Administrative Assistant II, Executive Support, Data Reporting, Project Management

CNA Insurance

Administrative Assistant II at CNA providing high-quality administrative support within the Commercial Underwriting organization. Managing logistics, documentation, and collaboration for senior leadership.

Posted 5/16/2026full-timeChicago • Illinois, New York, Pennsylvania • 🇺🇸 United StatesMid-LevelSenior💰 $35,000 - $65,000 per yearWebsite

About the role

Key responsibilities & impact

Provide proactive administrative and logistical support that enables leaders to focus on strategic priorities
Manage complex calendars, meeting logistics, and scheduling; anticipate conflicts and resolve issues independently
Coordinate end-to-end travel arrangements and process expense reports accurately and on time
Draft, prepare, and distribute professional correspondence, reports, presentations, and meeting materials
Prepare large datasets, reports, and presentation materials for senior leadership and internal or external meetings
Maintain organized electronic files, SharePoint sites, and databases with strong version control and file hygiene
Handle sensitive and confidential information with a high level of discretion and professionalism
Provide timely and accurate support related to broker and agency activities, as applicable
Update and maintain business opportunities, relationships, and reporting in Salesforce and other internal systems
Partner with internal teams to support onboarding, changes, and agency needs
Gather data and prepare analyses, reports, and presentations to support business unit priorities
Serve as a reliable point of contact for leaders and internal partners, responding promptly and professionally
Apply sound judgment and initiative to identify solutions and escalate complex issues appropriately
Adapt effectively to changing priorities while maintaining a high standard of service and accuracy
Assist with special projects as needed, with quality, accuracy, and timely execution
Ensure final deliverables are complete, meet quality standards, and achieve intended outcomes
Coordinate meetings, events, and team activities as needed
May serve as a facilities and office liaison, including supply management, equipment coordination, and vendor support
Process invoices, accounts payable activities, and other operational requests as required.

Requirements

What you’ll need

Some college coursework preferred (Business, Accounting, Marketing, or related field)
Typically 4+ years of administrative experience, preferably supporting leaders or teams in a professional services or corporate environment
Strong written and verbal communication skills with professional judgment and tone
Excellent organizational skills with the ability to manage multiple priorities and deadlines
Strong interpersonal skills with the ability to collaborate effectively across levels and functions
Ability to work independently, anticipate needs, and resolve issues proactively
Intermediate proficiency in Microsoft 365 (Outlook, Teams, Word, PowerPoint, Excel); strong PowerPoint and Excel skills preferred
Experience using AI productivity tools (e.g., Copilot or similar) and comfort learning new technologies
Familiarity with data analysis or reporting tools (e.g., Power BI, Looker) is a plus.

Benefits

Comp & perks

Comprehensive and competitive benefits package
Health insurance
Retirement plans
Paid time off

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

data analysisreportingcalendar managementtravel arrangementsexpense reportingpresentation preparationfile managementinvoice processingaccounts payableproject coordination

Soft Skills

communicationorganizational skillsinterpersonal skillsproblem-solvinginitiativeadaptabilityprofessionalismdiscretioncollaborationjudgment