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

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. The target compensation range for this Chicago based role is $61,000 to $80,000 and is based on the candidate experience level for the position. Key Responsibilities 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. 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.