Build a Chief of Staff and a Content Manager AI Agent
In this live session, Jacqueline V. Twillie builds two AI agents with you in Gumloop, no code. A Chief of Staff AI agent turns your calendar and inbox into a daily brief and drafted replies. A Content Manager AI agent turns one piece of content into hooks, captions, a newsletter blurb, and a 7-day plan. Both draft. You decide and send.
This is for mid-career professionals and solo creators whose inbox and calendar set the pace of the day, and for anyone with a piece of content they made once and posted once. You don't need code or a technical background. Bring a laptop, a Google account you use every day or a short list of real open items to paste, and one thing you already made.
Where she taught it
- CultureCon 2026 BraindateOctober 3, 2026 · Brooklyn, New York
October 3 and 4. Both AI agents, with a build guide Jacqueline updates every week.
Follow-along page - CultureCon 2026 online encoreOctober 7, 2026 · Google Meet, 7 PM ET
Both AI agents built live inside the hour. 14 attended.
Follow-along page - Women Applying AIOctober 7, 2026 · Zoom, 12 PM ET
The Chief of Staff AI agent, in one hour. 26 attended.
Follow-along page
Chief of Staff AI agent
- Reads your calendar and inbox, or whatever you paste in
- Gives you today's calendar, the emails that need a reply, and your open loops
- Drafts each reply in your voice and tells you how urgent it is
- Looks up a person or brand before a call, from public information only
- Never sends, deletes, accepts an invite, or posts
Content Manager AI agent
- Reads one piece of content you already made, plus 2 or 3 samples of your own writing
- Gives you 3 to 5 hooks, captions per platform, a newsletter blurb, and a 7-day posting plan
- Writes the plan into a Google Sheet, or in the chat if Sheets is not connected
- Studies how you sound before it drafts anything
- Never posts, publishes, or schedules, and never invents a story, a client result, or a statistic
How to Reclaim Your Week When Your Inbox and Calendar Run You
If your inbox decides your morning, the fix is a short brief you ask for before you open it. A Chief of Staff AI agent builds that brief from your calendar, your email, and your open loops, and drafts the replies. It drafts. You send. These are the six moves, plus the Content Manager for the week ahead, with the lines from the instruction files and the build guide that Jacqueline teaches.
1.Give it three to five real items
Start with what is actually on your plate today: a reply you owe, a call, a decision, something you promised to send. Also write one sentence about the follow-up you keep meaning to do and don't. That sentence is the first real job your AI agent gets. If nothing is connected, this is the line your Chief of Staff AI agent opens with.
Paste in 3 to 5 things you need to track today, and I'll start from there.
2.Set the boundary first: it drafts, you send
Put the rule in writing in the instructions before you connect anything. Every reply is a draft, saved to Gmail drafts or written in the chat. A real calendar event happens only when you say 'add it' in that exact turn. Then check the connectors list yourself: no Slack, no CRM, nothing that posts. Gmail is the one that could send. The written rule comes first.
Every reply is a draft, and I send it myself.
3.Ask for the brief before you open your inbox
The brief comes in the same three parts, in the same order: today's calendar in time order, the emails that need a reply with a drafted reply and one line on urgency, and your open loops. Open it before the inbox. The sorting is already done.
Give me today's brief.
4.Make it name the open loops plainly
An open loop is a follow-up you owe, a decision you have not made, or a thing you said you would send and have not. The instruction file tells the AI agent to name each one and not to soften an overdue one into a suggestion. Overdue is the word you want to see.
Name each one plainly. Don't soften it into a suggestion if it's actually overdue.
5.Prep before the call
When a call is coming with a specific person or brand, ask for prep first. The research connectors are optional. The Chief of Staff AI agent uses the ones you have connected, Exa for recent news, Firecrawl for their website, Apify for public posts, and returns a one-page brief plus talking points or a drafted reply. If none are connected, it tells you plainly it is working from general knowledge only.
Prep me for my 2 PM.
6.Correct it once, in one sentence
Read what it gave you and tell it one thing that is off or missing: the tone of a draft, a task it skipped, a meeting it got wrong. With Self-Improving Instructions on, the fix carries into the next answer. The instruction file says to keep the fix and not quietly revert to the first version.
Keep the fix; don't quietly revert to the first version next time.
7.Turn one piece of content into your week
Once the inbox is handled, hand the Content Manager AI agent one thing you already made, a video, a caption, a newsletter, a pasted paragraph. First it asks for 2 or 3 samples of your own writing so it learns how you sound. Then it gives you hooks, captions per platform, a newsletter blurb, and a 7-day posting plan, each day with one line on why that day. It never posts. You do.
Turn this into a content pack.
Build both AI agents in one hour
The same five steps build both AI agents in Gumloop, no code, using the CultureCon 2026 instruction files. Build the Chief of Staff first, then the Content Manager. The second one goes faster. Jacqueline is a Gumloop ambassador and earns a referral if you stay on after the 14-day trial.
Step 1: Define a precise objective
Chief of Staff: turn your calendar and inbox, or a pasted list of open items, into a short daily brief plus drafted replies. Content Manager: turn one piece of content into a full content pack in your voice. Add your own sentence about the one thing you want off your plate. That is the first real job.
Step 2: Upload explicit instructions
Create each AI agent in Gumloop, name it, then use the plus button in the chat box to upload its file and send 'Use this file as your instructions.' The Chief of Staff file fixes the brief in three parts: today's calendar, emails that need a reply, open loops. The Content Manager file fixes the pack in four: hooks, captions per platform, a newsletter blurb, a 7-day plan.
Step 3: Turn on self-improvement
Turn on Self-Improving Instructions in each AI agent's settings. Then correct each one once, in one sentence. Both instruction files say to keep the fix and not quietly revert to the first version.
Step 4: Ground it in real data
Chief of Staff: connect Gmail and Google Calendar, or paste 3 to 5 real open items. Exa, Firecrawl, and Apify are optional research connectors that read public information before a call. They are not needed for the daily brief. Content Manager: paste 2 or 3 things you have written, then give it one real piece of content as a YouTube link to your own video, a Drive file, or pasted text. No Google login? A fictional sample inbox and sample content file are on the guide.
Step 5: Set strict boundaries
Check the connectors list yourself. It should hold only what you added for this build: Gmail, Google Calendar, and the optional research connectors for the Chief of Staff; Drive, YouTube, and Sheets for the Content Manager. No Slack, no CRM, nothing that publishes or posts. The written rule is what keeps Gmail to drafts. The Chief of Staff AI agent drafts replies, proposes holds, and never sends, deletes, or accepts an invite. The Content Manager AI agent writes drafts and never posts, publishes, or schedules. When you add a connector later from your own account, add the approval rule first.
What the AI agent never does
- The Chief of Staff AI agent never sends an email. Every reply is a draft, and you send it yourself.
- It never creates or moves a real calendar event on its own. It proposes a hold or a reschedule, and you confirm it, unless you say 'add it' in that exact turn.
- It never deletes anything in your inbox or your calendar.
- It never accepts, declines, or responds to a calendar invite for you.
- It never posts, publishes, or messages anyone outside the chat.
- Research connectors (Exa, Firecrawl, Apify) read public information only. None of them log into a private account or post anything.
- The Content Manager AI agent never posts, publishes, or schedules anything. Every output is a draft in a Sheet, a Drive file, or the chat.
- It never invents a personal story, a client result, or a statistic that is not in what you gave it or in your own voice samples.
Questions, answered
What is a Chief of Staff AI agent?
A Chief of Staff AI agent is a helper you set up once, in plain English, that turns your calendar and inbox into a daily plan. Jacqueline V. Twillie teaches it as a three-part brief: today's calendar in time order, the emails that need a reply with a drafted reply for each, and your open loops, the follow-ups nobody has closed. Before a call, it can also look up the person or brand from public sources. It drafts. You decide and send. Jacqueline builds it live in Gumloop with no code.
Can a Chief of Staff AI agent send emails for me?
Not the version Jacqueline V. Twillie teaches at CultureCon. Her instruction file tells the AI agent to save every reply as a draft and leave the sending to you. It also never creates or moves a real calendar event on its own, never deletes anything, never accepts or declines an invite, and never posts or messages anyone outside the chat. Her build includes a step where you check the connectors list yourself, so nothing that can send or post is attached. The AI agent drafts, and you send.
What does a Content Manager AI agent make from one piece of content?
Give it one piece of content you already made, such as a video transcript, a caption, a document, or a pasted paragraph, and it returns a content pack in your voice: 3 to 5 hooks that come at the piece from different angles, captions fitted to each platform you use, one newsletter blurb, and a 7-day posting plan, written into a Google Sheet when Sheets is connected. Jacqueline V. Twillie builds it to study 2 or 3 of your own writing samples first. It never posts or schedules anything.
Do I need to connect my inbox to build a Chief of Staff AI agent?
No. In Jacqueline V. Twillie's build you can connect Gmail and Google Calendar, or skip the connectors and paste three to five real open items into the chat. Either way the AI agent sorts them into the same three-part brief and drafts the same way. If you would rather not use anything real, she provides a fictional sample inbox and calendar built for the purpose. With nothing connected, the instruction file has the AI agent ask you directly for three to five things you need to track today.
Where did Jacqueline Twillie teach this build?
Jacqueline V. Twillie built both the Chief of Staff and the Content Manager AI agents at the CultureCon 2026 Braindate in Brooklyn on October 3 and 4, and again in an online encore on Google Meet on October 7, where 14 people attended. That same day she built the Chief of Staff AI agent with Women Applying AI on Zoom, where 26 attended. She has taught more than 400 people to build their first AI agent, and she updates the CultureCon build guide every week.