Executive Assistant / Personal Assistant

A real estate investment and management firm in Skokie is seeking a highly organized and discreet Executive and Personal Assistant to provide executive and personal support to the principal and his family. This is a fully onsite, hands-on position with broad responsibility and visibility, offering a competitive salary range of $100,000 - $130,000 and ideal for someone who enjoys variety and takes pride in anticipating needs and managing competing priorities. Working closely with the principal, his family, and departments across the company, the Executive and Personal Assistant will support scheduling, business and personal travel, financial administration, charitable requests, and various executive and family-related projects. A comprehensive benefits package is offered, including but not limited to health insurance, a 401(k) match, generous PTO, and access to an office gym and kitchen stocked with snacks and drinks.Responsibilities of the Executive and Personal Assistant:Oversee the principal’s calendar, prioritize scheduling requests from direct reports, and adjust appointments as business needs change.Organize meetings, prepare necessary documentation, manage correspondence, and research and compile information as requested.Arrange business and family travel, including transportation, itineraries, reservations, appointments, and required personal documents.Keep administrative records and files up to date, monitor outstanding tasks and deadlines, coordinate follow-ups, and resolve day-to-day issues.Facilitate approved personal and business payments, including checks, transfers, and wire transactions, while coordinating charitable contributions and maintaining related records.Monitor monthly credit card statements, collect and organize receipts, resolve discrepancies with the finance team, and compile information for the principal’s semiannual personal financial statement.Coordinate special assignments, work with in-house attorneys on applications and related documentation, and proactively address the principal’s and family’s needs while maintaining strict confidentiality.Qualifications of the Executive and Personal Assistant:At least five years of experience providing executive or personal support to a senior-level leader.Proven ability to stay organized, balance multiple priorities, and ensure responsibilities are completed accurately and on time.Sound judgment, discretion, adaptability, and a consistently professional and positive demeanor.Excellent written and verbal communication skills, with the ability to resolve issues independently and effectively.Experience managing confidential records and handling sensitive personal, business, and financial information.Proficiency in Microsoft Outlook, Word, and Excel, along with the ability to adapt to new software and administrative tools.A self-motivated and solutions-oriented approach, with the ability to work independently, collaborate across teams, and anticipate needs before they arise.P-5