6-Week Live Cohort · 12 Seats · $3,000

The Operating System
Every Chief of Staff
Should Have Built
Six Months Ago.

Six weeks. Six systems built live, in your real tools, with a cohort of 12 operators and an expert expert AI developer in the room. You leave with an automation portfolio that reclaims 10+ hours every week — permanently.

10+
Hours reclaimed weekly — permanently
6
Live systems built across six weeks
12
Seats per cohort — intentionally small
100%
Company-reimbursable
Investment
$3,000
Per seat · Rolling applications · Cohorts fill fast
Space is limited — Secure Your Spot Now →
Who This Is For

Built for CoS operators who are done being buried in logistics.


You're in the role

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.

You're aiming for the role

Senior operators, EAs, and project leads positioning for their first CoS seat. Enter AI-fluent, not AI-curious — and signal that on day one.

The Curriculum

Six weeks. Six systems built.

Every session — recorded video + live workshop — ends with something real running in your stack. Not a plan. A system.

Week 1
AI Foundations for the Strategic Operator
Mindset + Tools

Stop thinking like a user. Start thinking like a systems architect. We rewire how CoS operators see AI — not as a chatbot, but as an always-on team of specialists. Your full stack gets set up in this session.

  • Build your personal AI stack — the 6 tools every CoS needs
  • Write prompts that produce principal-ready outputs on the first pass
  • Create your exec's voice document — the foundation of all AI-assisted comms
  • Audit your current role: identify your top 10 hours of automatable work
You Build This Week
Your AI Stack Setup + Executive Voice Document
Week 2
Automating the Communication Layer
Comms + Writing

The average CoS spends 40% of their time writing things their principal will rewrite. We fix that — and then eliminate the whole category of work. Five communication types, one system, zero revision cycles.

  • Build an AI-powered briefing system for exec prep
  • Create templates for board updates, stakeholder comms, and all-hands drafts
  • Set up automated meeting summaries with action item routing
  • Draft in your exec's voice without asking them a single question
You Build This Week
Automated Briefing System + Comms Template Library
Week 3
Workflow Automation Without Code
Operations + Zapier

Dan, our expert AI developer and co-facilitator, leads this session. You'll go from "I've heard of Zapier" to having real automations running by end of week. Every step done in your real tools, with your real workflows.

  • Map and automate your top recurring workflows
  • Build a weekly reporting pipeline from raw inputs to formatted output
  • Set up intake-to-action automation for requests, approvals, and escalations
  • Connect your tools: Slack, Notion/Airtable, Gmail, calendar — talking to each other
You Build This Week
1–2 Live Automations Running in Your Actual Stack
Week 4
Strategic Intelligence & Research Systems
Research + Analysis

A CoS who can synthesize faster than anyone else in the room is indispensable. We build the research and analysis workflows that make you that person — every time, for every high-stakes conversation.

  • Build a competitive and market intelligence pipeline
  • Use AI to synthesize multi-source documents into exec-ready narratives
  • Create a pre-meeting research system for any high-stakes conversation
  • Turn raw data into insight without a data analyst
You Build This Week
Research Intelligence System + Pre-Meeting Brief Template
Week 5
The AI-Augmented Operating Cadence
OKRs + Rhythm

Build the operating infrastructure that makes your entire organization run better — not just your inbox. This is where CoS work becomes institutional. Systems that surface the right information, automatically, to the right people.

  • Automate OKR tracking and progress narrative generation
  • Build an AI-assisted board pack assembly workflow
  • Create a decision log and institutional memory system
  • Design a weekly rhythm that surfaces the right information automatically
You Build This Week
Operating Cadence System + Board Pack Framework
Week 6
Leading Your Organization Forward & Future-Proofing Your Career
Career Strategy

The final session is about positioning — in your organization, in interviews, and in the market. We turn what you've built into a story that makes you irreplaceable. And we build the roadmap that keeps compounding after the program ends.

  • Articulate your AI fluency in interviews and performance reviews
  • Build a personal AI roadmap for continuous leverage
  • Present your automation portfolio to your cohort
  • Define the judgment work only you can do — and protect it
You Build This Week
Automation Portfolio + Personal AI Roadmap
What's Included

Everything you need. Nothing you don't.

Every element is here because it makes the thing it's attached to work better. No filler. No added-value fluff.

6 Live Implementation Workshops

60 minutes each, capped at 12 students. You watch the pre-recorded training video when your schedule permits during the week before the interactive session, then you come to the workshop and build in your actual tools, with your actual workflows. This isn't a tool demo. You are the demo.

AI Developer Co-Facilitator — Every Session

The thing no other CoS program has. A technical developer in the room for every workshop and every office hour. When your Zapier trigger isn't firing, you get a real answer in real time.

6 Weekly Office Hours

45 minutes each, the day after every workshop. Bring whatever broke overnight. Bring the edge case your specific stack created. Dan, our expert AI developer is in office hours too — this is where the real learning happens.

Tools & Templates Library

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.

Private Cohort + Alumni Community

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.

How It Compares

The format that makes the difference.

The systems are the same across formats. The question is whether you'll actually have them built by the end.


Feature Self-Paced Course 6-Week Cohort ✦ 2-Day Bootcamp
Pre-recorded video content
Live implementation sessions ✓ 6 sessions ✓ 4 sessions
expert AI developer in the room ✓ Every session ✓ Both days
Office hours Monthly drop-in ✓ Weekly (6 sessions)
Cohort community ✓ Private Slack
Systems built by program end Depends on you Built across 6 weeks 5+
Org-level AI roadmap
Price $597 $3,000 $925
Investment

The systems pay for themselves within weeks.



What You're Actually Getting
6 pre-recorded training training video modules (~60 min each)$1,200
6 live implementation workshops$6,000
6 weeks of weekly office hours$3,000
Expert AI developer co-facilitation (all sessions)$4,500
Tools & Templates Library$800
Private cohort + permanent alumni access$1,500
Total standalone value $17,000
Your investment $3,000

A CoS reclaiming 10 hours per week at a $120K salary recovers the full $3,000 investment within approximately 5–6 weeks — and the systems keep running indefinitely after that.

6-Week Live Cohort
$3,000
Per seat · Rolling applications · Company-reimbursable
6 pre-recorded training training video modules
6 live implementation workshops
expert AI developer in every session
6 weeks of office hours
Private cohort Slack
Tools & Templates Library
Permanent alumni community
Space is limited — Secure Your Spot Now →
12 seats per cohort. Not artificial scarcity — Dan, our expert AI developer can only give every stack the attention it needs at that size. When it fills, the waitlist opens for the next one.
Questions

Everything you're wondering about.


Do I need to be technical?

No. The expert AI developer and co-facilitator exists precisely for this. When your Zapier trigger isn't firing or your Claude prompt 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.

What if I miss a live session?

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.

What tools will I need?

Claude Pro ($20/mo), Zapier Starter (~$20/mo), Fathom (free), and Google Workspace. Notion is recommended but not required. We walk through setup in Week 1 and Dan, our expert AI developer helps anyone with a different stack adapt the builds to their tools.

Can my company pay for this?

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 5–6 weeks of reclaimed capacity. Most companies approve this without a second conversation.

How is this different from the 2-day bootcamp?

The bootcamp gives you the most critical systems in an intensive format. The cohort goes significantly deeper — more systems, more custom builds, weekly office hours, a cohort community that continues after the program, and a full org-level AI roadmap. If you want the full operating system, that's the cohort.

When does the next cohort start?

We run rolling applications with cohorts forming when 12 qualified applicants have been accepted. Apply now to be considered for the next cohort — we'll confirm your spot and send dates when the cohort forms. If it's full, you'll be placed on the waitlist for the following one.