Senior Underwriting Assistant – Chicago

Company Description

Cross Cover Insurance Services is a Managing General Underwriter (MGU) specializing in commercial property insurance, providing high-limit capacity and innovative solutions to our broker partners. As we continue to grow, we are seeking an experienced and motivated Senior Underwriting Assistant to join our team. This position is based in Chicago and offers the opportunity to play a key role in supporting our underwriting operations.

The Senior Underwriting Assistant is responsible for providing advanced underwriting support to the underwriting team throughout the policy lifecycle. This role requires a strong understanding of commercial property insurance, exceptional organizational skills, and the ability to manage a high-volume workload while maintaining accuracy and efficiency. The Senior Underwriting Assistant is expected to assist with training and mentoring less experienced team members and serve as a resource for underwriting support and operational best practices.

• Review and clear incoming submissions, ensuring all required information has been received before assigning to Underwriters.
• Prepare and organize account files for underwriting review and quoting.
• Generate and issue binders, policies, endorsements, cancellations, reinstatements, and other policy documentation.
• Order inspections and monitor completion, following up with vendors and brokers as needed.
• Communicate directly with brokers regarding outstanding underwriting requirements and policy documentation.
• Review files for accuracy and completeness prior to issuance.
• Assist Underwriters with policy servicing, renewals, endorsements, and account maintenance.
• Help train and mentor Underwriting Assistants on company procedures, systems, and best practices.
• Identify opportunities to improve workflows and operational efficiencies.
• Perform other duties as assigned by management.

• Minimum of 2–3 years of commercial property underwriting support or underwriting assistant experience required.
• High School Diploma required;
  Bachelor's Degree preferred.
• Prior experience working for an MGU, MGA, wholesaler, or commercial insurance carrier is preferred.
• Strong knowledge of commercial property insurance terminology, underwriting processes, and policy documentation.
• Proficiency in Microsoft Office, including Excel, Word, and Outlook.
• Excellent organizational and time management skills with the ability to prioritize multiple deadlines.
• Strong attention to detail and commitment to accuracy.
• Excellent written and verbal communication skills.
• Ability to work independently while collaborating effectively within a team environment.

• Commercial Property Insurance Knowledge
• Organization and Time Management
• Attention to Detail
• Communication Skills
• Problem Solving
• Accountability
• Collaboration
• Adaptability
• Process Improvement
• Leadership and Mentorship

The above is intended to describe the general content of and requirements for the performance of this position. It is not to be construed as an exhaustive statement of duties, responsibilities, or required skills and capabilities. Nothing in this job description restricts management's right to modify, expand, assign, or reassign duties and responsibilities relating to this position at any time. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the position.

• Medical, dental, and vision insurance
• Company-sponsored life and disability insurance
• Paid time off and company holidays
• 401(k) retirement plan with company match
• Opportunities for professional development and career growth

Insurance

Full-time