monthly-investor-updates

name	Monthly Investor Updates
description	This skill should be used when the user asks to "write an investor update", "draft monthly update", "send investor email", "create investor newsletter", "prepare investor communication", or mentions monthly updates, investor emails, LP updates, or stakeholder communication for a VC-backed startup.
version	0.1.0

Monthly Investor Updates

Guidance for helping VC-backed startup CEOs write effective monthly investor updates that build trust, keep investors informed, and create opportunities for help.

Overview

Monthly investor updates are a critical communication channel between board meetings. Effective updates:

• Build trust through consistent communication
• Keep investors engaged and informed
• Create natural opportunities for asks
• Document company progress over time
• Take less than 3 minutes to read

Update Philosophy

Why Monthly Updates Matter

1. Trust building - Consistent updates, even with bad news, build credibility
2. Investor leverage - Informed investors can help more effectively
3. Accountability - Regular cadence creates natural reflection points
4. Documentation - Creates a record of company journey

Common Mistakes to Avoid

1. Too long - Investors are busy; respect their time
2. Too vague - "Things are going well" says nothing
3. No asks - Missed opportunity for investor help
4. Inconsistent - Skipping months erodes trust
5. Defensive tone - Own challenges, don't make excuses

Update Structure

1. Subject Line

Format: [Company Name] Monthly Update - [Month Year]

Examples:

• Acme Corp Monthly Update - January 2024
• Acme Corp: January Update (ARR hit $2M!)

Keep it simple and consistent. Add a hook only for major news.

2. TL;DR Section

Start with 2-3 bullets summarizing the most important news. Investors who only read this section should get the key picture.

Good TL;DR:

TL;DR:
• Hit $2M ARR milestone (+15% MoM)
• Closed our largest deal ever ($150K ACV with Acme Inc)
• Runway extended to 18 months after burn reduction

Bad TL;DR:

TL;DR:
• Things are going well
• We're making progress
• Team is working hard

3. Highlights Section

3-5 specific wins and milestones. Include:

• Revenue wins (deals closed, ARR milestones)
• Product launches or major features
• Key hires
• Partnerships or press
• Customer success stories

Be specific:

• Good: "Closed Acme Inc for $150K ACV, our largest deal ever"
• Bad: "Closed some big deals this month"

4. Metrics Snapshot

Keep it lighter than board reporting. Focus on:

Always include:

• ARR or MRR + growth rate
• Runway

Include 1-2 if notable:

• New customers
• Key product metric
• NRR (if strong)

Format for scanning:

📊 Quick Numbers
• ARR: $2.4M (+12% MoM)
• Runway: 16 months
• New customers: 8

5. Challenges Section

Be transparent but constructive. For each challenge:

• Acknowledge it clearly
• Explain what you're doing about it
• Avoid being defensive

Good challenge framing:

Challenges:
Enterprise sales cycle lengthening (now 12 weeks vs 8).
We're addressing this by adding a solutions engineer to help
with technical evaluations and creating ROI calculators.

6. Asks Section

The most underutilized section. Always include 1-3 specific asks:

Types of asks:

• Introductions to specific companies or people
• Advice on specific decisions
• Candidate referrals for open roles
• Customer introductions in target segments

Good asks:

Asks:
1. Intro to [Specific Person] at [Company] - they're in our
   target segment and [Investor Name] knows them
2. Advice on international expansion timing - considering
   UK office in Q3

Bad asks:

Asks:
• Let us know if you can help with anything
• Introductions always welcome

7. Looking Ahead

1-2 priorities for the coming month:

Looking Ahead:
• Launch self-serve tier (targeting Feb 15)
• Close 2 enterprise deals in pipeline ($200K total)

Tone and Style

Voice

• Conversational - Write like you're updating a supportive friend
• Confident - Own your progress without overselling
• Transparent - Acknowledge difficulties honestly
• Specific - Data and examples over generalities
• Grateful - Thank investors for specific help, but don't overdo it

Length

Target 300-500 words for the main body. Investors should be able to read it in 2-3 minutes.

Formatting

• Use bullet points for scannability
• Bold key numbers and milestones
• Keep paragraphs short (2-3 sentences)
• Use consistent structure month to month

Configuration (Optional)

This plugin works standalone without any configuration. When config is needed, check in this order:

• .claude/investor-updates.local.md (plugin's own config)
• .claude/metrics.local.md (if using metrics plugin)
• .claude/board-prep.local.md (if using board-prep plugin)

If no config exists, ask the user for:

• Company name and stage
• Current metrics (ARR/MRR, growth, runway)
• Investor/board member list (for recipient suggestions)

Additional Resources

Reference Files

For detailed guidance, consult:

• references/email-templates.md - Ready-to-use email templates
• references/metrics-formatting.md - How to present metrics

Example Files

Working examples in examples/:

• examples/good-month-update.md - Strong performance update
• examples/tough-month-update.md - Update with challenges
• examples/milestone-update.md - Major milestone announcement