The unusually helpful AI assistant for Chiefs of Staff

for Chiefs of Staff

Townies like Sunny proactively sort the office’s mail, prep every leadership meeting, and chase the follow-through.

Meet your Townie

Your Townie holds that picture, tells you what’s slipping before your principal asks, and does the chasing and the drafting the way you would. Anything that leaves the building waits for your approval.

AI that learns you.

Your Town Wiki is a single place to see everything your Townie has come to understand about you. It’s a living synthesis of your profile, your work habits, and your preferences.

Isla Ferreira

Recent updates

• Moved the November board run-up into Goals after Lena Ostrowski confirmed the date and the pre-wire calls went on the calendar.
• Noticed she drafts the leadership agenda on Sunday evenings and logs decisions the same day they happen, and wrote both into How she works.
• Retired the note on the vendor renewal that closed, and flagged that Lena Ostrowski is still waiting on the metrics Matteo Ricciardi promised her.

Overview

Isla Ferreira is chief of staff to Matteo Ricciardi, the CEO of Cobalt Ridge, a sixty-person software company. She runs the office of the CEO: the operating cadence, the board run-up, the goals, and the special projects laid out in Projects.

How she works

Isla drafts the leadership agenda on Sunday evening and walks it with Matteo Ricciardi before Monday's sync. Decisions get logged with an owner the same day, because a decision nobody wrote down gets made twice.

The board run-up starts four weeks out: materials first, then a pre-wire call with each director, so nothing lands cold in the room. Femi Adeyemi holds the calendar while Isla holds the thread.

She ghostwrites much of what leaves the office, and every draft waits for a review before it sends, hers or Matteo's. The work in Projects is built around that discipline.

Goals

• Land the November board meeting with the pre-reads out a week early and every director pre-wired before the room, working back from the date with Lena Ostrowski.
• Get decisions and commitments out of scattered threads and into one record, so nothing leadership settled gets relitigated a quarter later.
• Make the invisible work visible: a running log she can point to when someone asks what the office of the CEO actually does.

Projects

The November board run-up is four weeks out. The agenda is drafted, the pre-reads are being collected from each lead, and the pre-wire calls with Lena Ostrowski and the other directors are on the calendar.

The pricing decision is with Jae Won Seo: the model gets updated this week, and the board sees the recommendation before anyone announces it.

The rest of the cadence runs here too: the weekly leadership sync, the quarterly goals review, and the offsite that still needs a date.

Your Townie stays on top of your inbox.

Understand what’s important

Inbox 6 new

• Leadership
  • Jae Won Seo: Pricing decision memo
  • Matteo Ricciardi: Can you run the offsite?
• Board & investors
  • Lena Ostrowski: Thoughts on the agenda
• Team asks
  • Femi Adeyemi: Thursday travel holds

The office of the CEO, sorted before you open it. A board member rises to the top, leadership threads land together, investor mail gets its own lane, and the newsletters wait somewhere you can still find them.

Explore the routine

Don’t drop the ball

Open commitments: 3 still open · oldest 11 days

• Send Lena the metrics Matteo promised
• Send Femi the travel approvals
• Collect Jae's board pre-read
• Send the QBR pre-read out
• Review the investor update draft

Your Townie does the planning so you don’t have to.

Leadership sync slot Week of 3 Nov PT

3 calendars Before Thu 60 min

One slot that clears three executive calendars. Availability, time zones, and the prep time you guard before a board week get reconciled in one pass, so finding an hour stops costing you one.

Your Townie helps you manage your meetings.

Show up prepared

Monday leadership sync Tomorrow 9:00 AM · 6 attendees Brief

• Last agenda
• Meeting notes
• Mail threads
• Goals doc

What needs an owner

• The launch retro has no owner yet.

Assembling

Sunny is assembling the meeting brief

Walk into the leadership meeting ahead of it. The open decisions, what changed since last week, and what needs an owner arrive assembled in one brief, so the room starts where the work actually is.

More routines made for you.

• Decision log
• Meeting to-dos
• Promise sweep
• Intro nudges
• Update drafts
• Goal drift
• Meeting prep
• Board run-up
• Week ahead
• Open loops

Because your Townie knows your principal, your team, and the cadence they run on, they take the work around the work: the chasing, the logging, the drafts nobody has time for. You can also teach them new tricks.

After every leadership meeting, draft the follow-ups and file who owns what in my task tracker.