Transactional Liability Claims Specialist

Overview

This Contract position involves managing a portfolio of complex Transactional Liability claims, including Representations & Warranties (R&W) Insurance and Tax Liability. The role requires strong legal and analytical skills to evaluate coverage, investigate alleged breaches of transaction-related representations and warranties, assess exposure, establish reserves, and negotiate claim resolutions.

Responsibilities

• Claim Investigation & Coverage Analysis

  • Investigate complex insurance claims involving alleged breaches of representations and warranties arising from mergers, acquisitions, and other corporate transactions.
  • Review and interpret insurance policies, purchase agreements, disclosure schedules, financial records, diligence materials, and other transaction documents.
  • Evaluate coverage issues, including breach, loss, retention, exclusions, valuation issues, and damages calculations.
  • Draft detailed coverage position letters, reservation of rights letters, information requests, and coverage determinations.

• Claim Evaluation & Financial Management

  • Assess liability and damages exposure through detailed review of financial, accounting, operational, and legal documentation.
  • Establish, monitor, and adjust claim reserves based on evolving exposure assessments.
  • Prepare coverage and reserve recommendations for management review.
  • Coordinate with outside counsel, forensic accountants, valuation professionals, and industry experts to evaluate complex claims.

• Resolution & Settlement

  • Develop and execute claim resolution strategies.
  • Negotiate settlement agreements, releases, and related documentation.
  • Monitor litigated matters when necessary, including oversight of outside counsel and litigation budgets.

Requirements

• Education: Juris Doctor (J.D.)
• Experience
  • Direct experience handling Representations & Warranties Insurance claims.
  • Experience representing buyers, sellers, private equity sponsors, insurers, or financial institutions in M&A transactions.
  • Prior experience evaluating complex damages and loss calculations.
  • Prior experience working with private equity, venture capital, or corporate transactional clients.
• Knowledge & Skills
  • Deep understanding of Transactional Liability and Representations & Warranties insurance products.
  • Strong knowledge of M&A transaction structures and corporate law principles.
  • Ability to identify and analyze nuanced coverage issues and legal arguments.
  • Advanced analytical, investigative, and critical-thinking skills.
  • Strong judgment in reserve setting and claim valuation.
  • Ability to effectively negotiate and influence outcomes in high-exposure matters.
  • Ability to manage a complex claim portfolio independently while meeting service expectations.

Preferred Qualifications

• Experience evaluating accounting principles, valuation methodologies, and financial statement analysis.

Compensation & Benefits

• Pay range: $130.00 - $150.00/hr
• Individual compensation offered within this range will depend on qualifications, skills, relevant experience, job knowledge, geographic location, internal equity, and other job-related factors.
• Eligibility requirements apply to some benefits and may depend on job classification and length of employment.
• Potential benefits for this temporary role may include:
  • Medical, dental & vision
  • Critical Illness, Accident, and Hospital
  • 401(k) Retirement Plan (Pre-tax and Roth post-tax contributions available)
  • Life Insurance (Voluntary Life & AD&D for the employee and dependents)
  • Short and long-term disability
  • Health Spending Account (HSA)
  • Transportation benefits
  • Employee Assistance Program
  • Time Off/Leave (PTO, Vacation or Sick Leave)

Location

• Chicago, IL (Contract position)
• Workplace type: Fully remote

Application Deadline

• Anticipated to close on Oct 30, 2026