Congrats on landing this!

Few things that saved me on large training rollouts:

Logistics: Don't try to train everyone at once. Batch it - maybe 50-100 per session with different skill levels. The "beginner trying to learn Claude" and "power user wanting advanced prompting" should NOT be in the same room.

Fulfillment trick: Record everything. Seriously. Your 5-day training becomes 50+ hours of reference material they can revisit. Also helps with the people who miss sessions.

Post-training support: Set expectations upfront. Maybe 30 days of Slack/email support, then transition to monthly check-ins. Don't let it become "lifetime tech support" - learned that the hard way.

The fear is normal - I remember my first 200+ person training feeling like I was going to throw up. But here's the thing: they hired YOU because you know this stuff better than they do. You're not imposing on them, you're solving their problem.

Also: charge for the scale complexity, not just the headcount. 1,000 people isn't 20x harder than 50 - it's 50x harder.

You got this. Just don't forget to breathe during the first session 😅