A-Player Executive Assistant

The Role - A-Player Assistant & Jack of All Trades We're a busy founder-couple doing consulting work while launching a new business. We have zero bandwidth for admin, personal life management, or hand-holding an assistant. We need an exceptional, proactive A-player who becomes the central hub for our business and personal lives, gets things done, is our right-hand person, proactive, independent, reliable, hard-working, honest, and builds their own structure without needing it handed to them. Core Responsibilities: Project & Freelancer Management - Run and keep organized our ClickUp board - both business and YouTube content boards. Manage contractors/freelancers end-to-end: bookkeeper, video editor, thumbnail designer, errand runner, cleaner, and others - you drive every workstream to done. - Get creative in how you source, interview & manage contractors - you don't wait to be told how, you figure it out. YouTube & Content (B2B AI channel) - Own the channel: video ideas, scripts, thumbnail/headline research, and overall YouTube strategy. - Manage our video editor and thumbnail designer; review and give feedback on videos and thumbnails before they go out. - Ideally, build a repeatable content system in Claude (idea generation, research, scripting) - not just use AI, but design a system with it. - Because this is an AI/B2B channel, you should genuinely be into AI - staying current on trends and topics, not just familiar with the tools. Recruiting & Sourcing Freelancers - Post roles across Upwork, Fiverr, LinkedIn, Indeed, and other job boards as needed for freelancers. - Proactively source, screen, and interview candidates. - Deliver a ranked shortlist with clear recommendations and test each freelancer via paid trials to find the best one. Admin & Research - Heavier on research and phone calls - chasing down information from vendors, banks, refund providers, software companies, etc. - Data entry, file organization, and similar admin work as needed. Light inbox/calendar management. Lead Gen & Outreach - Run high-volume outreach (email/LinkedIn, podcast pitching, partnerships) with a sales and numbers-game mindset. - Comfortable with basic data scraping/outreach tools (e.g., Apify, Apollo) to work efficiently. Personal Life Support - Travel planning, appointment scheduling, gift research, subscription management, Amazon returns. Ongoing personal projects - examples of real tasks you'd handle: Required Background: - 5+ years supporting founders, entrepreneurs, or business owners - no exceptions. - Excellent written & spoken English. - Years of experience working EST time zone, available 12:00 PM – 8:00 PM EST Time Zone. - Able to start at 20 hrs/week, with potential to grow if a right fit. - Not spread thin across many other clients - we need a lot of your capacity and dedication. - Experience with EA, project management, personal assistance, lead generation, Youtube, and AI. - Willing to do volume and thinks everything in terms of a “numbers game”. - Independent, proactive, reliable, gets sh*t done mentality. No excuses, rolls up your sleeves & figure it out type. - Proven A-player delivering high quality work held to a very high standard. - Hungry, entrepreneurial, and willing to work on the weekends. - 100% HONEST. Who You Are: - A bulldozer - assertive, hungry, a go-getter who pushes back and speaks up when needed. - Proactive and independent - you figure it out and bring solutions, not just problems. - Comfortable wearing many hats; a fast learner with a genuine growth mindset. - Willing to grind - late hours or weekends when needed. We reward that. - Extremely organized and detail-obsessed - your work is close to flawless; we rarely need to correct it. - Honest, high-integrity, and completely straight with us - no shortcuts, no covering mistakes, no surprises later, no lying. - Capable of 4–8 hours of focused, deep work at a time without distractions. - Uses your brain and human judgment, not just handing AI work on autopilot - knows when a task needs your brain vs. Claude, you never hands us copy-pasted AI slop as finished work, or without you properly vetting it, and you don’t outsourcing everything to AI and dull your brain/skills. You need to know the fine-line between when to use Claude vs when to do something manually the old fashioned way. Tools You Should Know: - Claude - the #1 requirement. Real, deep fluency: able to use it well without producing "AI slop." - You know Skills, Projects, Cowork, Dispatch. Bonus if you know Claude Code and Design. You should be genuinely into AI and actively leveling up your own Claude and AI skills - this matters extra given our Youtube channel is AI-focused. - Canva, ClickUp, Gmail/Outlook, YouTube, LinkedIn, standard job boards, Apify, Apollo, OneDrive, VidIQ, ChatGPT, Upwork. - Bonus: AI/automation tools like n8n, make.com and tech-savvy.