Claude AI Trainer & Onboarding Specialist for Small Team

Remote, USA
Posted Jun 14, 2026
Full-time

• *Claude AI Trainer & Onboarding Specialist for Small Team**
• *About the Role**

We recently set up a Claude Team account and need an experienced Claude AI specialist to onboard and train our team. This is a hands-on tutoring and setup engagement — not a generic AI training session. We need someone who truly knows Claude inside and out.
• *Schedule**

- Sessions will be held on **Saturdays only**

- Each session is **2 hours**

- All sessions conducted in **Eastern Time (ET)**

- We are looking to begin **this Saturday, April 18th**

- Additional Saturdays will be scheduled as needed
• *What You'll Be Doing**

- Conducting live, structured 2-hour training sessions with our team on Saturdays

- Walking team members through Claude's interface, capabilities, and best practices

- Configuring and explaining Claude's integrations and connectors, specifically:

- **Microsoft 365** (Outlook, Teams, SharePoint, etc.)

- **Claude in Chrome** (browser-based workflows and automation)

- **Cowork** (desktop task and file automation)

- Helping us identify and set up the most relevant **MCP connectors** for our workflows

- Reviewing and optimizing our **system prompts and user prompts** for maximum effectiveness

- Introducing the team to **Claude Skills** — including community-built skills available on GitHub — and helping us deploy the ones that fit our needs

- Providing guidance on team-wide best practices and prompt libraries
• *What We're Looking For**

- Deep, hands-on expertise with **Claude (Anthropic)** — not just general AI knowledge

- Demonstrated experience with **Claude's connector and integration ecosystem** (Microsoft 365, Chrome extension, Cowork, and similar tools)

- Familiarity with **Claude Skills and GitHub-hosted skill libraries**

- Strong understanding of **prompt engineering** specifically for Claude

- Experience training or onboarding non-technical users

- Clear, patient communication style — our team members are not all technical

- Ability to tailor sessions to different skill levels

- Must be **available Saturdays in Eastern Time**, starting April 18th
• *Nice to Have**

- Experience setting up Claude for business teams

- Familiarity with MCP (Model Context Protocol) server integrations

- Prior Upwork or freelance training engagements with verifiable reviews
• *To Apply, Please Include:**

1. **Your qualifications** — specifically what you know about Claude, its features, integrations, and ecosystem

2. **What you can do** — a clear summary of the skills and services you can deliver in these sessions

3. **Your training experience** — have you done this type of Claude or AI onboarding/training before? If yes, describe the engagement, who you trained, and what was covered

4. Any relevant testimonials, portfolio examples, or references from past training work

5. Your availability this **Saturday, April 18th (Eastern Time)** and preferred session time

6. Your hourly rate or proposed project rate

We are not looking for someone who has simply *used* Claude — we need someone who can confidently teach it, set it up, and guide a team through real-world workflows.

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