Proactive Executive Assistant for an AI-Forward Wine & Beverage Advisor (Long-Term)

I run a boutique advisory firm in the wine and beverage industry and also hold a senior role with a beverage company. That means a lot of moving pieces at once: multiple client engagements, internal projects, meetings, decks, financial models, and a constant flow of email and follow-ups. I'm looking for a sharp, reliable executive assistant to be my organizational right hand and help me stay on top of all of it. This is a long-term role. I'd rather invest in one great person and grow the relationship than cycle through task-takers. It starts at 10 to 15 hours a week, with room to increase as we build trust and rhythm. **A few honest things about how I work:** I have ADHD, so I move fast, jump between projects, and sometimes let threads slip. I'm not looking for someone to fix that. I want someone who builds the guardrails around it, holds the structure I don't naturally hold, and follows up when I go quiet. I also lean heavily on AI tools in my day to day (Claude, ChatGPT, Gamma, Fireflies, and others), and a lot of our work together will run through them. You don't need to be an expert, but you should be comfortable in that world, or genuinely eager to get there. **What you'd help me with:** - Keeping my calendar clean, current, and realistic. Scheduling, rescheduling, protecting focus time, catching conflicts before they happen. - Tracking projects and tasks across several concurrent workstreams so nothing slips, and maintaining one clear source of truth I can check any time. - Triaging and organizing my inbox. Surfacing what matters, filing what doesn't, drafting routine replies. - Turning meeting notes into action items and following them through to done. (I use Fireflies for transcripts.) - Organizing files in Google Drive so I can find things quickly. - Tracking client and partner follow-ups so I never drop a thread. - Light research and prep as needed. - Being the person who reminds me about the thing I said I'd do and didn't. **Who I'm looking for:** - Proactive by default. You follow up with me, not the other way around. You spot loose ends and close them without waiting to be told. - Comfortable with shifting priorities. My days change fast, and I need someone who rolls with that and helps me re-anchor instead of getting rattled. - A systems builder. You can set up simple, durable organization (calendar, task tracker, file structure) and keep it running with little input from me. - Comfortable with AI tools. You use them already or you're keen to learn. You can take a rough note or a messy draft and turn it into something clean. - Reliable and self-managing. If you say it's handled, it's handled. - Discreet. You'll see confidential client and financial information, and you treat it that way. - Strong written English. Clear, professional, low-drama communication. - Detail-oriented without being rigid. You sweat the small stuff without losing the bigger picture. **Tools:** - Google Workspace (Calendar, Gmail, Drive) is essential. - Comfort with AI assistants like Claude or ChatGPT is a real plus, since we'll use them daily. - A plus if you know a project management tool (Notion, Asana, ClickUp, or similar), Fireflies, or Gamma. - Not required, but welcome: any exposure to wine, beverage, hospitality, or consulting. **Logistics:** - 10 to 15 hours a week to start, long-term, with room to grow. - I'm based in California (Pacific Time) and I'm open to candidates anywhere. What matters to me is the schedule, not where you live. - The one fixed requirement is a couple of hours of live overlap each morning my time, Pacific. Depending on where you are, that might land in your morning, evening, or overnight. That's your call to make. If those hours work for your life, great. If not, no hard feelings. The rest of the week is async: I hand off tasks by email and shared files for you to pick up on your own schedule. Figure roughly half the week live with me, half independent. - Hourly, paid through Upwork. **To apply:** - Start your message with the word ORGANIZED so I know you actually read this. - Answer the screening questions properly, in your own words. No generic copy-paste. I read every word, and I'm looking for the person who understands what this role really is.