Insurance Coverage Associate/Senior Associate

CyberCoders; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

CyberCoders seeks an Insurance Coverage Associate or Senior Associate in Chicago to handle sophisticated first-party property and third-party liability matters, providing strategic coverage advice and influencing litigation strategy from inception through resolution.

You will work with insurer and policyholder clients, develop client relationships, mentor junior attorneys, and build a career in a specialized practice area in demand.

Qualifications

• J.D. from an accredited law school.
• Active bar admission and good standing in at least one U.S. jurisdiction.
• Strong legal research, writing, and analytical skills.
• Experience managing litigation matters and meeting competing deadlines.
• Ability to communicate complex legal concepts clearly and effectively to clients and colleagues.

Responsibilities

• Analyze insurance policies and claims to identify coverage issues, risks, and potential exposure.
• Draft coverage opinions, reservation of rights letters, denial letters, and other coverage-related communications.
• Advise clients on coverage positions, litigation risks, claim strategy, and resolution options.
• Manage and litigate insurance coverage disputes in state and federal courts.
• Draft pleadings, motions, discovery requests and responses, and appellate-quality briefs.
• Conduct legal research and analyze developments in insurance law.
• Collaborate with claims professionals, defense counsel, and experts to develop effective litigation and coverage strategies.
• Participate in depositions, mediations, hearings, arbitrations, and trial preparation.
• Handle matters involving first-party property coverage and third-party liability issues, including duty-to-defend and indemnity analyses.
• Mentor junior attorneys and legal staff (Senior Associate level).

Skills

J.D. degree

Bar admission

Legal research

Legal writing

Litigation management

Client counseling

Education

J.D. degree

Tools

Legal research databases

Job description

Insurance Coverage Associate / Senior Associate

Complex Coverage Litigation | Direct Client Contact | Growth Opportunity

Are you an attorney who enjoys the intellectual challenge of insurance coverage law and wants to work on sophisticated coverage matters rather than high-volume case handling?

We are seeking an Insurance Coverage Associate or Senior Associate to join a growing and highly regarded insurance practice. This role offers the opportunity to work directly with insurer and policyholder clients on complex first-party property and third-party liability coverage matters, provide strategic coverage advice, and play a meaningful role in litigation strategy from inception through resolution.

You’ll work alongside experienced coverage attorneys while taking ownership of significant matters, developing client relationships, and building a long-term career in a specialized and highly sought-after area of law.

Why Join Us?

• Handle sophisticated insurance coverage matters with substantial legal analysis and strategic responsibility.
• Work directly with clients, claims professionals, and litigation teams.
• Gain meaningful courtroom and litigation experience.
• Collaborate with attorneys recognized for their coverage expertise.
• Build specialized knowledge in a practice area that remains consistently in demand.
• Opportunities for mentorship, business development, and advancement.

What You'll Do

As a member of our coverage team, you will:

• Analyze insurance policies and claims to identify coverage issues, risks, and potential exposure.
• Draft coverage opinions, reservation of rights letters, denial letters, and other coverage-related communications.
• Advise clients on coverage positions, litigation risks, claim strategy, and resolution options.
• Manage and litigate insurance coverage disputes in state and federal courts.
• Draft pleadings, motions, discovery requests and responses, and appellate-quality briefs.
• Conduct legal research and analyze developments in insurance law.
• Collaborate with claims professionals, defense counsel, and experts to develop effective litigation and coverage strategies.
• Participate in depositions, mediations, hearings, arbitrations, and trial preparation.
• Handle matters involving first-party property coverage and third-party liability issues, including duty-to-defend and indemnity analyses.
• Mentor junior attorneys and legal staff (Senior Associate level).

What We're Looking For

Required Qualifications

• J.D. from an accredited law school.
• Active bar admission and good standing in at least one U.S. jurisdiction.
• Strong legal research, writing, and analytical skills.
• Experience managing litigation matters and meeting competing deadlines.
• Ability to communicate complex legal concepts clearly and effectively to clients and colleagues.

Preferred Experience

Associate Level

• 4+ years of insurance coverage, insurance defense, or related litigation experience.

Senior Associate Level

• 6+ years of insurance coverage and coverage litigation experience.
• Experience independently handling complex coverage disputes and client counseling.

Ideal Experience Includes

• Insurance coverage analysis.
• First-party property coverage matters.
• Third-party liability coverage disputes.
• Coverage opinions and position letters.
• Reservation of rights and denial letters.
• Declaratory judgment actions.
• Duty to defend and indemnity analyses.
• Commercial General Liability (CGL) coverage.
• Property and casualty insurance coverage litigation.
• Motion practice, depositions, and mediation experience.

The Ideal Candidate

The successful candidate is intellectually curious, client-focused, and enjoys tackling complex policy interpretation issues. They are comfortable serving as a trusted advisor, developing creative legal strategies, and balancing litigation objectives with business realities.

Whether you're an attorney looking to deepen your insurance coverage practice or a seasoned coverage lawyer seeking greater responsibility and career growth, we'd welcome the opportunity to connect with you.