Personal Assistant – Woodstock, NY

Job Description I am seeking a reliable, organized, trustworthy, and flexible Personal Assistant to assist me with a variety of personal, household, organizational, and administrative responsibilities. This is primarily an in\-person position at my home in Woodstock, New York, so applicants must live within a reasonable commuting distance and be able to come to my home on a regular basis. The exact responsibilities of the position will evolve based on my needs and the strengths of the person hired. I am looking for someone who enjoys variety and is comfortable handling everything from errands and household organization to scheduling, research, phone calls, appointments, and administrative projects. The ideal person will be dependable, resourceful, detail\-oriented, comfortable working independently, and willing to take initiative. Most importantly, I am looking for someone I can trust and develop a comfortable long\-term working relationship with. Schedule This is a part\-time position with flexible and variable hours. Hours will generally fall between approximately 12:00 PM and 5:00 PM, although the number of hours needed will vary from day to day. For example, during the first several weeks, I may need approximately 4–6 hours of assistance on certain days as we get organized and establish routines. On other days, I may only need assistance for 1–2 hours. The schedule will therefore not necessarily consist of the same number of hours every day. Flexibility is important. Because many responsibilities will involve my home, errands, appointments, and other local activities, this is not a remote position. Applicants must be able to come to my home in Woodstock, NY on a daily basis when needed. Possible Responsibilities Responsibilities may include some or all of the following. The final responsibilities will be determined based on my needs and the abilities and interests of the person hired. Personal Assistance \& Errands Manage and coordinate my calendar, schedule meetings, appointments, and business travel arrangements with precision and efficiency. Provide comprehensive administrative support, including drafting correspondence, preparing reports, and transcribing meetings using transcription tools. Organize and facilitate events, meetings, and internal functions to ensure seamless execution from planning to follow\-up. Handle internal communication channels effectively, ensuring timely dissemination of information across teams and departments. Maintain accurate records through data entry, filing systems, bookkeeping using QuickBooks, and managing confidential documents with discretion. Assist with project coordination by tracking deadlines, preparing agendas, and collaborating with various teams to meet objectives. Utilize productivity software such as Microsoft Office Suite (Word, Excel, PowerPoint), Google Workspace, and video conferencing software for virtual meetings. Driving me to appointments Picking up prescriptions, dry cleaning, packages, takeout, and other items Making returns and exchanges Personal shopping Researching products and services before purchases Ordering items online Purchasing and organizing gifts Taking packages to UPS, FedEx, USPS, etc. Handling other miscellaneous personal errands as needed Skills Proven experience as a Personal Assistant or Executive Assistant. Strong organizational skills with the ability to prioritize tasks efficiently in a fast\-paced environment. Excellent written and verbal communication skills coupled with professional phone etiquette. Technical proficiency in Microsoft Office (Word, Excel, Outlook), Google Workspace (Gmail, Calendar), QuickBooks, DocuSign, and video conferencing platforms like Zoom or Teams. Demonstrated ability to handle confidential information responsibly while maintaining discretion at all times. Experience in event planning and organizing corporate or personal events from inception to completion. Adept at managing multiple projects simultaneously with high attention to detail and accuracy in data entry and transcription tasks. Household Assistance \& Organization Helping keep household projects and responsibilities organized Scheduling household repairs and maintenance Contacting and coordinating plumbers, electricians, landscapers, cleaners, contractors, and other service providers Keeping track of household maintenance needs Organizing closets, cabinets, storage areas, paperwork, and household items Helping maintain general organization throughout the home This is not primarily a housekeeping position, although occasional light household tasks and organization may be part of the job. Administrative Assistance Making telephone calls on my behalf Writing or responding to routine emails Organizing mail and identifying items requiring attention Sorting and organizing paperwork Filing and maintaining records Scanning, printing, copying, and organizing documents Completing online forms Keeping lists, spreadsheets, and records Researching information online Contacting businesses and service providers Following up on outstanding issues Assisting with miscellaneous personal administrative projects Research \& Problem Solving I would particularly value someone who is comfortable being given a problem or objective and figuring out how to handle it. Examples might include: Researching local service providers Finding a contractor or repair person Researching products before purchasing Finding restaurants, activities, or services Obtaining quotes and estimates Researching travel options Finding solutions to household or personal administrative issues Making calls and following up until an issue is resolved Travel \& Planning Depending on my needs, responsibilities could also include: Researching flights and hotels Making travel reservations Organizing travel itineraries Arranging transportation Making restaurant and activity reservations Keeping travel confirmations organized Helping prepare for upcoming trips Handling miscellaneous travel\-related arrangements General Personal Support Because this is a personal assistant position, there will occasionally be tasks that don't fit neatly into a specific category. I am looking for someone who is comfortable with a position where responsibilities can change from day to day. One day may involve making phone calls and organizing appointments, while another may involve running errands, researching a purchase, meeting a repair person, organizing paperwork, or helping solve an unexpected problem. Ideal Candidate The ideal candidate will be: Extremely reliable and punctual Trustworthy and discreet Highly organized Detail\-oriented Friendly and easy to communicate with Comfortable working independently Resourceful and good at solving problems Able to prioritize multiple tasks Comfortable with changing priorities Flexible regarding the number of hours needed from day to day Comfortable making telephone calls and dealing with businesses and service providers Comfortable using email, the internet, online shopping, calendars, and basic computer applications Able to follow instructions carefully Willing to ask questions when something is unclear Able to take initiative rather than requiring constant supervision Comfortable working in a private\-home environment Respectful of privacy and able to maintain confidentiality Previous experience as a personal assistant, household assistant, executive assistant, administrative assistant, office manager, household manager, concierge, or similar position would be helpful, but I am also open to someone without formal personal\-assistant experience who has the right combination of reliability, organization, judgment, and common sense. Transportation Because this position requires working at my home and may involve local errands: You must have reliable transportation You must be able to commute to Woodstock, NY A valid driver's license and good driving record are preferred You should be comfortable driving locally for errands when necessary Hours Part\-time / variable schedule Typical working window: approximately 12:00 PM–5:00 PM The actual number of hours will vary. Some days may require several hours of assistance, while other days may require only 1–2 hours. Applicants should therefore be looking for a position where flexibility is more important than having an identical schedule every day. Compensation Compensation will be dependent on your experience and expertise. I will add mileage reimbursement, paid time off, guaranteed minimum hours, and other benefits. About the Position I am hoping to find someone interested in developing a long\-term working relationship, rather than someone simply looking for a temporary position. The right person will gradually become familiar with my preferences, routines, household, and the way I like things handled. As trust develops, I expect that person will be able to take greater ownership of responsibilities and anticipate things that need to be done without waiting for detailed instructions each time. Confidentiality and discretion are extremely important because the person hired will be working in my home and may have access to personal information. How to Apply Please submit your resume along with a brief message answering the following: Where do you currently live, and approximately how long would your commute to Woodstock, NY be? What experience do you have that you believe would make you a good personal assistant? Are you generally available between approximately 12:00 PM and 5:00 PM on weekdays? Are you comfortable with a schedule where the number of hours may vary from day to day? Do you have reliable transportation? What hourly compensation are you seeking? Please tell me a little about yourself and why this particular position interests you. Please note: This is an in\-person position in Woodstock, NY and is not a remote personal assistant position. Pay: $25\.00 \- $35\.00 per hour Expected hours: 20\.0 – 30\.0 per week Benefits: Flexible schedule * Paid time off Work Location: In person