Associate Attorney – Insurance Coverage

Role Description
We are seeking an Associate Attorney with at least 2 years of insurance analysis and coverage experience to join our Chicago, IL office. The ideal candidate will have a strong background in analyzing complex insurance policies and handling coverage-related disputes.

In this role, you will work with experienced coverage and litigation attorneys on matters involving insurance claims analysis, coverage disputes, and litigation for insurance company clients. The practice includes a wide range of industries and claims, including defective products, mass torts, environmental contamination, habitability, transportation, personal injury, professional liability, and intellectual property.

This position is hybrid in our Chicago office in Willis Tower.

What You’ll Do

• Handle all phases of insurance coverage analysis and related civil litigation in state and federal court.
• Draft coverage opinions, reservation of rights letters, and other coverage-related communications.
• Draft pleadings, motions, and discovery, and participating in depositions, mediations, and hearings.
• Provide strategic legal advice to insurance company clients and collaborate with claims professionals and adjusters.
• Monitor underlying litigation and evaluating exposure under applicable policies.
• Regularly interface with clients, opposing counsel, and attend court hearings and oral arguments, both remotely and in-person.

What We’re Looking For
We are looking for an attorney who is intellectually curious, detail-oriented, and interested in developing a strong insurance coverage and litigation practice. Successful candidates will also bring:

• Excellent research, writing, and verbal communication skills.
• A collaborative approach to working with partners, associates, paralegals, and law clerks.
• A diligent, proactive attitude and a genuine interest in learning.
• The ability to manage assignments independently, take ownership of work, and meet deadlines.

Qualifications

• Active bar license in Illinois
• Juris Doctor from an accredited law school
• At least 2 years of experience in insurance coverage and/or insurance defense litigation in either state or federal court.
• Excellent communication and interpersonal skills
• Exceptional writing, organizational, and advocacy skills
• Prior experience in billable-hour environment preferred

What Sets This Role Apart
This role offers the opportunity to build a sophisticated insurance coverage and litigation practice with the support of experienced attorneys who are invested in your development.

You will benefit from:

• Practical training in insurance coverage analysis, litigation strategy, drafting, client communication, and court appearances.
• Close mentorship from partners and senior attorneys who provide guidance, feedback and opportunities for professional growth.
• Early ownership of cases and substantive assignments with meaningful involvement in case strategy.
• Exposure to complex, high-stakes matters across a wide range of industries and claims.
• A collaborative team culture with accessible leadership and a clear path for long-term development and advancement.

Featured benefits

• Medical insurance
• Vision insurance
• Dental insurance
• 401(k) with Company Match
• Paid parental leave

Interview Process Timeline

Application

Our team will review your application. Please submit your resume and cover letter.

First Round Interview
Our Director of Recruiting will reach out to you to schedule a preliminary 30–45-minute virtual interview with the hiring manager(s).

Second Round Interview
Here you’ll meet some of the team who will evaluate your skillset and assess if you are a good culture fit for the firm. You will have the opportunity to tour our office and meet with the entire team in person.

Offer
Congratulations! If the hiring team thinks you’re a good match, we will extend an offer to join the firm.

About Life at Tressler

Tressler LLP is an award-winning law firm with ten offices located in six states - California, Illinois, Missouri, New Jersey, New York, and Pennsylvania. Trusted for 40 years, our firm has significant depth and experience in the resolution of disputes through mediation, arbitration, litigation, and trials.

The majority of Tressler attorneys devote their practice to the representation of the insurance industry in coverage analysis and resolution, litigation, underwriting consultation, product development, claims management, and reinsurance. In addition, Tressler attorneys represent clients in commercial litigation, defense litigation, corporate transactions, government law, employment law and litigation, intellectual property, and condominium and common interest community association law. Tressler has been named to the prestigious Best Lawyers “Best Law Firms” lists for the past six years. We are proud to be a Certified Great Place to Work© in the U.S.A., a ranking based on our employee happiness scores and positive reviews of our management team.