Director, Risk Management

Pepper Construction Group; Barrington (IL); On-site; USD 170,000 - 210,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401k match

Paid time off

Parental leave

Job summary

Pepper Construction seeks a seasoned Risk & Insurance Leader to direct contractor insurance programs, CCIP and allied risk controls across our regions. You will design and manage programs with brokers and insurers, ensuring optimal coverage, cost allocation, and risk transfer for complex projects.

The role requires 10+ years of risk management experience, strong leadership, and the ability to influence across operations, legal, and executive teams.

Qualifications

• Bachelor’s degree required; master’s preferred.
• Professional designations CRMP, CIC, ARM or CRM highly regarded.
• Minimum 10 years of progressive risk and insurance leadership experience.
• Experience in construction or real estate risk management is preferred.
• Strong leadership and ability to influence executive teams.

Responsibilities

• Lead CCIP and Subcontractor Default Insurance program governance and improvement.
• Design, place and manage insurance programs with brokers, underwriters and insurers.
• Review coverages, limits, deductibles and structures for alignment with growth and project risk.
• Develop insurance cost allocation and billing models for pricing.
• Negotiate terms with clients, subcontractors and consultants to mitigate risk.
• Oversee claims strategy, data integrity, and reporting to executives.

Skills

Risk management

Leadership

Stakeholder comms

Contract & risk analysis

Education

Bachelor's degree in Business/ Risk Management

CRMP/CIC/ARM/CRM

Tools

CCIP

Claims management

Job description

With offices in Illinois, Wisconsin, Indiana, and Ohio, Pepper Construction is a national general contracting and construction management firm that primarily serves the private sector. Pepper Construction provides clients the experience and resources of a national company, combined with the hands‑on approach of a local company.

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.
• Reviews contractual insurance and risk allocation provisions; identifies and advises on one‑sided, unusual, or high‑risk 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
• 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 risk‑related decision making
• 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 construction‑focused insurance/bonding brokerage or insurance carrier environment
• Demonstrated technical experience managing complex insurance and risk control programs, and large‑scale 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.

Pepper Construction is an Equal Employment Opportunity employer.

Please note: Pepper does not sponsor work visas.