Executive Assistant to a Multi-Business Owner

About The Role This is not a traditional executive assistant role. The right candidate will serve as the right hand to a high‑volume entrepreneur who oversees multiple active businesses across the healthcare transportation, real estate, equestrian, and home improvement industries. You will work directly for the owner — not for any single company — and will be responsible for keeping all business operations running smoothly so the owner can focus on high-level growth and strategic development. This role demands exceptional organizational skills, sound judgment, and the ability to operate with a high degree of autonomy and discretion. The ideal candidate thrives in a fast‑paced, ever‑changing environment, takes initiative, and takes pride in solving problems before they escape. Business Portfolio You Will Support Trans Unit Medical Transportation – Non‑emergency medical transportation company based in Moorestown, NJ (partial ownership). Primary growth focus for the owner. VIP Medical Transport – Medical transportation operations based in Philadelphia, PA. Freedom Acres – Horse farm and equestrian operation located in Morristown, NJ, including horse racing activities. Chaouch Properties and Sons – Real estate investment and property management company, including apartment rentals and property flipping. Garden State Windows – Residential and commercial windows installation business serving New Jersey. Key Responsibilities Administrative & Correspondence Management Sort, open, prioritize, and respond to all physical mail across businesses. Manage and organize email inboxes – draft responses, flag urgent items, file and archive. Prepare and send business correspondence including letters, notices, and formal communications. Maintain organized filing systems (physical and digital) for all entities. Document & Contract Management Draft, prepare, and manage lease agreements for rental properties. Prepare contracts, vendor agreements, and business documents as needed. Track lease renewals, expirations, and key contract milestones. Maintain confidential records for all business entities with accuracy. Financial & Business Operations Support Assist with accounts payable/receivable tracking, invoice processing, and payment follow‑up. Liaise with accountants, attorneys, lenders, and financial advisors on behalf of the owner. Track expenses and maintain organized records for multiple business entities. Assist in preparing financial summaries and business reports as requested. Scheduling & Project Coordination Manage the owner's calendar across all businesses – schedule meetings, calls, and appointments. Coordinate with vendors, contractors, tenants, drivers, and business partners. Track project timelines and follow up on outstanding action items. Prepare agendas, meeting notes, and action item summaries. Growth & Development Support (Trans Unit Priority) Support the owner's strategic growth initiatives for Trans Unit Medical Transportation. Research potential business opportunities, partnerships, and expansion strategies. Prepare presentations, proposals, and materials to support business development. Track KPIs and operational metrics as directed. Personal & Miscellaneous Business Tasks Handle tasks as assigned that may span across any of the owner's businesses or personal needs. Coordinate between multiple locations including Moorestown office and farm residence. Exercise discretion and confidentiality at all times. Required Qualifications 3+ years of experience as an executive assistant, office manager, or similar role. Strong written and verbal communication skills – professional, clear, and confident. High proficiency in Microsoft Office Suite (Word, Excel, Outlook) and Google Workspace. Demonstrated ability to handle sensitive financial and legal information with strict confidentiality. Experience drafting contracts, leases, or legal correspondence a strong plus. Exceptional organizational and time‑management skills – ability to juggle multiple priorities. Self‑starter who can work independently with minimal supervision. Valid driver’s license and reliable transportation. Preferred Qualifications Experience supporting a multibusiness owner or high‑net‑worth individual. Background in real‑estate administration or property management. Familiarity with medical transportation, healthcare compliance, or regulated industries. Experience with QuickBooks or similar accounting software. Notary Public certification (or willingness to obtain). What We Offer A dynamic, ever‑boring role with real variety and responsibility every single day. Direct access and reporting to the owner – your work will have immediate impact. Competitive compensation based on experience. Flexible work environment across a professional office and unique farm/estate setting. Opportunity to grow alongside an expanding portfolio of businesses. A Note About This Role This position requires someone who is comfortable operating in a fast‑moving, entrepreneurial environment where no two days are the same. You will regularly shift between supporting a medical transportation company, a horse farm, real estate transactions, and a windows installation business. The right person will find this variety exciting — not overwhelming. Discretion, loyalty, and the ability to adapt quickly are not just desired — they are essential. #J-18808-Ljbffr Tri-state Medical Group