UitbreidenOS Portfolio Monitor Skill
When to activate
- Synthesizing monthly or quarterly board update packages from portfolio companies
- Tracking KPIs across multiple portfolio companies and surfacing anomalies
- Preparing for a board meeting and need to identify the key issues to focus on
- Writing portfolio company summaries for LP quarterly reports
- Identifying follow-on investment triggers or companies needing intervention
- Running a portfolio health review before a fund close or LP meeting
When NOT to use
- Real-time financial monitoring that requires live data integrations — this is for periodic review of documents you provide
- Auditing portfolio company financials — that requires an accountant
- Making follow-on investment decisions without full diligence — this skill surfaces signals, not conclusions
Instructions
Single company board update synthesis
Synthesize this board update for a portfolio company. Flag issues, risks, and items requiring my attention.
COMPANY: [name]
PERIOD: [month/quarter]
FUND OWNERSHIP: [X]%
BOARD SEAT: [yes/no — observer/full]
INVESTMENT THESIS (1 sentence): [what we believed when we invested]
BOARD PACKAGE CONTENTS (paste or summarize):
[Paste the board deck summary, management letter, or key slides]
Synthesize into:
1. HEADLINE (2 sentences): Is this company on track, ahead, or behind? What's the one thing I need to know?
2. KPI SCORECARD vs. plan:
| Metric | Plan | Actual | Delta | Status |
|---|---|---|---|---|
| Revenue/ARR | $[X] | $[X] | [+/-X%] | [Green/Yellow/Red] |
| Gross margin | [X]% | [X]% | [+/-] | |
| Burn rate | $[X]M | $[X]M | [+/-] | |
| Runway | [X]mo | [X]mo | | |
| [Key metric 1] | [plan] | [actual] | | |
| [Key metric 2] | [plan] | [actual] | | |
3. GREEN FLAGS: What's going better than expected?
4. YELLOW FLAGS: What needs watching but isn't critical yet?
5. RED FLAGS: What could kill this company or require urgent intervention?
6. BOARD AGENDA PRIORITIES: Top 3 things I should drive discussion on at the next board meeting.
7. FOLLOW-ON SIGNAL: Is this company a candidate for follow-on investment? [Yes / No / Maybe — with rationale]
8. MY ACTION ITEMS: What do I personally need to do for this company this month?
Portfolio-level KPI roll-up
Generate a portfolio health dashboard from these company updates.
FUND: [fund name]
REPORTING PERIOD: [Q? 202?]
PORTFOLIO SIZE: [X] companies
For each company, I'll provide a brief update. Synthesize across the portfolio:
[Company 1 — name, stage, sector]:
- ARR/Revenue: $[X]M, [+/-X]% vs. plan
- Gross margin: [X]%
- Burn: $[X]M/month, [X] months runway
- Key flag: [one sentence — good or bad]
[Company 2]: [same format]
[Company N]: [same format]
Generate:
## Portfolio Health Dashboard — [Period]
### Summary Stats
- Portfolio companies: [N]
- Total revenue/ARR across portfolio: $[X]M
- Average runway: [X] months
- Companies ahead of plan: [N] / [N total]
- Companies behind plan (>10%): [N]
- Companies with <6 months runway: [N] — [list them]
### Traffic Light Summary
| Company | Status | Primary Flag |
|---|---|---|
| [A] | Green | [brief note] |
| [B] | Yellow | [brief note] |
| [C] | Red | [brief note] |
### Follow-On Candidates
[Companies showing breakout metrics worth investing more capital]
### Intervention Needed
[Companies that need active help — board changes, bridge, pivot, M&A]
### LP Update Framing
[2-3 sentences framing portfolio performance for LP communication — accurate, not spin]
Board meeting prep
Prepare me for a board meeting with [company name].
COMPANY: [name]
MEETING DATE: [date]
BOARD COMPOSITION: [list of members — other investors, independents, founders]
MY ROLE: [lead investor / board observer / co-investor]
RECENT HISTORY:
- Last board meeting highlights: [key topics, decisions made, action items]
- Progress on prior action items: [what was committed vs. delivered]
CURRENT STATE (from most recent board package):
[Paste key financials and update]
KNOWN TENSIONS:
[Any board dynamics, founder conflicts, prior disagreements — be honest]
Prepare:
1. PRE-READ SYNTHESIS: 5 bullets on the most important things to know walking in
2. MY AGENDA: The 3 topics I want to drive (not just respond to)
3. HARD QUESTIONS to ask management — direct, not political
4. POTENTIAL ASKS FROM THE TEAM: What will they ask me for?
5. RED LINES: What decisions should I push back on?
6. POST-MEETING ACTION ITEMS I should expect to own
Follow-on investment trigger analysis
Analyze follow-on investment potential for [company name].
ORIGINAL INVESTMENT:
- Entry: $[X]M at $[X]M valuation ([date])
- Current stake: [X]%
- Current fair value: $[X]M (estimated)
CURRENT METRICS:
- ARR: $[X]M ([X]% YoY growth)
- Gross margin: [X]%
- NRR: [X]%
- Burn: $[X]M/month, [X] months runway
- Last round: [date and terms]
MARKET CONTEXT:
- Comps currently trading at: [X]x ARR
- Round environment: [active / tight / Series A drought / etc.]
FOLLOW-ON TRIGGERS (check applicable):
[ ] ARR milestone crossed (e.g., $1M → $5M → $10M ARR)
[ ] Product-market fit signals confirmed (NRR >120%, low churn)
[ ] Key hire made that unblocks next phase (enterprise sales leader, CFO)
[ ] New strategic customer signed that validates ICP
[ ] Competitive window closing — need to fund faster
[ ] Bridge round to extend runway to next milestone
DILUTION CALCULATION:
- If I invest $[X]M in a $[X]M round at $[X]M pre-money:
- New stake: [X]%
- Average cost basis: $[X]M per 1%
- MOIC to target at exit at $[X]M: [X]x
Generate a follow-on recommendation: [invest / pass / wait for specific trigger] with rationale.
LP quarterly report — portfolio section
Write the portfolio section of our quarterly LP report.
FUND: [fund name and vintage]
REPORTING PERIOD: [Q? 202?]
AUDIENCE: [institutional LPs / family offices / HNW individuals]
PORTFOLIO COMPANIES (provide for each):
[Company 1]:
- What they do: [1 sentence]
- Stage: [seed / Series A / growth]
- Our ownership: [X]%
- Key achievement this quarter: [milestone, customer, metric]
- Status: [on track / ahead / needs attention]
[Company N]: [same format]
FUND-LEVEL METRICS:
- Deployed capital: $[X]M / $[X]M total fund
- Fair value of portfolio: $[X]M ([X]x MOIC unrealized)
- Any realized exits this quarter: [yes / no — details]
- New investments this quarter: [X companies / $[X]M deployed]
Write the portfolio section:
1. Opening paragraph: how the portfolio performed vs. the fund thesis
2. Company-by-company highlights (2-3 sentences each — milestone focus, no spin)
3. Companies to watch (positive signals)
4. Portfolio support we've provided (intros, hires, customer referrals)
5. Fund deployment status
Tone: Professional, honest, detailed. LPs who read many of these will spot generic language. Lead with facts and let the facts do the work.
Red flag escalation template
A portfolio company is showing concerning signals. Help me assess severity and plan a response.
COMPANY: [name]
OUR STAKE: [X]%
CURRENT SITUATION:
[Describe what you're seeing — missed numbers, management issues, market changes, etc.]
RED FLAG CHECKLIST:
[ ] Revenue declining for [X] consecutive months
[ ] Burn increasing without corresponding revenue growth
[ ] Runway under 6 months with no fundraise in progress
[ ] Key executive departure (CTO, VP Sales, CFO)
[ ] Customer churn spike (gross churn > [X]%)
[ ] Lost a major customer (>15% of revenue)
[ ] Founder conflict or co-founder departure
[ ] Regulatory issue or legal dispute
[ ] Market conditions change that invalidates core thesis
SEVERITY ASSESSMENT:
For each flagged item: [Severity: Critical / High / Medium] | [Time to resolve: weeks / months]
RESPONSE OPTIONS:
1. ACTIVE SUPPORT: What can I do as a board member to help? (intros, hires, customer referrals)
2. BRIDGE FINANCING: Is bridge capital warranted? At what valuation and terms?
3. MANAGEMENT CHANGE: Is this a management problem or a market problem?
4. M&A / SOFT LANDING: Is there an acqui-hire or strategic buyer to explore?
5. WRITE-DOWN: What would trigger a write-down of our position?
Generate an action plan with 30/60/90 day milestones.
Example
User: I have three portfolio companies reporting for Q1. Company A (SaaS, Series A) hit 108% of ARR plan at $4.2M ARR, NRR 118%, burn on track. Company B (marketplace, seed) missed GMV plan by 22%, burned 2x expected, 7 months runway. Company C (dev tools, seed) on plan, landed first enterprise customer, but CTO just quit.
Expected output: Portfolio health dashboard with Company A as Green (ahead of plan, potential follow-on trigger), Company B as Red (missed plan + burn issue = intervention needed — specific actions: bridge analysis, burn reduction options, founder conversation), Company C as Yellow (enterprise win is positive but CTO departure is a 60-day clock on product continuity — board agenda: interim CTO plan, founder retention). LP framing for the quarter: balanced, leads with Company A win, addresses B and C with specific actions taken.