HappyCEO Build Log

The Initial Vision

What the User Said (Voice Transcription)

The project started with a voice-to-text message that was somewhat rough:

"You are the co CEO of Happy Operators... the first task is to make sure that our website is kept up to date. If I give you requests such as update the website... you're able to do that via a sub agent... I want to send an email to all our customers. So our customers live inside Notion... Maybe it could be a command or a skill I don't know at this point... I want to go okay we're sending January email and you need to look at our recent activity on LinkedIn on our Slack..."

Distilled Requirements

From this, I extracted three core capabilities:

1. Website Updates - Edit and deploy website changes
2. Monthly Customer Emails - Aggregate data from multiple sources and send emails
3. Persistent Context - A persona file so Claude "remembers" the company context

Lesson: Voice transcriptions are messy. Your job is to extract the intent and requirements, not get hung up on transcription errors.

Discovery Phase

Step 1: Explore What Exists

Action: Used the Task tool with subagent_type=Explore to scan the /Users/matt/Code/HappyCEO directory.

Finding: The directory was completely empty - a fresh start.

Why This Matters: Always explore before building. Don't assume. The exploration agent is designed for this - it's faster and more thorough than manual file-by-file searching.

Step 2: Ask Clarifying Questions

Tool Used: AskUserQuestion - Claude Code's built-in tool for structured questions.

Questions Asked:

1. Where does your company website live? → Separate Git repo at /Users/matt/Code/happyopsv2
2. How do you want to trigger the monthly email workflow? → Slash command (recommended)
3. For sending emails, what service do you use? → Not sure yet
4. Do you have MCP servers set up for any services? → None yet
5. What does Happy Operators do? → AI training & transformation for founders and teams
6. Who are your customers? → Both B2B and B2C

Why This Pattern: Rather than guessing or making assumptions, structured questions give users clear choices, document decisions for later reference, and prevent rework from misunderstandings.

Step 3: Explore Connected Systems

Action: Explored the happyopsv2 website repo to understand:

• Tech stack: Astro 5.0
• Content structure: Markdown collections in src/content/
• Deployment: Vercel (auto-deploys on push)

Content Locations Discovered:

Why This Matters: Understanding the existing system architecture determines what's possible. Astro + Vercel means simple Git-based updates work perfectly.

Architecture Decisions

Decision 1: Project Structure

/Users/matt/Code/HappyCEO/
├── PERSONA.md          # Co-CEO role & company context
├── CLAUDE.md           # Instructions for Claude Code
├── CHANGELOG.md        # This file - process documentation
├── skills/             # Custom slash commands
│   └── monthly-email.md
├── templates/          # Reusable templates
│   └── monthly-roundup.md
└── data/               # Working files, caches

Why This Structure:

1. PERSONA.md - Central source of truth for company context
2. CLAUDE.md - Claude Code looks for this file automatically
3. skills/ - Claude Code supports custom slash commands via markdown files
4. templates/ - Separating templates keeps things modular
5. data/ - A place for working files, keeps the root clean

Decision 2: Slash Command vs Other Approaches

Options Considered:

1. Natural language ("Send January email")
2. Slash command (/monthly-email) ← Chosen
3. External trigger (n8n webhook, cron job)

Reasoning:

• Discoverability - User can type / to see available commands
• Consistency - Same workflow every time
• Documentation - The skill file itself documents the workflow
• Flexibility - Still supports natural variations

Decision 3: Data Sources Strategy

Problem: Multiple data sources with different accessibility levels.

Solution: Hybrid approach:

• Automated: Blog posts, use cases (direct repo access)
• Interactive: LinkedIn highlights, Slack updates (ask the user)
• Future MCP: Notion, Luma (when configured)

Why This Works: Ship something useful now, enhance later. Don't block on perfect integration.

Decision 4: Email Service

Chosen: Resend (to be configured)

Reasoning: Simple API, good deliverability, affordable for small volumes.

Implementation

File 1: PERSONA.md

Purpose: Give Claude persistent context about the company and its role.

Key Sections:

• Role Definition (what the Co-CEO can do)
• Company Overview (what Happy Operators does)
• Key Systems (tools and access)
• Decision Authority (boundaries)
• Communication Style

Design Choice: Keep it scannable with headers and bullet points.

File 2: CLAUDE.md

Purpose: Project-specific instructions that Claude Code automatically loads.

Key Sections:

• Project overview
• Cross-repo workflow (HappyCEO + happyopsv2)
• Available skills
• Integration notes
• Common tasks

Design Choice: Focus on how to work in this project, not company details.

File 3: skills/monthly-email.md

Purpose: Define the /monthly-email slash command workflow.

Key Design Choices:

1. Frontmatter with description - Claude Code uses this for the skill list
2. Numbered steps - Clear sequence for Claude to follow
3. Interactive checkpoints - Uses AskUserQuestion for info Claude can't access
4. Template reference - Points to separate template file
5. Review gate - Always shows draft before sending

File 4: templates/monthly-roundup.md

Purpose: Consistent email format for monthly roundups.

Structure: Greeting, highlights, content sections, CTA, footer.

Design Choice: Use placeholders like {{recent_posts}} that get filled during composition.

Key Lessons

Lesson 1: Start with Questions, Not Assumptions

The initial voice message was ambiguous. Instead of guessing, use AskUserQuestion to clarify the tech stack, understand user preferences, and discover system boundaries.

Takeaway: Structured questions save hours of rework.

Lesson 2: Explore Before Building

Use the Explore agent to understand the empty HappyCEO directory (fresh start) and the happyopsv2 website structure (Astro + Markdown).

Takeaway: 5 minutes of exploration prevents building the wrong thing.

Lesson 3: Hybrid Automation is Realistic

Perfect automation requires API access (often limited or expensive), MCP server setup (time investment), and maintained integrations (ongoing work).

Hybrid approach: Automate what's easy (file access), ask for what's hard (LinkedIn, Slack highlights), add MCP integrations incrementally.

Takeaway: Ship 80% automation now, iterate to 95% later.

Lesson 4: Separation of Concerns

• PERSONA.md = Who (company context)
• CLAUDE.md = How (project instructions)
• skills/ = What (specific workflows)
• templates/ = Format (reusable structures)

Takeaway: Modular structure makes updates easier and keeps files focused.

Lesson 5: Skills > Natural Language for Repeatable Tasks

While Claude understands "send the monthly email," a skill provides consistent execution, self-documentation, discoverability, and versioned workflow.

Takeaway: If you'll do it more than twice, make it a skill.

Lesson 6: Plan Mode for Complex Projects

This project used Claude Code's Plan Mode: entered plan mode to think through architecture, explored codebases without making changes, documented decisions, got user approval before implementing.

Takeaway: Plan mode prevents wasted effort on wrong approaches.

Session Log

Below is the detailed session-by-session log of building HappyCEO. Each entry includes changes made, decisions taken, and notes for future reference.