Your Digital Chief of Staff
Pepper handles your email, calendar, meetings, and relationships — so you can focus on what actually moves the needle.
Replace 60–90 minutes of daily inbox time with a 2-minute briefing.
Try it for free. No credit card.
14-day EA trial included — full capabilities from day one
Sound familiar?
The higher you rise, the more you're buried in operational overhead. Pepper solves this at the root.
Drowning in communication
200+ emails before lunch. Scheduling a single meeting takes 4-6 exchanges. Follow-ups slip through the cracks because there's no system connecting it all.
Walking into meetings blind
Context is scattered across email, calendar, Slack, and memory. What do you owe them? What did they promise you last time? Good luck finding out in two minutes.
Everything slips through the cracks
Tasks scattered across five apps. Commitments untracked. Relationships going cold because there's no system to surface "it's been 3 weeks since you talked to Marcus."
Briefings, Not Inboxes
Pepper replaces the inbox paradigm entirely. Instead of wading through hundreds of messages, you get a curated morning briefing covering everything that needs your attention — email, calendar, meetings, tasks, and relationships.
Every item is analyzed, prioritized, and presented as an actionable decision card. You approve, edit, or skip with one tap. Pepper handles the rest.
See how it worksMorning Briefing
Tuesday, Feb 5
Sarah Chen · Term sheet follow-up
94% confidence
Everything a great Chief of Staff does
Six pillars of executive operations — modeled on how elite human EAs actually work. Each one is powerful alone. Together, they compound.
Email Intelligence
Classification, smart triage, and drafts that sound like you — adapted per recipient. VIP emails always surface first.
Feeds into → Meeting Prep, Relationship Profiles
Calendar Intelligence
Strategic scheduling, focus time protection, and task blocking. Your calendar becomes a tool for protecting what matters.
Feeds into → Task Scheduling, Focus Time Audits
Meeting Intelligence
Walk into every meeting prepared with relationship context, open commitments, and talking points. Walk out with captured action items.
Feeds into → Commitment Tracking, Relationship Context
Task Intelligence
Auto-extracted from emails and meetings. Scheduled on your calendar. A unified "Waiting On" view tracks what others owe you.
Feeds into → Calendar Blocking, Follow-up Drafts
Relationship Intelligence
Never let an important relationship go cold. Searchable profiles built from every interaction. Health monitoring that tells you when it's been too long.
Try asking:
"Who in my network invests in seed-stage healthcare?"
Feeds into → Meeting Prep, Proactive Check-ins
Proactive Intelligence
Pepper notices what you'd miss and flags it before it becomes a problem. Delegate by voice or text — "Hey Pepper, follow up with Marcus about the partnership" — and it executes with full context.
Feeds into → Everything. This is the pinnacle.
Compounding intelligence
Every email enriches your meeting prep. Every meeting note deepens your relationship profiles. Every completed task sharpens Pepper's ability to anticipate what's next.
Week 1: Pepper learns your patterns. Month 1: Pepper anticipates your needs. Month 3: Pepper runs your operations while you focus on strategy.
Built on how the best human EAs actually work
Pepper was designed by studying how world-class Executive Assistants and Chiefs of Staff operate — then building AI that replicates those proven practices at scale.
Briefings over raw feeds
The best EAs brief you on what happened and what needs you. They don't hand you a stack of mail.
Anticipation over reaction
The #1 valued trait of elite EAs is seeing what's coming and preparing for it before you ask.
Calendar as strategy
Great EAs protect your time and guard your focus blocks. They treat scheduling as strategic capacity protection.
Earned trust through proof
You wouldn't give a new hire your most sensitive communications on day one. Pepper works the same way.
Pepper earns your trust
Pepper starts as an Intern — observing and learning. As it proves its judgment, you promote it. Each level unlocks more autonomy.
A career ladder built on proven competence. Progressive trust, at your pace.
Intern
Free
Observes and learns. Shows you what it would do. Organizes your inbox, delivers briefings.
Assistant
$49/mo
Creates drafts, proposes calendar events, captures meeting notes. Everything needs your approval.
Executive Assistant
$99/mo
Handles routine with a countdown timer. Full meeting prep. Task extraction and calendar blocking. You manage exceptions.
Senior EA
$199/mo
Delegates by voice. Proactive follow-ups. Tell Pepper what to do in natural language and it executes with full context.
Chief of Staff
$299/mo
Anticipates needs. Searchable relationship intelligence. Operates autonomously within earned boundaries. You see exceptions only.
5–10 hrs
Saved per week
<2 min
Briefing replaces 60–90 min inbox
6 pillars
Connected and compounding
From $49
vs. $4,000+/mo for a human EA
From signup to first briefing in minutes
Three steps. No setup wizards. No configuration.
Connect Gmail
One-click Google OAuth. Read-only by default.
Get your first briefing
Pepper analyzes your inbox and calendar in under 2 minutes.
Watch Pepper learn
Over the first week, Pepper maps your VIPs, style, and patterns.
Ready to meet your new Chief of Staff?
Start with full EA capabilities for 14 days. No credit card.