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Executive Assistant
Chesapeake, VAMarch 30th, 2026
Executive AssistantWe're seeking a highly organized Executive Assistant with strong personal bookkeeping experience. This role supports the Owners directly by keeping their schedules, priorities, and personal financial details organized and running smoothly. If you're detail-oriented, proactive, and great at managing many moving parts, we want to hear from you.Key Responsibilities:Provide day-to-day administrative support, including managing calendars, preparing documents, coordinating appointments, and handling confidential information.Manage personal bookkeeping tasks for the Owners, including paying bills, tracking expenses, organizing receipts, reconciling accounts, and keeping personal financial records up to date.Assist with budgeting, personal expense reports, and maintaining accurate financial files.Coordinate with personal vendors and service providers as needed.Help keep projects and personal tasks on track by following up on deadlines and ensuring items are completed on time.Organize and maintain electronic and physical files for personal, legal, and financial matters.Communicate proactively with internal staff and outside contacts to help resolve issues and keep information flowing.Support with miscellaneous personal tasks, errands, and day-to-day needs (such as grabbing coffee, making reservations, or handling small personal projects).Qualifications:Minimum 5 years of experience as an Executive Assistant, Personal Assistant, Bookkeeper, or similar role.Experience managing personal bookkeeping, bill pay, and expense tracking for an individual or household.Strong organizational skills and the ability to handle multiple priorities with accuracy.Excellent communication and interpersonal skills.High level of discretion and professionalism when handling sensitive information.Proficient with Microsoft Office, accounting or budgeting tools, and cloud-based filing systems.
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