ChiefOS

Company brain for AI-native execution.

ChiefOS connects Gmail, Calendar, Slack, and the tools your company runs on. Every morning before 7am, it delivers a structured Executive Brief: what changed, what is slipping, who owns it, and what needs a decision.

What the product does

ChiefOS builds a live Execution Graph from your connected tools. Every objective, owner, open thread, risk, decision, and commitment is structured and connected. The Executive Brief pulls from this graph every morning to surface exactly what the founder needs to know, decide, fix, unblock, or do that day.

The product is not a dashboard. It is an execution layer. The brief earns trust in the first week. The graph gets smarter over time.

Integrations

Gmail — inbox context, open threads, stalled commitments
Google Calendar — meeting prep, deadline tracking, calendar risk
Slack — team signals, open threads, decision tracking
Linear — engineering issues and project status
HubSpot — CRM activity, deal pipeline, customer signals
Notion — pages, docs, and company context

Integrations are read-first by default. ChiefOS never posts, sends, or modifies data without your explicit approval.

Google access

Gmail read access for context and thread analysis
Gmail compose access for draft creation only
Google Calendar read access for meeting and deadline context
Google Calendar events access for tentative internal event creation only
Basic Google profile access for account identity

Safety model

ChiefOS does not send email, RSVP to calendar invites, post Slack messages, or modify any connected system on your behalf. When draft or tentative event features are enabled, they are review-first and require explicit approval before anything is sent or created.

Pilot

ChiefOS is available as a 90-day pilot. $5,000 for the first 90 days, then $2,500/month. Setup takes 15 minutes. Your first brief arrives the next morning.

Start a pilot · Book a 15-min call

Policies

Built by Steven Callaway. steven@getchiefos.com