Open framework · Built for Claude

Harold.

An adaptive AI architecture that becomes your source of truth.chief of staff.
It learns your business, your rhythm, and your priorities.

Read the Docs Explore the CRM Quick Overview
// TL;DR
🧠
Harold is a system, not a chatbot. It maintains context across sessions and remembers everything.
🔗
Four layers: task management, CRM, operational state files, and a searchable knowledge vault.
⚡
Runs in Claude Code (terminal) or the Claude desktop app. No cloud, no vendor lock-in.
🎯
Not one-size-fits-all. Harold adapts to your workflows, voice-first or keyboard, and customizes itself over time.
📡
Proactive alerts surface stale relationships, overdue tasks, and missed deadlines before you ask.
🤝
Not just orchestration: docs, spreadsheets, financial models, and production-ready apps. Harold built its own CRM and this very page.
Core Systems

Every layer working together.

Harold isn't one tool. It's a stack of interconnected systems that share context, update each other, and surface what matters.

🗄️

Knowledge Vault

Obsidian-based permanent memory. People, companies, meetings, decisions, intel. All linked, all searchable. Harold pulls context from here on every query.

obsidian + mcp
🤝

Relationship CRM

Built by Harold, inside Harold. Iteratively shipped from architecture to production. Warmth scoring, cadence tracking, pipeline stages, and more.

supabase + mcp
🚨

Alerts Engine

Automated monitoring across events, blockers, tasks, and CRM freshness. Ranked by severity and surfaced every morning.

derived alerts
📋

Task Management

Linear integration for project work. Overdue tickets, stale blockers, and sprint progress feed directly into the daily brief.

linear + mcp
📖

Playbooks

Documented procedures for every recurring workflow. Morning brief, meeting debrief, contact intake, investor prep. All standardized, all repeatable.

slash commands
🔬

Model Council

Run strategic questions across multiple LLMs simultaneously. Get consensus maps, conflict analysis, and synthesized verdicts for high-stakes decisions.

multi-llm
Daily Operations

A structured day, not a chatbot.

Harold runs on a rhythm. Morning brief, active sessions, end-of-day capture. Consistent process turns an AI into an actual chief of staff.

☀️
Morning

Daily Brief

Type /morning-brief and Harold reads operational state, runs the alerts engine, and identifies your top priorities, then generates ready-to-run prompts that kick off the day's active sessions.

  • Alerts + blockers review
  • Stale relationship flags
  • Calendar + deadline scan
  • Prioritized action prompts
⚡
Active

Session Work

Each priority from the brief becomes a session. Research, writing, analysis, deal review. Full context from the vault and CRM carries into every task.

  • Vault-grounded research
  • Draft artifacts on demand
  • Log interactions in real time
  • Multi-model analysis
🌙
Close

Session Capture

End every session with /done. Harold writes a structured summary to the vault, updates the CRM, and queues Linear tasks.

  • Key decisions logged
  • Interactions recorded
  • Follow-ups queued
  • Knowledge base updated
Architecture

Four layers.
One coherent system.

Harold's power comes from how the layers talk to each other, not from any single tool.

L1 tasks Work Management Active projects, sprint tasks, blockers, and milestones
LinearMCP
L2 contacts Relationship CRM Relationships, interactions, cadence, pipeline stages, warmth scoring
SupabaseMCP
L3 operations Harold State Files Alerts, blockers, events, facts: real-time operational state
MarkdownJSON
L4 memory Knowledge Vault Deep context: people, companies, decisions, meetings, strategic intel
ObsidianMCP
Live Dashboard

Expedition HQ.

A real-time command center that shows what every agent session is doing right now. No manual reporting: sessions register themselves, and the dashboard paints the picture.

Expedition HQ command center showing eight agents working across research, strategy, writing, coding, data, comms, design, and ops
// LIVE DASHBOARD — 4 sessions, 8 agents active
Eight Agents, One View

Every session lights up.

Each Harold session tracks its own activity across eight categories. Expedition HQ aggregates them into a single live visualization: who's researching, who's coding, who's drafting outreach.

⚡
Auto-detection. Claude Code sessions are detected automatically via JSONL conversation logs. No registration code needed.
📡
Open registration. Any tool can register via a simple JSON file. Not locked to Claude Code.
📋
Multi-session stacking. When multiple sessions use the same agent, the dashboard shows every task, not just the first. One desk, all its workload.
🔍
Archie
Research
🧭
Compass
Strategy
✍️
Quill
Writing
💻
Byte
Coding
📊
Ledger
Data
📨
Mercury
Comms
🎨
Sketch
Design
⚙️
Gears
Ops

Plant the seed.
Let it grow.

Harold is an architecture, not a product. It adapts to your business through use. The docs cover setup, core systems, and patterns to get started. Free, open, yours.

Read the Docs Explore the CRM ← dswinder.xyz
Consultation

Want to talk through your setup?

Harold is open and free, but if you want guidance from the creator, book a 30-minute consultation. Ask questions, explore how it fits your workflow, and if it makes sense, we can even help implement.

$100
30 minutes
Book a Consultation →