Freelance AI Trainer, Claude & Claude Cowork (1:1 Executive Training)
Engagement type: Short-term freelance/consulting
Location: Doha, Qatar - in-person
Trainee: senior executives
About the engagement
We're looking for an experienced AI productivity coach to deliver a structured, hands-on training program for our senior executives on Anthropic's Claude, with a specific focus on Claude Cowork, Anthropic's agentic desktop product for knowledge work. The goal is to make our senior executives genuinely productive with Claude in their daily workflow within 2–3 weeks: drafting, document review, research synthesis, benchmarking, file organization, report generation, and delegating multi-step tasks to Cowork.
This is not a generic intro to AI workshop. We need a practitioner who already uses Claude and Cowork daily and can teach an executive how to think in terms of outcomes, projects, skills, and connectors, not just prompts.
What you'll deliver
A 4–6 session training program (1–1.5 hours per session, spaced over 2–3 weeks) covering:
- Session 1 — Claude fundamentals for executives. Chat vs Projects vs Cowork, picking the right model, working with Artifacts, file uploads, voice input, mobile + desktop pairing, settings and privacy basics.
- Session 2 — Claude Cowork core. Setting up the desktop app, the Cowork task loop (plan → execute → steer), Ask-before-acting vs Act-without-asking modes, reviewing Claude's plan, course-correcting mid-task, and end-to-end practice on a real document workflow.
- Session 3 — Projects, skills, and connectors. Organizing recurring work into Cowork Projects with persistent instructions and memory, using built-in skills (docx, pptx, xlsx, pdf), and connecting Google Drive, Gmail, Calendar, and other relevant services.
- Session 4 — Real executive workflows. Live build of 5 projects workflows tailored to senior executive actual job: board pack synthesis, contract review, investor update drafting, inbox triage, file/folder cleanup, and report generation from scattered sources.
- Session 5 — Steering long-running tasks & safety. When to supervise vs walk away, permission management, working with sensitive documents, what not to put into Claude, and recognizing when Claude is off-track.
- Session 6 — Advanced & wrap-up. Claude in Chrome, Computer Use, custom Projects setup, prompt patterns for executives, and a personalized playbook document the SE can refer back to.
- Plus: A written 1-pager cheat sheet and personalized playbook delivered at the end of the engagement.
Required experience
- Demonstrable hands-on experience with Claude Cowork (not just Claude chat or ChatGPT). Please share specific examples of workflows you've built or tasks you've automated.
- Strong working knowledge of Claude Projects, Skills, MCP connectors, and the Claude desktop app
- Prior experience training non-technical senior executives
- Comfortable working with confidential business documents and discussing real workflows under NDA.
- Excellent English communication. Arabic is a plus.
Nice to have
- Background using Claude Code or experience as a Claude power user / consultant.
- Familiarity with the GCC business context.
- Experience producing training collateral (cheat sheets, video walkthroughs, playbooks).
How to apply
Please submit:
- A short proposal (max 1 page) describing your approach to this engagement.
- Evidence of your Claude/Cowork experience (submit loom vidos), you will be asked to demonstrate Claude projects in the evaluation
- Earliest available start date.
