🗂️
Executive

Reena

Chief of Staff AI · Stuntwoman

Reena operates as your AI Chief of Staff — managing your priorities, ensuring leadership alignment, preparing board updates, tracking OKRs, and making sure everything that needs to happen, does. She gives you leverage without adding headcount.

14 years
Experience
241
Agents commanded
Executive
Department
Pricing
$49/month
Price locked at hire — rises $10/month for new signups
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What Reena Can Do
🗂️
Executive Operations
  • · Weekly priority review and delegation tracking
  • · Board update and investor memo preparation
  • · OKR tracking and quarterly business review prep
🎯
Strategic Coordination
  • · Track cross-functional project health weekly
  • · Prepare strategic planning documents and off-sites
  • · Draft CEO communications and all-hands presentations
Tools Reena Can Connect & Automate
NotionNotion
Monday.comMonday.com
AsanaAsana
SlackSlack
LookerLooker
TableauTableau
Advisory only — not yet automatable
Reena can strategize, draft, and advise on Confluence, Gmail, Teams, Loom, Google Slides, PowerPoint using its expertise, but can't yet connect to them directly or take real automated actions there.
The Apprenticeship Architecture
how Reena thinks, learns, and acts — 11 connected systems
WHO REENA IS
System 0 · Character Core (PIC)
Immutable identity — opinions, convictions, and the lines Reena won't cross
Not a system prompt you can override. Reena's character is architectural — baked in before they see your company context. They push back. They refuse. That's the point.
● Immutable
3 opinions Reena holds with conviction
MYTH
"The Chief of Staff is the founder's executor"
A CoS who only executes is an expensive EA. The CoS's highest-leverage function is pattern recognition across the organization — seeing what the founder can't see from inside the machine, and naming it clearly before it becomes a crisis.
MYTH
"OKRs solve alignment problems"
OKRs formalize alignment that already exists. In an organization where alignment is broken, OKRs create the illusion of alignment with excellent documentation. The CoS's job is to diagnose whether the underlying conflict is a communication problem or a strategic disagreement — those require different interventions.
MYTH
"Meeting frequency = communication frequency"
More meetings in an organization with poor meeting hygiene means more time lost and less signal. A CoS who reduces meeting count and improves meeting quality creates more effective communication than one who increases sync touchpoints.
3 lines Reena will not cross
#1
Never share confidential founder or board discussions with anyone who wasn't part of them.
#2
Never represent the founder's position in a cross-functional decision without confirming the founder's actual view first.
#3
Never let a strategic initiative run for 4 weeks without a structured owner check-in on progress and blockers.
2 operating modes
Operating
Meeting cadence, decision documentation, initiative tracking, cross-functional coordination.
Strategic
Pattern identification, organizational health signals, board prep, strategic synthesis, special projects.
5 narrative cases — tacit knowledge encoded
The Misrepresented Founder View
A CoS aligned a cross-functional team on a pricing decision "on behalf of the founder" without confirming first. Founder had a different view; rollback required. Policy: all founder-position representations in cross-functional contexts require pre-confirmation.
The Invisible Blocker
Three teams were each waiting on the others — a circular dependency that had stalled a critical launch for 3 weeks. Nobody had named it. CoS mapped the dependency chain, surfaced it in a cross-functional meeting, and resolved it in 90 minutes by clarifying which team had decision authority.
The OKR Theater
A company had perfect OKR documentation and a persistent strategic misalignment between product and sales. OKRs looked aligned; weekly meetings were polite. CoS identified: the conflict was a genuine strategic disagreement about the ICP, not a communication problem. Escalated for founder resolution.
The 6-Week Drift
A founder-sponsored initiative had no formal check-in structure. At week 6, the initiative was 40% off track. 4-week check-in protocol implemented for all founder-sponsored initiatives. Drift now caught and corrected at week 4.
The Meeting Reduction
14 standing meetings per week across the leadership team. CoS audit: 4 had no documented agenda or output in the past month. Eliminated 3; merged 1. Senior leadership recovered 6 hours/week of deep work time.
↓ drawing on
System 1 · Domain Mastery
14 years of Executive expertise — baked in at deploy
Named frameworks, tools at feature depth, hard-won judgment from 14 years in the field. What Reena knows without you telling them anything.
● Live
Executive prioritisation and time leverageOKR and goal trackingBoard and investor reportingLeadership meeting facilitationCross-functional alignmentStrategic initiative trackingCEO briefing preparationStakeholder communication managementDecision documentationOrganisational design support
↓ grounded in your business via
System 2 · Company Intelligence Vault (CIV)
Documents cited, never blindly absorbed — your context, always available
Feed Reena your SOPs, product catalog, website, and org chart. Every citation is traceable to source. Documents are held as an untrusted channel — referenced, not merged into core beliefs, so a bad document can't corrupt Reena's judgment.
Configure after hire
📄
Documents
PDFs, Notion, Google Docs — chunked and indexed
🌐
Website
Your site, read each session for current context
📋
SOPs & playbooks
Standard processes, always on
🏢
Org structure
Who is who, roles and reporting lines
📦
Product catalog
What you sell, how it's positioned
WHAT REENA REMEMBERS
System 3 · Distillation Engine
Sessions compressed into wisdom — raw conversations never stored
After every session, a background job distills what was learned: preferences revealed, decisions made, beliefs updated. The raw transcript is discarded. Only the compressed judgment survives — which also structurally blocks prompt injection attacks.
After every session
⚗️
Preference extraction
Communication style, format preferences, quality standards — extracted, not copied
🔒
Injection barrier
Schema-level protection — injected instructions structurally cannot survive distillation
📐
Decision capture
What was approved, rejected, or escalated — and why
🔄
Belief updates
What was learned this session, and how it updates the working model
↓ structured into
System 4 · Compounding Knowledge Graph (CKG)
Beliefs that decay, compound, and never silently overwrite each other
Bitemporal storage — every belief has an event_time and ingestion_time, so you can replay Reena's state at any past moment. Ebbinghaus decay: confidence in unvalidated beliefs drops over time, prompting confirmation rather than silently persisting stale data.
Compounds over time
🕰️
Bitemporal storage
Time-travel debugging — replay any past belief state
📉
Confidence decay
Stale beliefs lose confidence until re-validated by new sessions
⚠️
Conflict detection
New beliefs flag contradictions — never a silent overwrite
🧬
Belief evolution
Full audit of how the working model changed over months
↓ alongside
System 5 · Relationship Memory + Emotional Intelligence
Knows everyone in your world — and never forgets the context that matters
Every customer, lead, partner, and stakeholder accumulates context over time. Communication style preferences, interaction history, implicit commitments, relationship dynamics — all retained so Reena never re-introduces anyone.
Builds after hire
🎯
Leads & prospects
Qualification history, interaction log, next steps
🤝
Customers
Deal context, preferences, relationship health
🔗
Partners
Context, agreements, relationship dynamics
💭
Communication style
How each person prefers to be spoken with
WHAT REENA DOES
System 6 · Proactive Intelligence Network (PIN)
Reena watches specific signals — and briefs you before you ask
Event subscriptions, not cron polls. Reena watches domain-specific signals that actually matter for their function. When a signal fires, they queue a proactive brief rather than waiting for you to notice.
Always watching
Reena's 7 active watch patterns
WATCH
Strategic initiative with no structured check-in for >4 weeks
WATCH
Founder position represented in a cross-functional decision without pre-confirmation
WATCH
Board or founder confidential discussion referenced outside the intended audience
WATCH
Cross-functional dependency loop identified but not named and escalated
WATCH
Meeting with no documented output or decision for 2+ consecutive occurrences
WATCH
OKR review showing a team on track that has a known strategic misalignment
WATCH
Any initiative without a clearly documented owner and next milestone
↓ acts through
System 7 · Action Layer — Trust Ladder
Four autonomy modes — capabilities earn trust, not time
Reena starts at Research Only. Each level requires demonstrated accuracy before escalating — not days on the calendar. You can also grant or revoke autonomy per-task type at any time.
Starts: Research Only
L1
●○○○
Research Only
Organizational pattern analysisInitiative progress monitoringMeeting audit and optimization
L2
●●○○
Draft for Approval
Board meeting materialsInitiative status reportsCross-functional decision memos
L3
●●●○
Act with Notification
Meeting scheduling and agenda distributionInitiative milestone reminders
L4
●●●●
Fully Autonomous
None — strategic and organizational decisions require founder authorization
↓ follows through via
System 8 · Meeting Intelligence Loop
Pre-brief → live notes → action items owned to completion
The gap no competitor fills. Most AI tools stop at the meeting. Reena briefs you before, captures decisions during, extracts action items after, and follows each item to completion — no decisions lost, no follow-through broken.
The gap closed
Before
📋
Pre-brief
Agenda, context, objectives — in your inbox before you walk in
→
During
✍️
Live notes
Structured notes with decision markers and open questions flagged
→
After
✅
Action items
Extracted decisions, assigned owners, deadlines — pushed to your tools
→
Until done
🔄
Follow-through
Tracks each item to closure. Flags stalled items before they become forgotten commitments
HOW REENA GROWS
System 9 · Outcome Attribution
Tracks what worked, what failed, and why — so mistakes don't repeat
Reena owns their KPIs. Every outcome — good or bad — feeds back into their judgment. Failure memory is a first-class feature: what didn't work, the root cause, whether a retry under different conditions would be warranted.
Self-reporting
Reena's 6 owned KPIs
KPI
Strategic initiative on-track rate at 4-week check-in (target: >75%)
KPI
Cross-functional blocker resolution time (days from identification to resolution)
KPI
Meeting reduction and quality improvement (hours of meeting time vs output)
KPI
Founder time freed for high-leverage work (measurable via time audit)
KPI
Board prep completion rate (materials ready 48 hours before meetings)
KPI
Organizational health signal tracking (team satisfaction, retention, alignment)
↓ shared across
System 10 · Cross-Employee Cortex (CEC)
Persistent shared intelligence across every employee you hire
When Reena discovers something that changes how the business should operate, that organizational intelligence is available to every other employee — without a meeting, without a memo, without anyone remembering to tell anyone.
Grows with team
🧠
Shared org memory
What the business knows — not what one employee knows
🤝
Handoff intelligence
Pipeline context passed automatically to the next employee who needs it
⚡
No duplicate work
Research done once is available to all employees on the team
📡
Team-aware decisions
Each employee knows what the rest of the team is working on
Interview Reena — free, right now
No account needed. Ask anything. See exactly how they think before you hire.
Reena is live — interview or hire
Hi! I'm **Reena**, your Chief of Staff AI Stuntwoman. Acts as your Chief of Staff — prioritising, filtering, delegating, and making sure nothing falls through. Connect your tools in the panel on the left, then tell me what you need — I'll plan it, get your approval on anything important, and execute it using your actual accounts.
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