Frequently asked questions

Startup CEOs at Series A stage (10–50 employees) who receive 50+ emails per day, use Gmail and Slack, respond to email themselves (no executive assistant), and lead remote or hybrid teams. If your most important conversations happen in written channels — email, Slack, calendar — the AI has near-complete context and the product is transformative.

If you use Outlook or Microsoft 365 for email, we can't connect yet — it's on our roadmap. If you receive fewer than 20 emails a day, inbox triage isn't your bottleneck and the core feature won't save you meaningful time. If most of your communication happens by phone or in-person, the AI won't have enough context to be accurate.

No. Email and calendar are the core. Slack significantly enriches the AI's context — investor DMs, customer channels, team updates all feed into smarter classification and richer morning briefs — but the product works well without it.

Different jobs. A human executive assistant (EA) handles scheduling, logistics, and relationship maintenance. Chief of Staff handles classification, drafting, strategic reflection, and relationship decay detection. They complement each other — think of it as giving your EA a copilot, not replacing them.

Never without your approval. The AI drafts replies — you review, edit, and approve. Every action has a 5-second undo window. Nothing auto-sends. Full audit trail of every decision.

Every time you edit a draft, the AI learns from the difference between what it wrote and what you changed it to. In week 1, you'll rewrite most drafts. By week 4, the rewrite rate drops to 30–40%. By month 3, the AI handles 85%+ of routine communication in your voice. The key: edit drafts rather than deleting them — each edit teaches the model.

A daily digest delivered before your first meeting. It summarizes overnight activity across email and Slack, prepares talking points for each meeting with attendee context, and flags people who need your attention. It's designed to replace opening Gmail, Slack, and Google Calendar separately.

A weekly reflection delivered Sunday evening. It analyzes where your time actually went — what you approved, rejected, and ignored — and compares it to your stated strategic goals. If you said fundraising is priority #1 but spent 60% of your time on product, Zenmaster tells you. It's the accountability partner most CEOs don't have.

It monitors your communication patterns with key contacts — investors, customers, board members, candidates — and flags when relationships are going cold before you notice. If you haven't responded to an important investor in 8 days, you'll know. If a key customer has gone quiet, you'll see it. It's the follow-up you forgot you needed to send.

The AI processes your messages to classify and draft. No human at Chief of Staff reads your email. OAuth tokens are encrypted at rest. You can disconnect any channel at any time and all associated data is deleted.

Currently, the AI reads all your connected emails to provide accurate classification and context. Excluding specific threads is not yet supported. That said, everything stays between you and the AI — no human at Chief of Staff sees your email, and drafts are only ever sent with your explicit approval.

Your data is stored on encrypted infrastructure in the EU (eu-central-1). We are GDPR-compliant with a full Record of Processing Activities and Data Processing Agreements with all sub-processors. See our Privacy Policy for details.

Starter — $49/mo
Gmail, AI triage, morning brief, voice learning.

Pro — $149/mo
Everything in Starter + Slack, calendar, goals, Zenmaster.

Executive — $299/mo
Everything in Pro + team delegation, custom AI agents, CRM integration.

All Pro features are free during the beta.

Under 5 minutes. Connect your Gmail via OAuth, have a brief conversation with the AI about your business and goals, and your first prioritized inbox appears within minutes. No configuration, no workflow building, no technical setup.

Day 1 — Inbox classification saves time immediately.
Week 1 — Relationship tracking and goal alignment kick in.
Week 4 — Your first Zenmaster reflection. The voice model is noticeably better.
Month 3 — Full compound value. All features reinforcing each other.

The critical period is weeks 1–4. Edit drafts, set goals, and the product improves dramatically.

Not yet. This is our most-requested integration and it's on the roadmap. If your company uses Microsoft 365 for email, Chief of Staff can't connect to your inbox today. We'll announce Outlook support when it's ready.

Not yet. Slack is our current messaging integration. Teams support is planned alongside the Microsoft 365 integration.

The AI works best in English. It won't crash on other languages, but classification accuracy and draft quality decrease significantly for non-English communication. If your primary business language isn't English, you'll get a degraded experience today.

Not yet. CRM integration is planned for the Executive tier. Today, the relationship tracker works from email and calendar data — which covers most CEO-level relationship management. Deep CRM integration will add deal context and pipeline data.