@monoes/monomindcli 2.15.3 → 2.15.5

package/org-skills/cfo-advisor/SKILL.md

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+---
+name: cfo-advisor
+description: "Financial leadership for startups and scaling companies. Financial modeling, unit economics, fundraising strategy, cash management, and board financial packages. Use when building financial models, analyzing unit economics, planning fundraising, managing cash runway, preparing board materials, or when user mentions CFO, burn rate, runway, fundraising, unit economics, LTV, CAC, term sheets, or..."
+tags: ["leadership","finance"]
+tools: []
+license: MIT
+source: https://github.com/alirezarezvani/claude-skills
+source_path: "c-level-advisor/skills/cfo-advisor"
+source_commit: 19392f7a08264ed00486a251f5b2098321771f94
+---
+# CFO Advisor
+
+Strategic financial frameworks for startup CFOs and finance leaders. Numbers-driven, decisions-focused.
+
+This is **not** a financial analyst skill. This is strategic: models that drive decisions, fundraises that don't kill the company, board packages that earn trust.
+
+## Keywords
+CFO, chief financial officer, burn rate, runway, unit economics, LTV, CAC, fundraising, Series A, Series B, term sheet, cap table, dilution, financial model, cash flow, board financials, FP&A, SaaS metrics, ARR, MRR, net dollar retention, gross margin, scenario planning, cash management, treasury, working capital, burn multiple, rule of 40
+
+## Quick Start
+
+```bash
+# Burn rate & runway scenarios (base/bull/bear)
+python scripts/burn_rate_calculator.py
+
+# Per-cohort LTV, per-channel CAC, payback periods
+python scripts/unit_economics_analyzer.py
+
+# Dilution modeling, cap table projections, round scenarios
+python scripts/fundraising_model.py
+```
+
+## Key Questions (ask these first)
+
+- **What's your burn multiple?** (Net burn ÷ Net new ARR. > 2x is a problem.)
+- **If fundraising takes 6 months instead of 3, do you survive?** (If not, you're already behind.)
+- **Show me unit economics per cohort, not blended.** (Blended hides deterioration.)
+- **What's your NDR?** (> 100% means you grow without signing a single new customer.)
+- **What are your decision triggers?** (At what runway do you start cutting? Define now, not in a crisis.)
+
+## Core Responsibilities
+
+| Area | What It Covers | Reference |
+|------|---------------|-----------|
+| **Financial Modeling** | Bottoms-up P&L, three-statement model, headcount cost model | `references/financial_planning.md` |
+| **Unit Economics** | LTV by cohort, CAC by channel, payback periods | `references/financial_planning.md` |
+| **Burn & Runway** | Gross/net burn, burn multiple, scenario planning, decision triggers | `references/cash_management.md` |
+| **Fundraising** | Timing, valuation, dilution, term sheets, data room | `references/fundraising_playbook.md` |
+| **Board Financials** | What boards want, board pack structure, BvA | `references/financial_planning.md` |
+| **Cash Management** | Treasury, AR/AP optimization, runway extension tactics | `references/cash_management.md` |
+| **Budget Process** | Driver-based budgeting, allocation frameworks | `references/financial_planning.md` |
+
+## CFO Metrics Dashboard
+
+| Category | Metric | Target | Frequency |
+|----------|--------|--------|-----------|
+| **Efficiency** | Burn Multiple | < 1.5x | Monthly |
+| **Efficiency** | Rule of 40 | > 40 | Quarterly |
+| **Efficiency** | Revenue per FTE | Track trend | Quarterly |
+| **Revenue** | ARR growth (YoY) | > 2x at Series A/B | Monthly |
+| **Revenue** | Net Dollar Retention | > 110% | Monthly |
+| **Revenue** | Gross Margin | > 65% | Monthly |
+| **Economics** | LTV:CAC | > 3x | Monthly |
+| **Economics** | CAC Payback | < 18 mo | Monthly |
+| **Cash** | Runway | > 12 mo | Monthly |
+| **Cash** | AR > 60 days | < 5% of AR | Monthly |
+
+## Red Flags
+
+- Burn multiple rising while growth slows (worst combination)
+- Gross margin declining month-over-month
+- Net Dollar Retention < 100% (revenue shrinks even without new churn)
+- Cash runway < 9 months with no fundraise in process
+- LTV:CAC declining across successive cohorts
+- Any single customer > 20% of ARR (concentration risk)
+- CFO doesn't know cash balance on any given day
+
+## Integration with Other C-Suite Roles
+
+| When... | CFO works with... | To... |
+|---------|-------------------|-------|
+| Headcount plan changes | CEO + COO | Model full loaded cost impact of every new hire |
+| Revenue targets shift | CRO | Recalibrate budget, CAC targets, quota capacity |
+| Roadmap scope changes | CTO + CPO | Assess R&D spend vs. revenue impact |
+| Fundraising | CEO | Lead financial narrative, model, data room |
+| Board prep | CEO | Own financial section of board pack |
+| Compensation design | CHRO | Model total comp cost, equity grants, burn impact |
+| Pricing changes | CPO + CRO | Model ARR impact, LTV change, margin impact |
+
+## Resources
+
+- `references/financial_planning.md` — Modeling, SaaS metrics, FP&A, BvA frameworks
+- `references/fundraising_playbook.md` — Valuation, term sheets, cap table, data room
+- `references/cash_management.md` — Treasury, AR/AP, runway extension, cut vs invest decisions
+- `scripts/burn_rate_calculator.py` — Runway modeling with hiring plan + scenarios
+- `scripts/unit_economics_analyzer.py` — Per-cohort LTV, per-channel CAC
+- `scripts/fundraising_model.py` — Dilution, cap table, multi-round projections
+
+
+## Proactive Triggers
+
+Surface these without being asked when you detect them in company context:
+- Runway < 18 months with no fundraising plan → raise the alarm early
+- Burn multiple > 2x for 2+ consecutive months → spending outpacing growth
+- Unit economics deteriorating by cohort → acquisition strategy needs review
+- No scenario planning done → build base/bull/bear before you need them
+- Budget vs actual variance > 20% in any category → investigate immediately
+
+## Output Artifacts
+
+| Request | You Produce |
+|---------|-------------|
+| "How much runway do we have?" | Runway model with base/bull/bear scenarios |
+| "Prep for fundraising" | Fundraising readiness package (metrics, deck financials, cap table) |
+| "Analyze our unit economics" | Per-cohort LTV, per-channel CAC, payback, with trends |
+| "Build the budget" | Zero-based or incremental budget with allocation framework |
+| "Board financial section" | P&L summary, cash position, burn, forecast, asks |
+
+## Reasoning Technique: Chain of Thought
+
+Work through financial logic step by step. Show all math. Be conservative in projections — model the downside first, then the upside. Never round in your favor.
+
+## Communication
+
+All output passes the Internal Quality Loop before reaching the founder (see `../agent-protocol/SKILL.md`).
+- Self-verify: source attribution, assumption audit, confidence scoring
+- Peer-verify: cross-functional claims validated by the owning role
+- Critic pre-screen: high-stakes decisions reviewed by Executive Mentor
+- Output format: Bottom Line → What (with confidence) → Why → How to Act → Your Decision
+- Results only. Every finding tagged: 🟢 verified, 🟡 medium, 🔴 assumed.
+
+## Context Integration
+
+- **Always** read `company-context.md` before responding (if it exists)
+- **During board meetings:** Use only your own analysis in Phase 2 (no cross-pollination)
+- **Invocation:** You can request input from other roles: `[INVOKE:role|question]`

package/org-skills/cfo-advisor/references/cash_management.md

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+# Cash Management Reference
+
+Cash is the oxygen of a startup. You can be unprofitable for years. You cannot be out of cash for a day.
+
+---
+
+## 1. Cash Flow Management
+
+### The Cash Equation
+
+```
+Ending Cash = Beginning Cash
+            + Cash collected from customers
+            - Cash paid to employees
+            - Cash paid to vendors
+            - Cash paid for infrastructure
+            - Debt service
+            +/- Financing activities
+
+Note: This is NOT the P&L. Revenue recognition ≠ cash collected.
+```
+
+### Where Cash Hides (and Leaks)
+
+**Cash sources you might be under-using:**
+- Deferred revenue (annual billing locks in cash 12 months early)
+- Customer deposits on enterprise contracts
+- Vendor payment terms (Net 60 instead of Net 30 = free float)
+- AWS/GCP startup credits (often $25K–$100K available, widely unused)
+- Revenue-based financing on predictable MRR
+- Venture debt (non-dilutive, available post-Series A)
+
+**Cash drains that sneak up on you:**
+- Annual software licenses paid in Q1 (budget for the lump sum)
+- Event sponsorships (often 6-12 months in advance)
+- Recruiting fees (15-25% of first-year salary, due on hire)
+- Legal fees (data room prep, fundraise close = $50K–$200K surprise)
+- Late-paying enterprise customers (Net 60 in contract, pays Net 90 in practice)
+
+### Cash Flow vs P&L: The Gap
+
+**Scenario: $1M enterprise deal signed December 31**
+
+```
+P&L impact (accrual):
+  December revenue: $83K (1/12 of annual)
+
+Cash impact:
+  If billed annually upfront:  +$1,000K in December (GREAT)
+  If billed quarterly:         +$250K in December (good)
+  If billed monthly:           +$83K in December (fine)
+  If Net 60 terms:             +$0 in December, +$83K in February (cash drag)
+```
+
+**The CFO's job:** Maximize the timing difference between cash in and cash out.
+- Collect from customers as early as possible (annual upfront, early payment discounts)
+- Pay vendors as late as possible (maximize payment terms)
+- Never confuse deferred revenue (a liability) with actual cash (it is cash — just count it right)
+
+---
+
+## 2. Treasury and Banking Strategy
+
+### Account Structure
+
+```
+Operating Account (primary bank):
+  Balance: 3-6 months of operating expenses
+  Purpose: Payroll, vendor payments, day-to-day ops
+  Product: Business checking or high-yield business savings
+  Bank: Chase, SVB successor (First Citizens), Mercury, Brex
+
+Reserve Account (secondary or same bank):
+  Balance: Everything above operating float
+  Purpose: Reserve; move to operating as needed
+  Product: Money market fund or T-Bill ladder
+  Target yield (2024-2025): 4.5%–5.2%
+  Products: Vanguard VMFXX, Fidelity SPAXX, or direct T-Bills via TreasuryDirect
+
+Emergency Account (separate bank):
+  Balance: 1-2 months expenses
+  Purpose: If primary bank has issues (SVB taught this lesson)
+  Product: Business savings
+```
+
+**FDIC coverage:** $250K per depositor per institution. For balances above $250K at a single bank, either:
+- Use CDARS/ICS (bank sweeps into multiple FDIC-insured accounts automatically)
+- Spread across multiple banks
+- Move excess to T-Bills (backed by US government, not FDIC, but safer)
+
+**After SVB (March 2023):** Every CFO should have at least 2 banking relationships. If one bank fails or freezes, you can make payroll.
+
+### Yield on Cash
+
+At $3M cash, the difference between 0% (checking) and 5% (T-Bills) is $150K/year.
+That's a month of runway for a $150K/month burn company. **Get yield on reserves.**
+
+```
+Monthly yield on $3M at 5%: ~$12,500
+Annual: ~$150,000
+This is not optional. Set it up once and automate.
+```
+
+---
+
+## 3. AR/AP Optimization
+
+### Accounts Receivable: Get Paid Faster
+
+**Billing model impact on cash:**
+```
+                Annual Upfront  Quarterly    Monthly    Net 30 Monthly
+Cash Day 1:      100% of ACV     25% of ACV    8.3%       0%
+Cash Month 2:    0% (done)       0%            8.3%       8.3%
+12-month total:  100%            100%          100%       100%
+
+For $100K ACV customer, Year 1 cash:
+  Annual upfront:  $100K immediately
+  Monthly Net 30:  $8.3K × 11 months = $91.7K (1 month lag)
+  Cash benefit:    $100K vs $91.7K = $8.3K benefit + no collection risk
+```
+
+**Push for annual billing. Make it easy with a discount:**
+```
+"Pay annually and get 2 months free (16% discount)"
+Most SMB customers will take this.
+Enterprise: use MSA structure with annual invoicing, not month-to-month.
+```
+
+**AR Aging Policy:**
+```
+> 0-30 days: Current. No action.
+> 30-60 days: Friendly reminder from AR team.
+> 60-90 days: Escalate to Customer Success.
+> 90 days:    CFO or CEO-level outreach. Consider collections.
+> 120 days:   Reserve for bad debt. Legal/collections.
+
+Reserve policy: 50% of 90-120 day AR, 100% of > 120 days
+```
+
+**What slows down collections:**
+- Wrong contact (billing contact vs. user) — get finance contact during onboarding
+- Enterprise PO required — know this upfront, not when invoice is due
+- Credit holds or budget freeze — your CSM should surface these early
+- Invoice errors — every wrong invoice extends payment by 30-60 days
+
+### Accounts Payable: Pay Slower
+
+**Standard terms by vendor type:**
+```
+SaaS tools:      Net 30 default. Push for Net 45 or Net 60 at scale.
+Cloud providers: Pay as you go. Apply for credits first.
+Professional services (agencies, lawyers): Net 30 minimum. Get Net 45 where possible.
+Rent/office:     Whatever the lease says. Negotiate quarterly payments if you can.
+Payroll:         Pay on time. Never delay payroll. Ever.
+```
+
+**Early payment discount trap:**
+```
+"2/10 Net 30" means: 2% discount if you pay in 10 days, else pay in 30.
+Annual cost of NOT taking this: 2% × (365/(30-10)) = ~36% APY
+ALWAYS take early payment discounts > 2%.
+Never take discounts < 1%.
+```
+
+**AP workflow:**
+1. All invoices → finance inbox (not individual employees)
+2. Approval required above threshold ($500 for startups)
+3. Pay at end of terms, not when invoice arrives
+4. Batch payments weekly (not daily) to reduce processing overhead
+
+---
+
+## 4. Runway Extension Tactics
+
+Use these when you need to extend runway without raising. Ranked by speed and impact.
+
+### Tier 1: Fast Cash (Days)
+
+**Annual billing campaign:**
+```
+Target: Existing monthly customers
+Offer: 2 months free (16% discount) or 1 month free (8% discount) for annual upfront
+Process: CSM-led email campaign to all monthly customers
+Impact: $X MRR × 12 × conversion rate = immediate cash injection
+Timeline: 2-4 weeks
+No dilution. No debt. High impact.
+```
+
+**Prepayment incentive for pipeline:**
+```
+For deals in late stage, offer annual upfront pricing with 10-15% discount.
+Close rate may increase. Cash timing dramatically improves.
+```
+
+### Tier 2: Cost Control (2-4 Weeks)
+
+**Hiring freeze:**
+```
+Every unfilled role = salary × 1.25 per month.
+For a 30-person company, 3 open roles at $150K average:
+  Monthly savings: 3 × $150K × 1.25 / 12 = $47K/month
+  Over 6 months: $280K
+Impact: Immediate. No blood.
+```
+
+**Software audit:**
+```
+Pull all credit card charges and ACH debits.
+Cancel any subscription not used in 30 days.
+Typical savings: $3K-$15K/month at Series A stage.
+Tools: Vendr, Spendesk, or just a spreadsheet of recurring charges.
+```
+
+**Cloud cost optimization:**
+```
+Right-size instances (dev/staging don't need prod-scale)
+Reserve instances (1-year reserved = 30-40% savings vs on-demand)
+Delete unused resources (load balancers, IPs, old snapshots)
+Typical savings: 20-35% of current cloud bill
+```
+
+### Tier 3: Vendor Renegotiation (2-6 Weeks)
+
+**Payment term extension:**
+```
+Ask key vendors for Net 60 instead of Net 30.
+$500K in AP × 30 days = $500K × (30/365) = ~$41K cash float improvement
+Won't always work, but vendors often say yes to good customers.
+```
+
+**Renewal timing:**
+```
+Push annual renewals to later in the year.
+Preserve cash for Q1 (typically heaviest sales hiring quarter).
+```
+
+**Vendor credits:**
+```
+AWS: AWS Activate (up to $100K for qualified startups)
+GCP: Google for Startups (up to $200K)
+Azure: Microsoft for Startups (up to $150K)
+Stripe: Revenue share programs
+Hubspot: Startup pricing (90% off)
+```
+
+### Tier 4: Financing (Weeks to Months)
+
+**Revenue-based financing:**
+```
+Providers: Clearco, Capchase, Pipe, Arc
+Structure: Advance 3-6 months of MRR. Repay with % of monthly revenue.
+Cost: Typically 6-12% annualized.
+Speed: 1-2 weeks to close.
+When to use: Bridge to next ARR milestone before raising equity.
+When NOT to use: When burn rate is structural (will consume the advance fast).
+```
+
+**Venture debt:**
+```
+Providers: SVB (now First Citizens), Western Technology Investment, Hercules, TriplePoint
+Structure: Term loan, typically 3-6x monthly gross burn
+Interest: Prime + 2-4% + warrants
+When available: Post-Series A, when revenue is predictable
+Typical timing: Add alongside an equity round (don't raise debt when you need equity)
+Impact: Extends runway 3-6 months without dilution
+When NOT to use: If you might trip financial covenants (minimum cash, revenue)
+```
+
+**Convertible bridge:**
+```
+Existing investors write bridge note: $500K-$2M at favorable terms.
+Structure: Converts at discount (10-20%) or cap into next equity round.
+When to use: You're 60-90 days from closing an equity round and need cash to get there.
+When NOT to use: As a long-term strategy. Bridge-to-bridge is a death spiral.
+```
+
+### Tier 5: Structural Cost Reduction (Weeks + Impact on Morale)
+
+**Salary deferrals (founders first):**
+```
+Founders take 20-30% salary reduction, accrued for future repayment.
+Signals commitment to team and investors.
+Only ask employees to follow if founders go first.
+Always pay market rate to key non-founder employees — you can't afford to lose them.
+```
+
+**Reduction in force (RIF):**
+```
+Threshold: If burn multiple > 3x and growth < 20% YoY, a RIF is likely necessary.
+Sizing: Model to achieve at least 12 months runway without fundraising.
+Rule: Don't do a RIF twice. Size it right the first time.
+  Two small RIFs destroy morale worse than one decisive one.
+Process: Legal counsel required. WARN Act (60-day notice) if > 100 employees.
+Focus cuts: G&A and underperforming sales roles first. Protect engineering and key revenue.
+```
+
+---
+
+## 5. When to Cut vs When to Invest
+
+### The Framework
+
+**Cut when:**
+- Burn multiple > 2x and growth is decelerating
+- Runway < 9 months with no fundraise imminent
+- LTV:CAC declining for 3+ consecutive months
+- Any spend category with no measurable return in 90 days
+- Headcount in functions not directly tied to near-term revenue or product-market fit
+
+**Invest when:**
+- Magic number > 1 (every dollar in S&M returns > $1 in gross profit)
+- LTV:CAC > 3x in a specific channel (pour money in)
+- Gross margin > 70% (unit economics are healthy; growth is the constraint)
+- Cohort data improving (retention getting better → LTV going up → invest in growth)
+- CAC payback < 12 months (you get your money back fast enough to keep reinvesting)
+
+### The False Economy Trap
+
+**Don't cut:** 
+- Top-of-funnel demand gen that generates qualified pipeline (if CAC payback is < 12 months, this is your best investment)
+- Engineering capacity on core product (technical debt compounds and slows you down permanently)
+- Key account managers on your largest customers (churn from top customers is catastrophic)
+
+**Cut these first:**
+- Conference sponsorships with no measurable pipeline
+- Tools and subscriptions with < 5 users or < 30% utilization
+- Agency spend that could be done in-house
+- Roadmap items that aren't tied to retention or expansion revenue
+- Any G&A spend that isn't legally required
+
+### Decision Triggers (Pre-Define These)
+
+Don't make these decisions in a crisis. Define the triggers now:
+
+```
+At 12 months runway:  Review all discretionary spend. Start fundraise process.
+At 9 months runway:   Implement hiring freeze. Fundraise is mandatory.
+At 6 months runway:   Cut non-essential spend 20%. If no fundraise term sheet, run RIF model.
+At 4 months runway:   Execute RIF. Explore all financing options. Notify board.
+At 3 months runway:   Emergency plan only. All options on table (bridge, strategic, wind down).
+```
+
+---
+
+## Key Formulas
+
+```python
+# Net burn
+net_burn = gross_burn - revenue_collected
+
+# Runway (months)
+runway_months = cash_balance / net_burn
+
+# Cash conversion cycle
+ccc = days_sales_outstanding + days_inventory_held - days_payable_outstanding
+# Lower CCC = better cash efficiency
+
+# Days Sales Outstanding (DSO)
+dso = (accounts_receivable / revenue) * 30  # monthly revenue
+
+# Days Payable Outstanding (DPO)
+dpo = (accounts_payable / cogs) * 30  # target: maximize this
+
+# Working capital
+working_capital = current_assets - current_liabilities
+
+# Quick ratio (liquidity)
+quick_ratio_liquidity = (cash + ar) / current_liabilities
+# Target: > 1.5 (you can pay short-term obligations without selling assets)
+
+# Free cash flow
+fcf = operating_cash_flow - capex
+```