Director, Risk Management

Pepper Construction•Barrington, IL

4d•Remote

About The Position

Pepper Construction is a national general contracting and construction management firm serving primarily private-sector clients, with offices in Illinois, Wisconsin, Indiana, and Ohio. The Director, Corporate Risk Management will lead the Company’s enterprise risk management strategy as the business grows beyond $3 billion in revenue. The role provides strategic oversight of insurance programs, claims management, contractual risk, loss control, and risk mitigation initiatives across the organization. The Director designs, places, and manages property and casualty insurance programs; supports Contractor Controlled Insurance Programs (CCIPs); and develops practical solutions to protect the Company’s people, projects, assets, and financial performance. As a trusted advisor to executive leadership, business unit leaders, and cross-functional partners, the Director embeds risk awareness in daily operations, enables informed decision-making, and supports continued growth. The role calls for technical expertise, sound judgment, collaborative influence, and an innovative approach to managing risks in a complex construction environment.

Requirements

Bachelor’s degree from an accredited university in Business Administration, Business Management, Risk Management, Insurance, Risk Control, or a related field.
Experience leading implementation, governance, and continuous improvement of a Contractor Controlled Insurance Program (CCIP) and Subcontractor Default Insurance program.
Professional designation such as Certified Risk Management Professional (CRMP), Certified Insurance Counselor (CIC), Associate in Risk Management (ARM), or Certified Risk Manager (CRM).
At least 10 years of progressive risk and insurance management experience.
Technical experience managing complex insurance and risk-control programs and large-scale claims portfolios.
Previous experience providing leadership and direction to a team of risk management and claims management professionals.
Strong leadership presence and ability to advise and influence operational, legal, and executive management teams.
Excellent written, verbal, and presentation skills.

Nice To Haves

Master’s degree.
Experience in the construction or investment real estate industry, or in a construction-focused insurance or bonding brokerage or insurance carrier environment.

Responsibilities

Lead implementation, governance, and continuous improvement of the Contractor Controlled Insurance Program (CCIP) and Subcontractor Default Insurance program.
Design, place, and manage insurance programs with brokers, underwriters, and insurers to allocate, mitigate, and finance risk.
Review insurance coverage, limits, deductibles, and structures for alignment with business growth, project risk profiles, coverage optimization, and market conditions.
Develop insurance cost-allocation and billing models for accurate divisional and project pricing.
Negotiate contractual insurance and bonding terms with clients, subcontractors, and consultants to mitigate retained risks.
Review contractual insurance and risk-allocation provisions and advise on one-sided, unusual, or high-risk terms.
Partner with the Corporate Legal Team to develop and negotiate risk-, insurance-, and bonding-related contract terms, exceptions, and amendments.
Obtain and evaluate specialty insurance coverage required by owner contracts or unique project risks.
Oversee claims strategy, valuation, and reserve adequacy in partnership with third-party claims administrators, adjusters, consultants, claims counsel, and the General Counsel.
Ensure claims data accuracy and provide actionable reporting to executive leadership.
Use claims trends to drive loss prevention and operational improvements.
Work with Operations, Safety, Fleet Management, Human Resources, Facilities Management, and project teams to implement systems, procedures, and controls that reduce loss frequency and severity.
Train and guide Operations project teams on insurance programs, CCIP requirements, risk controls, and risk management practices.
Advise operations leadership on risk-related decisions.
Oversee fleet risk strategy, including driver standards, insurance coverage, loss trends, auto liability exposure, and claims performance, in partnership with Safety and Operations.
Lead accident review, preventability determinations, repair estimate evaluation, severity tiering, and related cost-control processes.
Manage driver risk tracking, including point-assignment logic, scoring methodology, Samba MVR notifications, annual MVR reviews, and the system of record.
Lead the Fleet Safety Committee and provide governance, reporting, and escalation support for fleet risk decisions.
Analyze fleet loss frequency, severity, repeat drivers, and geographic trends to inform corrective actions, mitigation strategies, and reporting to executive leadership and insurance partners.
Ensure alignment with third-party administrators, carriers, and the overall claims management strategy for auto losses.
Develop and maintain relationships with brokers, carriers, third-party administrators, claims administrators, actuaries, loss-control specialists, and consultants.
Maintain insurance policies, certificates, and records, and report regularly on program performance, claims activity, and emerging risks.
Serve as an active member of the Corporate Enterprise Risk Committee reporting to executive management.
Represent and communicate the Company’s insurance and risk programs to internal stakeholders and external partners.
Provide leadership and direction to a support team of risk management and claims management professionals.