Founding 100 Pricing—Early adopter rates locked in for your first year.

Prices will increase to standard rates once we reach 100 paid users.

Start free. Upgrade when Pepper earns it.

A career ladder Pepper climbs with you

Pepper earns more responsibility as it proves its judgment across email, calendar, meetings, tasks, relationships, and proactive intelligence. Each tier unlocks capabilities — not arbitrary feature gates.

Intern

Free

Watch and learn

Join Waitlist

Includes

  • Email classification & briefings
  • Ambient dashboard
  • 500 emails / 50 AI actions per month

Assistant

$99standard
$49/mo
Founding rate — locked for your first year

Draft and suggest

Join Waitlist

New at this tier

  • Draft generation & voice matching
  • Meeting context (attendee info)
  • Manual task extraction
  • 2,000 emails / 500 AI actions per month

Executive Assistant

Most Popular
$399standard
$199/mo
Founding rate — locked for your first year

Handle routine, manage exceptions

Join Waitlist

New at this tier

  • Auto-send with countdown timer
  • Smart triage & auto-archive
  • Full meeting prep with talking points
  • 1:1 scheduling & commitment tracking
  • 10,000 emails / 2,000 AI actions per month

Chief of Staff

$599standard
$299/mo
Founding rate — locked for your first year

Anticipate and act

Join Waitlist

New at this tier

  • Relationship intelligence & network search
  • Proactive tasking (anticipation engine)
  • Autonomous swim lanes
  • Post-meeting note flow
  • Unlimited everything

Complete feature comparison

Feature
Intern
(Free)
Assistant
($49/mo)
EA
($199/mo)
Chief of Staff
($299/mo)
Email Intelligence
Email classification
Smart labels
VIP system
Smart Unsubscribe
Draft generation
Auto-send (countdown)
Reading Digest
Calendar & Meeting Prep
Calendar sync
Home screen day itinerary
Meeting context (attendee info)
Full Meeting Prep (internal)
State of Relationship summary
AI-generated talking points
Meeting purpose inference
1:1 Scheduling
Auto web research (new contacts)
Relationship Context in prep
Post-meeting note flow
Task Intelligence
Task extraction (manual)
Task extraction (auto)
Suggest calendar blocks
Auto calendar blocking
Unified "Waiting On" view
Stale task surfacing
Focus time warnings
Focus time protection suggestions
Auto-protect focus time
Meeting Notes
Integration import
Quick capture (text)
Quick capture (voice)
User task extraction
User tasks → Task system
3rd party commitment tracking
Commitment follow-up prompts
Proactive follow-up drafting
Interaction Modes
Morning Briefing
Status Briefing
User-Initiated Tasking
Voice Mode (Hey Pepper)
Proactive Intelligence
Calendar reminders
Proactive insights
Proactive suggestions
Autonomous execution
Relationship Management
Basic contact profiles
Background profile building
AI-generated Relationship Context
AI-powered network search
Relationship health monitoring
Introduction tracking
Connection to User-Initiated Task
Usage Limits
Emails processed / month5002,00010,000Unlimited
AI actions / month505002,000Unlimited
Voice minutes / monthUnlimited

Try EA-level for 14 days, free

Every new account starts with full Executive Assistant capabilities. Experience auto-send, smart triage, and evening wrap-ups before choosing your tier.

No credit card required.

How Pepper compares

Comparison
Human EA
Pepper (EA tier)
Other AI Tools
Cost
$4,000–8,000/mo
From $49/mo
Free–$199/mo
Availability
9–5, limited hours
24/7
Varies
Onboarding
2–4 weeks
Learn in days
Setup required
Calendar & Briefings
✓
✓
✗
Trust Model
Implicit
Earned
None

Human EA: $4,000–15,000/mo. Pepper EA: $399/mo $199/mo (founding rate)

Frequently asked questions

What is Founding 100 pricing?+

Pepper uses significant AI processing to deliver EA-quality work at every tier. Our first 100 paid users get early adopter pricing — locked in for your first year. After we reach 100 users, prices will increase to standard rates for new signups.

What happens after my first year?+

After your first year at founding rates, your plan renews at standard pricing. By then, Pepper will have a full year of compounding intelligence on your patterns, relationships, and preferences — making it more valuable than the day you started.

Can I downgrade Pepper?+

Yes, demotion is always one click. Pepper never takes action above its current trust level.

What happens when I hit the free tier limit?+

Pepper stops processing new content but preserves everything. Upgrade anytime to resume.

Is there a contract?+

No. Month-to-month. Cancel anytime. Founding pricing is locked in for your first 12 months regardless.

What about annual pricing?+

20% discount on annual plans. Stacks with Founding 100 pricing during your first year.

Can Pepper access my email?+

Pepper uses Gmail API with read-only access by default. Send permissions are only enabled at Assistant tier and above, always with your explicit approval.

What if Pepper makes a mistake?+

Every action has a safety window. Auto-sent emails include a countdown timer. You can always cancel, and Pepper learns from corrections.

How does voice mode work?+

Voice mode (Chief of Staff) lets you interact with Pepper hands-free. Say ‘Hey Pepper’ to start capturing tasks, requesting information, or giving instructions naturally.

What’s included in Relationship Intelligence?+

Chief of Staff tier includes background profiles, AI-generated relationship context, network search, health monitoring, and introduction tracking to keep you informed about your key relationships.

Join the waitlist for early access

Be the first to experience Pepper. We'll reach out when your spot is ready.