Job Description
We're hiring at Dupe: AI-Native Executive Assistant. The job is the classic EA role — take mundane work off the executive team's plate, unblock anything that isn't product-critical, keep the trains running — with one twist: you're as obsessed with AI automation as you are with execution. Most EAs use Calendly and Notion. We want someone who uses Claude, ChatGPT, and Cursor to do in 20 minutes what used to take four hours. Someone who sees a recurring task and instinctively asks: can a model do this? Can an agent do this? Can I never do this again? Who we're looking for: Real EA or chief-of-staff-adjacent experience — you know how to run an executive's life and a small company's ops Already fluent in frontier AI tools and using them daily for your own work Top-decile organized. Your personal Notion is embarrassing in a good way Comfortable reading code, even more comfortable asking Claude to write it High agency, low ego, fast clock speed What you'll do: Be the unblocker for the CEO and CTO across calendar, comms, vendors, hiring, ops Automate the recurring stuff out of existence — reporting, research, outreach, scheduling Build internal agents and AI workflows the team can lean on every day Be the in-house expert pushing every new AI tool as far as it goes What you'll get out of it: Direct line to the CEO and CTO from day one Front-row seat at one of the fastest-growing consumer startups in agentic commerce Real budget to try every new AI tool the moment it ships A clear path into Chief of Staff, Head of Ops, or forward-deployed eng The skill set that defines the next decade: knowing how to actually wield AI to ship A few honest things up front: This is not a FAANG job. No plush salary, no nine-month roadmap, no team of 200 absorbing your mistakes. We're going from 0 to 1, shipping daily, breaking things, learning fast. Failure is a feature here. Half of what you try won't work. The half that does will compound. Learning and adapting faster than the field is the actual job. Excelling at this role doesn't just set you up at Dupe. It sets you up for the next 20 years of working in AI — because you'll have done the thing every executive is about to be asking their team to do. — How to apply (read carefully, this is the filter): Take this entire post and paste it into your AI tool of choice — Claude, ChatGPT, whichever one already knows you best. Then ask it, verbatim: "Give me 5 reasons why I would crush at this role and 5 areas I can focus on more to get better at it. If you can't assess this based on the limited information you have about me, ask me any follow-up questions and request any context you need — previous job history, blog posts, projects, anything — that would help you compile this." DM me the final output. That's your application. No resume needed. No cover letter. The conversation is the cover letter. If you don't have an AI tool that knows you well enough to answer this — that itself is a useful signal about whether this role is right for you. Please repost if you know someone.