Special Assistant to the Founder - AI-Native (Remote, Part-Time to Full-Time)

Special Assistant to the Founder - AI-Native (Remote, Part-Time to Full-Time) Starts 4 hrs/day at $500-750/mo, scaling to full-time ($1,000-1,500/mo) as the role grows | Long-term | Direct to owner I run a maritime consulting and brokerage firm serving government contractors, built on an AI-first stack (Claude, automated market intelligence, custom scanners). I'm looking for a sharp, resourceful right hand - someone who works through AI daily and thrives on problems that don't come with instructions. What you'll own: The machine. Run research and daily tasks through Claude on your own seat, triage automated scanner output, and leave a morning handoff note: what ran, what's flagged, what needs my decision - with your recommendation. The follow-through. Every open thread - emails, pending documents, stale deals - has a next action and a date. Nothing slips. The improvements. Keep a friction log, send a short Friday memo (top 3 fixes, ranked by impact), and propose automation for anything done manually more than a few times - including my own work. Part of this job is watching how I operate, spotting what I do repeatedly, and turning it into systems: documented workflows, automations, and processes that run without either of us touching them. Push back when you think I'm wrong - I value judgment over agreement. Much of what lands on your desk will be half-formed: "figure out why this went quiet," "something's off in this data." If that sounds energizing rather than stressful, we'll get along well. You: experienced with AI tools beyond casual use (Claude a strong plus - show me something you've built or run with it), an exceptionally clear writer, organized, and comfortable working async with real autonomy. Camera-on standups at handoff. Process: short async Q&A → paid trial task ($50, ~3 hrs) → paid 30-day trial at 4 hrs/day → long-term. Hours and pay scale up (typically from 60-90 days) as the work you surface justifies it - your weekly improvement memos are the case for your own expansion. To apply, include the word "deadreckoning" in your first line, plus three sentences on the most interesting problem you've solved - with AI or without.