Contractual Insurance Controller Jobs in Chicago, IL

The Director, Corporate Risk Management will lead the Company’s enterprise risk management strategy, providing strategic oversight of insurance programs, claims management, contractual risk, loss control, and risk mitigation initiatives across the organization. This role is responsible for designing, placing, and managing property and casualty insurance programs; supporting Contractor Controlled Insurance Programs (CCIPs); and developing practical solutions that protect the Company’s people, projects, assets, and financial performance.

Serving as a trusted advisor to executive leadership, business unit leaders, and cross-functional partners, the Director will help embed risk awareness into daily operations while enabling informed decision-making and supporting continued growth. The ideal leader brings strong technical expertise, sound judgment, collaborative influence, and an innovative approach to managing emerging business, operational, financial, and contractual risks within a complex construction environment.

MAJOR RESPONSIBILITIES

Risk Strategy & Insurance Programs

• Leads the implementation, governance and continuous improvement of a Contractor Controlled Insurance Program (CCIP) and Subcontractor Default Insurance program
• In collaboration with brokers, underwriters, and insurers, designs, places and manages insurance programs that effectively allocate, mitigate, and finance risk
• Regularly reviews insurance coverages, limits, deductibles, and structures to ensure alignment with business growth, coverage optimization, project risk profiles, and market conditions
• Develops insurance cost allocation and billing models to support accurate divisional and project pricing
• Meets with company clients, subcontractors, consultants to negotiate contractual insurance and bonding terms to mitigate retained risks.

Contractual & Financial Risk

• Reviews contractual insurance and risk allocation provisions; identifies and advises on one-sided, unusual, or highrisk terms
• Partners with the Corporate Legal Team to develop and negotiate contract terms, exceptions and amendments related to risk, insurance, and bonding
• Obtains and evaluates specialty insurance coverage required by owner contracts or unique project risks

Claims & Loss Management

• Partners with the third-party claims administrators (“TPAs”), claims adjusters/consultants, claims counsel, and General Counsel to oversee claims strategy, valuation, and reserve adequacy
• Ensures claims data accuracy and provides clear, actionable reporting to executive leadership
• Uses claims trends to drive loss prevention and operational improvements

Operational Risk & Loss Control

• Works closely with Operations, Safety, Fleet Management, Human Resources, Facilities Management, and project teams to implement systems, procedures and controls that reduce the frequency and severity of losses
• Provides training and guidance to Operation’s project teams on insurance programs, CCIP requirements, risk controls, and risk management best practices
• Serves as a trusted advisor to operations leadership on riskrelated decision making

Fleet Risk Management

• Oversees fleet risk strategy, including driver standards, insurance coverage, loss trends, auto liability exposure, and claims performance in partnership with Safety and Operations
• Leads accident review, preventability determinations, repair estimate evaluation, severity tiering, and related cost-control processes
• Manages driver risk tracking, including point assignment logic, scoring methodology, Samba MVR notifications, annual MVR reviews, and the system of record
• Leads the Fleet Safety Committee and provides governance, reporting, and escalation support for fleet risk decisions
• Analyzes frequency, severity, repeat drivers, and geographic trends to inform corrective actions, risk mitigation strategies, and reporting to executive leadership and insurance partners
• Ensures alignment with TPAs, carriers, and the overall claims management strategy for auto losses
•  

Management of External Partnerships & Provider Relations

• Develops and maintains strong relationships with insurance brokers, carriers, TPAs, claims administrators, actuaries, loss control specialists, and consultants
• Maintains all insurance policies, certificates, and records; provides regular reporting on program performance, claims activity and emerging risks
• Serves as an active member of the Corporate Enterprise Risk Committee reporting to executive management
• Represents and communicates the Company’s insurance and risk programs to internal stakeholders and external partners

POSITION REQUIREMENTS

• Bachelor’s degree from an accredited university in Business Administration, Business Management, Risk Management, Insurance, Risk Control, or a related field. Master’s Degree preferred
• Professional Designations: Certified Risk Management Professional (CRMP), Certified Insurance Counselor (CIC), Associate in Risk Management (ARM), or Certified Risk Manager (CRM)
• Minimum of 10 years of progressive risk and insurance management experience, preferably within the construction or investment real estate industry or a constructionfocused insurance/bonding brokerage or insurance carrier environment
• Demonstrated technical experience managing complex insurance and risk control programs, and largescale claims portfolios
• Previous experience successfully providing leadership and direction to a support team of risk management and claims management professionals
• Strong leadership presence with the ability to advise and influence operational, legal, and executive management teams
• Excellent written, verbal and presentation skills

The annual salary midpoint for this role is $195,000. We consider many factors when determining the actual hiring salary. These factors may include location, transferable skills, work experience, licensure and certification, business needs, internal equity, and market demands.

Pepper Construction is dedicated to offering our employees a comprehensive and best-in-class benefits package that prioritizes their physical, financial, and emotional well-being. We offer medical, dental, vision, life, and disability insurance plans, a generous 401k match, and a student loan repayment benefit. In addition to paid time off for company holidays, vacation, and personal days, Pepper offers fully paid medical and parental leave, mental health services, and more.

For additional information, visit www.pepperconstruction.com.