AI Second Brain Engineer — Obsidian Vault Builder Who Connects Knowledge to AI (Experimental)

This is not an AI-slop job ad. Read or waste your credits. I'm Tyler, Chief of Staff at InsideSuccess.TV. We're building the Netflix of Business TV. I'm looking for someone who is obsessed with Obsidian. Not interested in Obsidian. Not "familiar with" Obsidian. Obsessed. I want someone who has already spent serious time building their own second brain. Someone who has a vault with hundreds of notes and real connections between them. Someone who has tried Dataview and Templater and QuickAdd and probably five other plugins I haven't heard of. Someone who has opinions about MOCs versus folders versus tags and can argue their position for 20 minutes. Someone who has connected their vault to AI — whether that's Claude, GPT, a RAG pipeline, a local model, or something they hacked together — and can show me how it works. This is a genuinely new space. Almost nobody has deep experience building organizational knowledge graphs connected to AI. I know that. But the people who are passionate about it have already been building one for themselves. They didn't wait for a job posting. They started because they couldn't help it. That's who I'm looking for. I don't care about where you went to school or your Upwork profile that claims you are great at everything. I care about your vault. Show me the graph. Show me the connections. Show me what you've built. This is an intense, high-expectation work environment. It is NOT for most. We have high turnover. You will be thrown into a fire and expected to solve problems. About the Role We are building a company-wide knowledge layer. Think your personal Obsidian vault but at the organizational level. Every concept, decision, transcript, process, and piece of context connected to everything else. Sales transcripts linked to marketing strategy linked to customer patterns linked to hiring philosophy. One connected substrate where the AI tools we build are nodes that read from and write into that substrate. Most companies have AI as six disconnected documents in six disconnected tools. Ours connects. That's the moat. Once the substrate is built, every new tool we add gets smarter because it sees the rest of the system. Competitors can buy the same models. They can't buy this. Your job is to architect that layer. You already think this way for your own brain. We need you to think this way for an organization. You will design the knowledge architecture, define how information gets structured and linked, build the connections between our knowledge base and our AI tools, and make sure the system compounds over time instead of just getting bigger. The first chunk of work includes designing the knowledge architecture for the AI department, building connections between our tools including Monday.com, Slack, GitHub, and Claude, creating the documentation and context-capture standards, and building AI agents that can actually query and reason across the connected knowledge. Requirements — Has a real Obsidian vault they have built over months not days — Understands wikilinks, backlinks, metadata, YAML frontmatter, and graph-based thinking — Has used plugins like Dataview, Templater, QuickAdd, or similar — Has connected Obsidian or any knowledge system to AI in some way — Systems thinker — OpenClaw or Hermes familiarity is a plus — Prompt engineer who understands context engineering — Comfortable with APIs and automation — Documents as they build Job Details — Rate: $7/hr — This is a work trial. My goal is to get you a raise. I want you to make as much money as possible. But it needs to be justified by value added. — Hours: Mon–Fri, 9:00 AM – 5:00 PM EST. Those are the required hours. Work more if you want, as the rest of us do. How to Apply Just answer the questions below. I'm not reading anything AI-generated. 1. What is your dream job? Be specific. No wrong answers. Do not say what you think I want to hear. One sentence. 2. What is one thing you enjoyed learning about this week? Does not need to be work related. One sentence. 3. Why are you better or different than other applicants? One to two sentences. 4. Share one favorite quote. No AI. Make one up and quote yourself. 5. What is the thing you have built that you are most proud of? One to two sentences. Include a link. 6. Who are you? Why would you apply to a job like this? Do not say family or money. What makes you tick? One to two sentences. 7. Tell me one thing you discovered about AI that was surprising, annoying, humorous, or insightful. One to three sentences. 8. How many hours have you spent building your second brain or knowledge system in Obsidian? Describe your vault. How many notes, what structure, what plugins, and what makes it yours. If you do not have a vault, be honest. 9. Have you connected your Obsidian vault or any knowledge system to AI? Describe exactly what you built, how it works, and what it does. If you have not done this yet, describe specifically how you would approach it. 10. Anything else you want to share? Optional. Thanks, Tyler