Transactional Liability Claims Specialist

Overview

This Contract position manages 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.
  • Partner 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 as needed, including oversight of outside counsel and litigation budgets.

Requirements

• Education: Juris Doctor (J.D.) degree.
• Direct experience handling Representations & Warranties Insurance claims.
• Experience representing buyers, sellers, private equity sponsors, insurers, or financial institutions in M&A transactions.
• Familiarity with accounting principles, valuation methodologies, and financial statement analysis.
• Experience evaluating complex damages and loss calculations.
• Prior experience working with private equity, venture capital, or corporate transactional clients.
• 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 complex damages and loss calculations.
• Prior experience working with private equity, venture capital, or corporate transactional clients.

Compensation & Benefits

• Pay range: $130.00 - $150.00/hr.
• Individual compensation offered within this range depends 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. Benefits 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 & Workplace Type

• Contract position based out of Chicago, IL
• Fully remote

Application Information

• Anticipated application close date: Oct 28, 2026

Additional Notices

• San Francisco Fair Chance Ordinance: For positions located in San Francisco, the organization will consider qualified applicants with arrest and conviction records.
• Massachusetts Lie Detector: Unlawful to require or administer a lie detector test as a condition of employment or continued employment.
• Use of Artificial Intelligence (AI): AI may be used to support parts of the hiring process (including sourcing, screening, and evaluating candidates). Final decisions are made by the hiring team.