Six weeks. Multiple systems built live, in your real tools, with a cohort of 12 operators and an expert AI developer in the room. You leave with an automation portfolio that reclaims 10+ hours every week — permanently.
Current Chiefs of Staff at Series A–C companies who want to operate at a fundamentally higher level. You know your work. You're missing the system.
Senior operators, EAs, and project leads positioning for their first CoS seat. Enter AI-fluent, not AI-curious — and signal that on day one.
Every session — recorded video + live workshop — ends with something real running in your stack. Not a plan. A system.
Complete your self-paced training video on your own schedule during the week, then join the live implementation session every Tuesday at 11am ET / 8am PT / 4pm BST to build in your actual tools with expert guidance. Next cohort starts the week of May 4.
Stop thinking like a user. Start thinking like a systems architect. We rewire how CoS operators see Claude Cowork — not as a chatbot, but as a platform that can act, not just respond. You'll set up fully and run your first real workflows before the session ends.
Without context infrastructure, you re-explain yourself every session. This week builds the three-layer system — Global Instructions, Project Instructions, and CLAUDE.md — so Cowork already knows you, your CEO, and your org before you type a word.
Matt, our AI and technology strategist and co-facilitator, leads this session. This is where Cowork stops working with files and starts working with your entire world. Connect your tools and run the cross-system workflows that used to require four open tabs and an hour of copy-paste.
CoSs support 15–25 meetings a week. This module builds the full meeting lifecycle — prep, processing, follow-up — and covers every executive communications type, sourced from real data and drafted in your CEO's voice. Plus the hiring and onboarding workflows that define a high-leverage CoS.
Everything you've built so far, converted into one-click Skills and scheduled to run without you. You wake up. Your morning briefing is in your inbox. Your CEO's context packet is ready. The meetings on your calendar already have prep briefs. You didn't do any of it.
You've built the system. Now you lead the org through it. The CoS has the cross-functional visibility, executive trust, and — after this program — the technical fluency to drive company-wide AI adoption. This capstone session shows you how.
Every element is here because it makes the thing it's attached to work better. No filler. No added-value fluff.
Capped at 12 students. Every Tuesday at 11am ET / 8am PT / 4pm BST, starting the week of May 4. You watch the pre-recorded training video at your own pace during the week, then come to the live session and build in your actual tools, with your actual workflows. This isn't a tool demo. You are the demo.
The thing no other CoS program has. A technical developer in the room for every workshop and every office hour. When something isn't working in your Cowork setup, you get a real answer in real time — not a forum post.
Your learning doesn't stop when the cohort ends. The private community includes bi-weekly trainings with guest experts, live workshops, and ongoing updates as AI continues to evolve — so your skills compound long after the program wraps.
Battle-tested prompts and workflow blueprints organized by CoS use case. Communications, research, synthesis, operations, board prep. Built specifically for this role, tested in real CoS stacks.
Your cohort of 12 operators, plus every alumni cohort before you. The network that compounds — when one person finds something useful, they share it. Access never expires.
This isn't a productivity gain. It's capacity recovery.
A Chief of Staff earning $150K represents roughly $72 per hour of leadership capacity.
Reclaiming 10 hours per week through AI-powered systems returns ~$720 of capacity every week.
At that rate, the $3,000 investment is recovered in about four weeks — and the systems continue paying dividends indefinitely.
No. The expert AI developer and co-facilitator exists precisely for this. When your Cowork setup isn't behaving as expected or your workflow is producing inconsistent output, you have a technical expert in the room — not a forum post. The hard part of automation is seeing your workflows clearly, which is exactly what CoS operators are trained to do.
All sessions are recorded and available in the course portal. Office hours recordings are also saved. That said — the live sessions are where you get your specific stack built and unblocked. We strongly recommend attending live when possible.
Claude Pro or Claude Max ($20–$100/mo depending on tier) and Google Workspace — that's it. Everything is built inside Claude Cowork. We walk through setup in Week 1 / Module 1 and Matt, our AI and technology strategist, is there to troubleshoot any setup issues live.
Yes — most companies reimburse this as professional development. A CoS reclaiming 10 hours per week at a $120K salary recovers the $3,000 within approximately 4–5 weeks of reclaimed capacity. Most companies approve this without a second conversation.
The next cohort starts the week of May 4. Live implementation sessions run every Tuesday at 11am ET / 8am PT / 4pm BST for six weeks. You'll complete your self-paced training video at your own pace during the week, then join the live Tuesday session to build. Seats are limited to 12 — apply now to secure your spot. If the cohort is full, you'll be placed on the waitlist for the next one.