Chief of Staff / Executive Assistant to Founder with AI Tool Expertise
Chief of Staff / Executive Assistant to Founder with AI Tool Expertise Location: Remote | Hours: 8:00 AM - 11:00 AM ET | Compensation: $2,000/month base + large performance bonuses The Opportunity This isn't just an assistant job. It's a front-row apprenticeship with a founder operating across three worlds at once: an options hedge fund backed by Rockefeller family capital and senior execs at Morgan Stanley and Google, a growing personal brand and content engine, and whatever comes next. You'd be the right hand. The person I trust with every part of the business. You learn how a fund gets built, how capital gets raised, how audiences get grown, and how founders actually spend their time - by doing it alongside the Founder at every step. What You'll Actually Do This role is wide on purpose. Expect to touch all of it: Fundraising & investor relations: LP pipeline, DDQ prep, outreach, CRM, deck maintenance Content & social media: help grow the founder's audience across X, LinkedIn, TikTok, Instagram - script ideas, edit short-form video, post, track analytics, test hooks AI: build automated tools and news scanners to gather important information for making trades. Hands-on experience with actual data used to make real trades Get shit done: Figure out how to get things done. You can think creatively and solve problems. Travel: trips with the founder (fully covered) for investor meetings, conferences, content shoots, fundraisers The job will change as the businesses change. Flexibility is the role. Who You Are Fluent with AI tools (Claude, ChatGPT, Notion AI, Descript, CapCut). If you can't 10x yourself with AI, skip this one. Obsessive about details. Things get done correctly and on time, every time. Think three moves ahead. Surface what the founder forgot. Propose solutions, don't just flag problems. High trust and discretion. You'll see sensitive financial, investor, and personal information daily. Loyal to death and eager to learn. I will personally teach you everything I know. But if I spend that much time teaching you, I'm looking for someone who will ride or die with me. Comfortable on camera and with public-facing content
Nice to Have
Video editing, design, or a social media account you've grown yourself (your own numbers count) Finance coursework, trading club, or personal investing Shipped side projects - software, audiences, businesses, anything you built in college What You Get $2,000/month base Large performance bonuses tied to fundraising, growth, and operational milestones All travel, lodging, and meals covered when traveling with the founder Direct, daily mentorship on capital raising, trading, content, and founder-mode operations Proximity to a backer list most finance grads never see until they're a VP Path to expanded scope and comp as the businesses scale - the ceiling here is whatever you build it to be