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

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. JOB DESCRIPTION: Administrative Assistant II Location: Chicago CNA Office Hybrid work: 3 days in office with possibility of more days on-site, if needed Position Summary We are seeking an experienced Administrative Assistant II to provide proactive, high-quality administrative and operational support to leaders within our Commercial Underwriting organization. This role helps leaders operate efficiently by managing complex logistics, preparing data-driven materials, and serving as a trusted partner across teams. The ideal candidate is highly organized, detail‑oriented, adaptable, and comfortable working in a fast‑paced, collaborative environment while handling sensitive and confidential information with discretion. Qualified candidates should have intermediate skills in the Microsoft Office Suite, including PowerPoint and Excel, plus experience using AI tools (such as Copilot or similar). Familiarity with data analysis and reporting tools (such as Looker and Power BI) is helpful, along with the ability to thrive in an agile learning environment. Key Responsibilities Administrative & Executive Support 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. Business & Broker Support 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. Customer Service & Partnership 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. Office & Project Support 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. Qualifications Education & Experience 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. Skills & Capabilities 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. #LI-MA1 #LI-Hybrid In certain jurisdictions, CNA is legally required to include a reasonable estimate of the compensation for this role. In District of Columbia, California, Colorado, Connecticut, Illinois, Maryland, Massachusetts, New York and Washington, the national base pay range for this job level is $35,000 to $65,000 annually. Salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location. CNA offers a comprehensive and competitive benefits package to help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals. For a detailed look at CNA’s benefits, please visit cnabenefits.com. CNA utilizes AI-enabled technology during the recruiting process. For more information, please visit our careers page. CNA is committed to providing reasonable accommodations to qualified individuals with disabilities in the recruitment process. To request an accommodation, please contact View email address on click.appcast.io At CNA, we are focused on success, individually and collectively. We pride ourselves on promoting a culture that challenges and engages people. We strive to connect people, departments and business areas, to function as a team, and to serve our customers and communities with professionalism and respect. Our dedication to employee engagement, continuous learning and the open exchange of ideas is the cornerstone of our business. These ideals, combined with our focus on the customer, enable us to explore new market opportunities and build on our success. Our values, culture and financial strength are what differentiates us from other employers and make CNA the place you want to work. At CNA, we are committed to advancing a culture of inclusion – one that attracts talent from all walks of life, fosters respect and collaboration, and enables all of our colleagues to do their best work. At CNA, we have a long standing commitment to the diverse communities in which we live and work. We actively make a difference for the greater good through partnerships, sustainability, initiatives, and working together for a better tomorrow. Corporate Social Responsibility is not one person, or one department, it's the entire enterprise coming together to make the world a better place.