Freelance AI Trainer, Claude & Claude Cowork (1:1 Executive Training)

Overview

Trainee

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