claims, litigation, and other related legal issues.
• Provide advice, guidance, and representation on suits brought by or threatened against Lessen by any affiliate, customer, third party, or insurer.
• Identify claim trends and recurring issues.
• Perform ad hoc projects and other duties, as assigned.

Professional Skills

• Ability to communicate directly and effectively with claims professionals, executives, outside counsel, and business teams.
• Ability to take ownership of claims by identifying missing facts, developing strategy, providing recommendations, and driving matters through resolution.
• Demonstrated attention to detail and ability to catch inconsistencies in claims files, pleadings, and correspondence.
• Ability to independently identify bad‑faith and extra-contractual risks and know when an issue requires escalation.
• Comfort making decisions in a fast-moving environment where the facts may be incomplete and the law may vary materially by jurisdiction.
• Ability to proactively address issues and take initiative to achieve ideal outcomes.
• Ability to manage and prioritize multiple projects simultaneously.
• Strong interpersonal and collaborative skills.
• Independent decision‑making skills and sound judgment.

Qualifications

• J.D. from an ABA-accredited law school required and are an active member in good standing of at lease one U.S. state bar (preferably Illinois)
• At least three years of experience in handling insurance claims or litigation at a law firm, insurance carrier, TPA, or comparable organization.

About the Company

We are a rapidly growing, technology-enabled property services organization transforming how residential and commercial properties are maintained and managed across the United States.

By combining innovative technology, data-driven solutions, and an extensive network of service professionals, we help some of the nation's leading property owners, operators, and businesses streamline maintenance operations, improve service delivery, and drive operational efficiencies.

Our platform connects clients with a nationwide network of qualified service providers, allowing us to deliver scalable, reliable solutions across diverse property portfolios. We operate at the intersection of technology, real estate, and facilities management, with a strong focus on innovation, operational excellence, and delivering exceptional experiences for our clients and partners. As we continue to evolve and expand, we are focused on building high-performing teams that thrive in a collaborative, fast-paced environment and are motivated by the opportunity to make a meaningful impact.