AI Chief of Staff for a Flat Team
How we gave a flat marketplace team daily accountability without a management layer: an AI chief of staff that turns the CEO's goals into a personal check-in for every person, twice a day, built on real activity data.
17
Team members get a personal check-in
8am / 5pm
Check-ins in each person's own time zone
10 days
From first request to production
CLIENT OVERVIEW
An online marketplace and live-events company for collectible design, with a lean team across sales, partnerships, listings, and marketing. Revenue depends on input: outreach to buyers and brands, listings published, sellers brought on. The CEO set clear numbers for each role, but the only way to know where anyone stood was to ask, and the answer was usually "good." When the company moved to a flat structure, someone still had to carry the goals to each person every day.
THE PROBLEM
What was broken
Goals lived in emails nobody tracked
Targets were set in email threads and calls, then forgotten. Nobody could say on a given morning what each person was supposed to hit that day, or how far they were from it.
Status meant chasing people
Leadership learned how the week was going by asking. Reports were built by hand when someone had time, so problems showed up after the week was already lost.
A flat team with no management layer
The company removed a layer of people management to stay lean. The reminders, follow-ups, and course corrections that managers used to give had to come from somewhere else.
THE GOALS
What success looks like
Give every team member a personal check-in each weekday morning and evening built from their own goals and work
Let the CEO set goals, priorities, and schedules from the chat assistant the CEO already uses every day
Measure real inputs per role: outreach sent and people reached, brand conversations, listings published, sellers, and sales
Keep each check-in private to the person it's written for, so no team member sees a colleague's email or numbers, and every number traces to its source
OUR APPROACH & SOLUTION
Building a chief of staff that sets the agenda and never invents a number
We wrote and stress-tested the full plan before writing code, including the privacy boundary and the access model. Then we shipped in phases on top of the company's existing admin assistant, with the system running in production 10 days after the request and the first live check-in going out 4 days later.
Phase 1
Roles, Goals, and a Sealed Data Layer
Modeled every team member, their role, and their numbers, editable without a deploy. Work email and calendars flow into a separate, encrypted database area that general tools and staff cannot read.
Phase 2
Goals Learned from Real Conversations
The assistant reads assignments the way a person would. A target only counts when a manager actually set it and sent it, so nobody can set their own easy goal by emailing themselves.
Phase 3
Personal Check-ins, Twice a Day
Every weekday at 8am and 5pm in each person's own time zone, the assistant writes them a check-in: today's top priority, progress against each goal, and the next actions that matter. Every figure is checked in code against real data before the email can send, and a check-in that names a colleague is rejected.
Phase 4
Direction from the CEO's Own Chat Assistant
Connected the system to the CEO's chat assistant with secure sign-in, so the CEO can ask how the team is doing or say "make this week about the chairs sale" and see it in everyone's next check-in. The team lead also gets a Monday and Thursday team recap.
WHAT WE BUILT
Features and capabilities
01
Personal Check-ins Twice a Day
Each of 17 team members gets an email at 8am and 5pm in their own time zone, on weekdays only. It opens with today's top priority, shows two figures for each goal, ranks up to three things that need attention with a next action for each, and lists open items.
02
Drafts Written Ahead of Time
Each check-in is drafted 4 hours before the morning slot and 2 hours before the evening slot, then sent on time. If a draft isn't ready, our team gets an alert instead of the person getting a half-written email.
03
Numbers Checked in Code
Every figure in a check-in must appear in the underlying data, and the code drops any number the AI can't trace. The same checks block verdict words and reject any draft that names a colleague.
04
Goals Read From Manager Email
The system picks up targets and priorities from the email threads where managers set them. A goal only counts when it came from a verified manager's sent mail.
05
Input Metrics per Role
Progress is measured from real activity: outreach sent and recipients reached, brand conversations, listings published, new and returning sellers, sales, marketing growth, and support load. Reach counts people, not only messages, after team feedback showed one send can reach hundreds.
06
Open Asks Tracked
Internal requests that got no answer are logged as open items, so a follow-up doesn't depend on someone remembering it. A request only counts when it appears in the text its sender wrote, not in a quoted reply.
07
Direction From the CEO's Chat Assistant
The CEO can ask how the team is doing, or set goals, priorities, check-in lines, and schedules for one person or the whole team, from the chat assistant the CEO already uses. A company-wide priority needs an end date, so old priorities don't linger.
08
Team Recaps for the Team Lead
Every Monday and Thursday at 8am, the team lead gets each person's goals for the day and the week, with progress this week and last. Listings, sellers, and sales are credited to the person who did the work.
09
A Sealed, Encrypted Data Layer
Work email and calendars are stored encrypted in a separate database area that the company's general admin tools can't read, and stored mail is deleted after 90 days. The boundary is checked while the system runs and fails closed, and sign-in to the chat connector uses OAuth 2.1.
KEY TAKEAWAYS & IMPACT
What changed for this business
17
Team members briefed every morning and evening
Each person starts and ends the workday with their own goals, progress, and next actions in their inbox. Nobody has to ask what matters today.
9
Management actions available from one chat
The CEO sets goals, priorities, check-in notes, and schedules for one person or the whole team in plain language. Access is limited to an allowlist of two accounts, checked on every request, and every action is logged.
10 days
From first request to production
The CEO asked for it on a weekly call, and it was running in production 10 days later, with the plan written and reviewed before any code. The first live check-in went out 4 days after that.
THE OUTCOME
The wins
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Every team member starts and ends each workday knowing their top priority and where they stand, without anyone asking for a status update.
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Progress comes from real activity data instead of self-reported status, and a number the system can't trace to that data never reaches an inbox.
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Team progress that used to come from one-off reports built by hand reaches the team lead every Monday and Thursday.
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Goals can't be quietly rewritten, because only targets a manager set and sent count.
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No team member's check-in shows a colleague's name or numbers; team-wide progress goes to leadership.