Ai Risk Analyst Jobs in Chicago, IL (NOW HIRING)

Company

Argo and Farm Family are specialty property and casualty insurance brands whose underwriting companies are wholly-owned subsidaries of Clearbrook Holdings Inc. Argo and Farm Family partner with agents and brokers to provide insurance solutions that enable businesses to manage risks with confidence.

Job Description

The Enterprise Risk Analyst supports the development, implementation, and continuous enhancement of the organization's Enterprise Risk Management (ERM) framework within a property and casualty insurance environment. This role is responsible for assisting in the identification, assessment, monitoring, and reporting of enterprise risks in alignment with regulatory expectations (e.g., NAIC ORSA), industry standards, and internal governance practices.

The Analyst partners cross-functionally with the various departments of Clearbrook Group to enhance risk visibility, strengthen control effectiveness, and support risk-informed decision making. This role contributes to both strategic and operational risk initiatives, with a focus on current and emerging risks impacting the organization.

We are open to considering candidates with a range of experience levels; the final level will be determined based on the candidate's qualifications, experience, and business needs. Compensation will be commensurate with experience and aligned to the level at which the candidate is hired.

This is a 100% in-office position. The role requires consistent on-site presence to support collaboration, real-time decision-making, and effective partnership with cross-functional teams.

KEY ACCOUNTABILITIES

Risk Identification & Assessment

• Support enterprise-wide risk identification and assessment processes, including Risk and Control Self-Assessments (RCSAs), risk registers, and emerging risk identification
• Evaluate inherent and residual risks across key categories, including insurance, operational, financial, and strategic risks
• Maintain and enhance risk taxonomies aligned with NAIC and COSO ERM frameworks
• Participate in cross-functional engagements to support risk identification, assessment, and monitoring activities
• Contribute to the design, implementation, and ongoing improvement of the ERM framework
• Support the Own Risk and Solvency Assessment (ORSA) process, including documentation, reporting, and governance alignment
• Maintain ERM policies, standards, and procedures to ensure regulatory compliance and audit readiness
• Support governance activities, including preparation of materials and documentation for risk committees and working groups
• Collect, aggregate, and analyze risk data arising from risk assessments and business processes
• Support development and refinement of key risk indicators (KRIs) and risk metrics
• Perform research and analysis to support enterprise risk initiatives and emerging risk evaluations
• Capture and track risk events, near misses, and loss data to support risk trend analysis
• Maintain risk registers, KRIs, and risk appetite metrics
• Prepare risk reporting for senior management, risk committees, and the Board
• Track risk issues, control gaps, and remediation activities to support timely resolution
• Maintain ERM dashboards and support ongoing reporting and analytics initiatives
• Support regulatory and rating agency reporting, including ad hoc requests
• Partner with first- and second-line functions to evaluate control design and operating effectiveness
• Support the development and maintenance of standardized control libraries aligned with SOX, MAR, and NAIC expectations
• Identify control gaps and recommend practical, risk-based mitigation strategies
• Support regulatory exam readiness and response activities (e.g., state Department of Insurance examinations)
• Ensure ERM documentation is accurate, current, and defensible
• Monitor regulatory developments and assess impacts to the ERM framework
• Engage with underwriting, claims, actuarial, finance, IT, and legal & compliance teams to embed risk management practices
• Support enterprise initiatives related to operational risk, third-party risk, model risk, AI risk, and IT risk
• Facilitate risk discussions, workshops, and training sessions as appropriate

QUALIFICATIONS

Required

• Bachelor's degree in risk management, finance, accounting, insurance, business, mathematics, or related field
• 2-5 years of experience in risk management, internal audit, compliance, or insurance operations
• Familiarity with insurance regulatory requirements, including NAIC guidance and ORSA

Preferred

• Experience within a Property & Casualty insurance organization
• Working knowledge of enterprise risk management frameworks (COSO ERM, ISO 31000)
• Exposure to SOX, Model Risk Management (SR 11-7), AI Risk Management (NIST AI RMF), or IT GRC frameworks
• Progress toward or completion of professional certifications (ARM, CRM, CERA, etc.)

KEY COMPETENCIES

• Strong analytical and critical thinking skills with attention to detail
• Ability to translate complex risk concepts into clear, actionable insights
• Effective written and verbal communication skills for senior audiences
• Collaborative mindset with strong relationship-building capabilities
• Strong organizational skills and ability to manage multiple priorities
• Results-oriented with a proactive approach to problem-solving
• Proficiency in Microsoft Office (Excel, PowerPoint, Word) and data analysis tools
• Ability to manage multiple priorities in a dynamic environment

The salary range provided reflects targeted hiring locations and will be commensurate with the candidate's experience, skills, and qualifications. Compensation may vary for candidates in other locations based on geographic differentials, cost of labor, and internal equity considerations.

• New York City, NY: $77,500.00 - $102,000.00
• Chicago, IL: $71,000.00 - $93,500.00
• All Other Geographic Locations: $65,000.00 - $85,000.00

Candidates must be legally authorized to work in the United States at the time of application. This role is not eligible for employer-sponsored work authorization now or in the future.

PLEASE NOTE:

Applicants must be legally authorized to work in the United States. At this time, we are not able to sponsor or assume sponsorship of employment visas.

If you have a disability under the Americans with Disabilities Act or similar state or local law and you wish to discuss potential reasonable accommodations related to applying for employment with us, please contact our Benefits Department at 210-321-8400.

Benefits and Compensation

We offer a competitive compensation package, performance-based incentives, and a comprehensive benefits program-including health, dental, vision, 401(k) with company match, paid time off, and professional development opportunities.

Core Values

At Clearbrook our Core Values are Integrity, Collaboration, Pursuit of Excellence and Forward Thinking. These values reflect who we are today and who we apsire to be - guiding how we work, how we lead and how we succeed.