Personal Assistant for Family Life, Vineyard & Airbnb Support

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We’re a family with a lot going on — a couple of businesses (including a vineyard and Airbnb), a consulting firm, kids, school schedules, and all the everyday life stuff that adds up fast. We’re looking for someone reliable, thoughtful, and organized to help manage the personal side of things so we can breathe a little easier. This role is mainly focused on helping us run life more smoothly, but may also include light support for our Airbnb, vineyard, or farm — things like ordering supplies, researching vendors, or making arrangements. We’d love to work with someone who’s proactive, great with follow-through, and genuinely enjoys helping things run behind the scenes. You don’t need to know everything — just be resourceful, responsive, and able to figure things out as you go. We prefer someone who is online/checks messages frequently. We’re also on Upwork daily and like to work with people who communicate clearly and consistently. Some Things You Might Do: Manage and update our family calendar (appointments, reminders, travel) Research and coordinate summer camps, kid activities, vacations, etc. Schedule doctor appointments, home repairs, car maintenance, etc. Help with small tasks for our Airbnb (ordering supplies, coordinating cleanings, etc.) Occasionally help with our vineyard or farm (vendor coordination, research, placing orders) Keep us organized by handling the small stuff so we can focus on the big stuff This Role Might Be Perfect for You If: You’re naturally organized and detail-oriented You like keeping things moving and hate letting tasks fall through the cracks You’re a clear, friendly communicator and ask questions when needed You’re tech-comfortable and good with online tools, calendars, and research You’re the kind of person people trust to “just handle it” You’re online and available regularly throughout the day Bonus If You Have Experience With: Supporting busy families or entrepreneurs Airbnb or hospitality platforms Researching and sourcing vendors or services Light admin or project coordination To Apply: Tell us a little about yourself and how you like to work. If you’ve helped a family or small business stay on top of life and logistics, we’d love to hear about it. We’re looking for someone who can stick around — someone who gets to know how we operate and becomes a natural extension of our team (and honestly, our family). This is a part-time, ongoing role with flexibility. We’re kind, respectful people and value communication, trust, and shared wins. Looking forward to meeting you!

Personal Administration Administrative Support Scheduling Virtual Assistance Communications