AI on Autopilot: Making Claude Work While You Sleep | AICHR
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You've seen what Claude can do. You've built automations. Maybe you even set up that morning briefing from our last event. But here's the honest question: how many of those automations are you still running manually every time?
Most people try an AI workflow once, love it, and then forget to run it again by Wednesday. The problem isn't capability — it's consistency. You keep forgetting to ask.
This session fixes that. We're taking the automations you already know how to build and putting them on a schedule that runs without you. Daily. Weekly. Monthly. While you sleep, while you commute, while you argue with your alarm clock.
This is a live, demo-driven walkthrough. We're not talking theory. We're opening Claude Desktop, scheduling real tasks, and watching them work — all in Cowork mode, no coding required.
What we'll cover:
🔄 Two Levels of Automation
Level 1: Cowork Scheduled Tasks — runs on your desktop, no code, click-and-schedule simplicity. For everyone.
Level 2: Claude Code Routines — runs on Anthropic's cloud, laptop can be closed, API and GitHub triggers. For developers. (Launched April 14 — brand new.)
⚡ 10 Automations We'll Build Live:
- The Morning Briefing — calendar + email + priorities, ready before you wake up
- Inbox Zero at Dawn — email triage and draft replies waiting for your review
- The Self-Cleaning Downloads Folder — file organization at midnight, every night
- Meeting Prep That Beats You to Work — research brief 2 hours before your first meeting
- The Friday Report That Writes Itself — weekly summary compiled automatically
- Weekly Competitive Intelligence — competitor monitoring every Monday
- The Subscription Watchdog — monthly scan of recurring charges you forgot about
- Expense Reports on Autopilot — receipts processed every Friday
- Content Calendar Batch — week's social media drafts ready Monday morning
- The Weekend Cleanup Crew — digital housekeeping while you enjoy Saturday
🔗 Chaining: When Automations Talk to Each Other The real power: one automation triggers the next. Morning briefing flags an urgent email → draft reply auto-generates → you review on your phone over coffee → approved reply sends before you reach your desk. Three automations, zero manual triggers.
Who this is for: Anyone with a Claude Pro or Max subscription who's used Cowork at least once. If you attended our April 9 (Claude Code) or April 23 (AI Coworker) events, this is the natural next step. If you didn't, you're still welcome — the setup takes 60 seconds and we'll walk through it live.
Who this is NOT for: If you haven't installed Claude Desktop yet, start with our free setup guide (linked on the event page) before the event. We're spending our time scheduling and automating, not installing.
What you'll leave with: ✅ At least 2-3 scheduled automations running on your machine ✅ A free homework doc with all 10 prompts ready to copy ✅ The framework for building and chaining your own automations ✅ Access to the AI Automation Playbook ($29) for advanced patterns and developer-level Routines
Prerequisites: — Claude Desktop installed (claude.com/download) — Claude Pro ($20/month) or Max ($100+/month) subscription — Cowork mode accessible (click "Cowork" at the top of the app) — Gmail and Google Calendar connectors set up (for the email-based demos)
🎙️ Your Speaker Andrew Stafford Co-Lead of The AI Collective Hampton Roads. 25+ years across technology, cloud architecture, and AI — including work with Amazon, NASA, healthcare platforms, and enterprise systems. Author of AI for Business. Currently building at the intersection of AI tooling, agentic workflows, and practical business automation.
🏢 For Businesses Want to bring AI automation training to your team? We offer private workshops (lunch and learn, half-day, full-day bootcamp), conference speaking, and technical consulting. Book a discovery call
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🤝 Organizers & partners
Organizers
The AI Collective Hampton Roads
Platinum partners
TechArk
Regent University
ECPI University
Hampton Roads Chamber Foundation
Retail Alliance & Retail Alliance Foundation
Bronze partners
Assembly
757 Collab
🌍 Our parent org
The AI Collective is a global non-profit community uniting 225,000+ pioneers – founders, researchers, operators, and investors – exploring the frontier of AI in major tech hubs worldwide. Through events, workshops, and community-led research, we empower the AI ecosystem to collaboratively steer AI’s future toward trust, openness, and human flourishing.
All attendees and organizers at events affiliated with The AI Collective agree to our privacy policy and are subject to our code of conduct. Additionally, by registering for this event, you agree to The AI Collective Hampton Roads chapter photo & video policy.