Commission High Risk Civilian Contractor Jobs in Chicago, IL

8750 W Bryn Mawr Ave #500, Chicago, IL 60631, USA

Posted Tuesday, August 4, 2026 at 6:00 AM

Power Construction is consistently regarded as one of Chicago's largest and most respected General Contractors according to Crain's Chicago. But beyond that, you can find us on the golf course, brewing beer, attending neighborhood festivals, giving back to the community, and spending time together during a range of company-sponsored events. Our culture is one of the reasons we've been selected by our employees as a top workplace year after year and it's reflected in our current 91% employee retention rate.

We are builders. We crave being in the field and share an appetite for innovation. We believe that bringing diverse perspectives together helps foster stronger outcomes. We are driven to wow our clients and business partners, improve our processes, hire the right people, and help them grow.

The Director of Risk Management is responsible for the strategic oversight and execution of the Company's insurance, claims, and risk management programs. This position provides enterprise-level leadership across construction operations, contractual risk transfer, insurance placement, claims management, and controlled insurance programs (CCIP/OCIP/SDI). The Director serves as a trusted advisor to executive leadership, operations, and project teams, ensuring the Company's risk profile is proactively managed, financially optimized, and aligned with long-term business objectives. The Director owns program design, renewals, and claims management while partnering with Operations, Safety, Legal, Finance, outside counsels and brokers to drive consistent risk decisions across the business.

• Partners with the VP of Risk direct departmental strategy, mentoring high-performing teams and scaling risk service offerings to support evolving business operations.
• Optimizes the company's total cost of risk (TCOR) by strategically structuring insurance program coverages, limits, and deductibles.
• Directs the Company's casualty insurance strategy, leading annual renewals and broker partnerships to secure optimal market placement, pricing, and coverage terms.
• Directs the comprehensive corporate insurance portfolio including WC, GL, Auto, Umbrella/Excess, Professional, Cyber, and SDI ensuring program structures evolve alongside the Company's expansion.
• Directs the claims management (investigation, reserving, litigation, resolution) and lead quarterly reviews and develop action plans to reduce severity and protect outcomes.
• Govern CCIP/OCIP performance (enrollment, compliance, loss results) and partnering with Operations and Safety.
• Oversee subcontractor insurance compliance and onboarding and train PM/field teams on requirements to strengthen contractual risk transfer.
• Negotiates complex contractual risk terms—including indemnity, insurance, and liability caps to limit corporate financial exposure.
• Support the subcontractor prequalification framework, driving consistent enforcement of compliance policies and risk thresholds across all subcontract awards.

• Required: Bachelor’s degree. Preferred: Risk Management, Insurance, Finance, Construction Management, or related field.
• Required: CRIS designation (or equivalent risk/insurance credential). Preferred: ARM, CPCU, or similar advanced designation.
• Required: 10+ years progressive construction risk/insurance experience with direct ownership of insurance placement/renewals, claims governance, contractual risk transfer, and controlled insurance programs (CCIP/OCIP).
• Proven people leadership and executive-level communication, that drives strategic alignment and collaboration among diverse internal stakeholders (Operations, Safety, Legal, Finance) and major external partners.

• Translates complex loss trends, premium data, and operational metrics into actionable executive recommendations and high-impact risk management directives.
• Directs the end-to-end placement and claims lifecycle for all primary lines (WC/GL/Auto/Professional), utilizing specialized construction sector knowledge to protect corporate assets.
• Conveys complex risk and insurance concepts through concise, executive-level messaging that facilitates fast, informed decision-making.
• Builds partnership across the organization to execute process improvements and secure cross-functional alignment.
• Exercises the ability to influence and negotiate effectively with brokers, carriers, and internal partners to reach equitable outcomes.
• Drafts key contract clauses to balance risk, secure necessary insurance, and limit legal exposure.

Salary Range: $150,000 - $175,000

Compensation for this role includes a base salary plus an annual discretionary bonus. Details on our benefits can be found on the Benefits tab within the Careers section of the website.

Power Construction is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression, veteran status, or any other status protected under federal, state, or local law. Power Construction is committed to increasing opportunities for historically disadvantaged workers (including women and members of disproportionately affected racial and ethnic groups), as well as residents of marginalized communities.

8750 W Bryn Mawr Ave #500, Chicago, IL 60631, USA