Rey Columna
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Concept

Sasshi

AI chief of staff · iPhone

Every other tool shows you what's in front of you. Sasshi shows you what you're missing. Its AI, Scout, reads your work and each morning tells you what nobody is saying.

Request early accessInvite only. A small group of engineering leaders goes first.

Status
Concept, in design
Role
Product, design & architecture
For
CTOs, VPs & engineering managers
Platform
iPhone
Access
Early access list
iPhone lock screen at 7:30 with a Sasshi notification: 4 blind spots today, one is urgent: payments incidents
Sign-in screen with the Sasshi mark, a dial of four slices with one in orange: what your calendar, inbox and boards aren't telling you

7:30 AM. One notification, then the dial fills with the day's blind spots. Design mockups, not a released app. Sample data and made-up names.

The problem

Engineering leaders live in six tools at once: calendar, email, Slack, meetings, project boards and code. Each one shows what's in front of you. None of them shows what's missing.

The things that hurt are the ones nobody says out loud. A team you haven't talked to in three weeks. Two teams building the same thing. A decision made on a call and never written down. A risk that keeps growing because nobody wants to raise it first.

How it works

Scout reads your tools, read-only. Every morning at 7:30 it surfaces 3 to 5 blind spots, in four kinds.

People gaps

Teams and people who've gone quiet on you, especially when their work is slipping.

Duplicate work

Two teams building the same thing in two repos, with no shared thread.

Undocumented decisions

A call that changed direction and left no doc, ticket or message behind.

Silent risks

A problem growing in the data that never comes up in your meetings.

Every blind spot comes with:

  • Receipts. The exact messages, meetings and tickets it came from.
  • Why it matters, in a sentence or two.
  • A confidence level, so you know how hard to lean on it.
  • A one-tap next step: a drafted message, a 15-minute booking, or a decision record.

Nothing is sent without you. Scout drafts. You read it, edit it, and send it from your own Slack or Mail.

Key screens

The daily loop, from the morning list to a handled blind spot.

Today: a dial showing 4 blind spots with only the urgent silent-risk slice in orange, then the urgent card: payments incidents are up 4x this month
Today. A watch-style dial, one slice per blind spot. Only the urgent one is in color.
Blind spot detail under a blue People header: 23 days since you last talked to the Mobile team against a usual gap of 7 to 12, why it matters, a chart of days between contacts, and the evidence
A blind spot, with the receipts behind it. The header takes the color of its type.
Drafted check-in to Teo, the Mobile lead, in Slack, with Direct, Warm and Brief tone options and the sources Scout used
The next step, drafted. Pick a tone, edit, send it yourself.
The Map in light mode: a grey heat grid of contact with each team over six weeks, gone-cold weeks hatched, and a Going cold list
The Map, in light mode. Who's gone cold, team by team.

In motion

Every move shows where something came from or where it went. Each one has a calm version for Reduce Motion.

The gap chart draws itself, then the evidence lands in order.

Send hands off to Slack. The text is copied, ready to paste.

Mark a card as not a blind spot, give a reason, and Scout learns from it.

Making it a habit

The first version worked but felt flat. So each day got a finish line and each week got a look back. No points, no leaderboards, no confetti. The best day is the one you spend the least time in the app.

Clear your dial

Act on every blind spot and the dial closes. Then Scout stays quiet until tomorrow.

Your week recap: 3 saves, dial clear 4 of 5 days, Radar 75, and each save with its sources

Your week

Every Friday: what you caught early and what happened after, with receipts. One tap copies it as an update.

The Radar

A private weekly reading, 0 to 100, of how clear your view of the org is, and which habit would sharpen it.

Built for the bad mornings

Scans run late. Payments fail. You clear the wrong card. When something goes wrong, Sasshi says what happened, what Scout is doing about it, and the one thing you can do. When it matters, a real person is one tap away.

Today at 7:36: your brief is running late, ready by 9:00 AM. Scout is trying again every 15 minutes and will send a notification. Nothing to do. Yesterday's list is below.
Running late. Ready by 9:00, with nothing for you to do. Yesterday's list stays up.
Today with 2 of 4 left: the Mobile check-in reads Handed off to Slack at 7:45 AM with a Not sent? Reopen link, and a Cleared. Undo toast with a countdown
Honest hand-offs. It says "Handed off to Slack," never "Sent." Cleared the wrong one? Undo.
Help screen: Stuck, or something looks off? A Talk to a person button that emails Rey, a real reply within one business day, and a note that nothing about your blind spots is attached
Talk to a person. A real reply within one business day.
Today after a failed payment: update payment to get tomorrow's brief. Scout is paused and nothing is deleted. Yesterday's brief below, read-only, with a locked dial
Payment failed. Scout pauses, nothing is deleted, and yesterday's brief stays readable.

Under the hood

Built so a skeptical CTO would trust it with their inbox.

  • Native SwiftUI on iPhone, with VoiceOver and Reduce Motion on every screen.
  • Backend on Google Cloud. Scout scans early each morning, so the list is ready at 7:30.
  • Read-only access to every source. Nothing leaves the app unless you send it.
  • Raw messages aren't stored. Scout keeps who, when and what, plus short quotes as receipts, then deletes them after 30 days by default.
  • Your data never trains an AI model. Delete your account in two taps and it's gone.

Want in early?

Sasshi is in design. Leave your email and I'll invite a small group of engineering leaders first.

Email me for early access

Only used to contact you about Sasshi. No spam, no sharing. Ask me to delete it anytime.

Questions

Is Sasshi available?

No. Sasshi is a concept in design. There is no app to download yet.

What does Sasshi do?

Its AI, Scout, reads your tools, read-only. Every morning at 7:30 it surfaces 3 to 5 blind spots: people gaps, duplicate work, undocumented decisions and silent risks. Each one comes with receipts and a one-tap next step.

Does Scout send messages for me?

No. Scout drafts. You read it, edit it, and send it from your own Slack or Mail.

Guides

Practical how-tos on the problems Sasshi is built for. All guides

A concept in design. No app to download yet.