cro-advisor

What this skill does

# CRO Advisor

Revenue frameworks for building predictable, scalable revenue engines -- from first revenue to $100M ARR and beyond. Every recommendation is grounded in pipeline math, not hope.

## Keywords

CRO, chief revenue officer, revenue strategy, ARR, MRR, sales model, pipeline, revenue forecasting, pricing strategy, net revenue retention, NRR, gross revenue retention, GRR, expansion revenue, upsell, cross-sell, churn, customer success, sales capacity, quota, ramp, territory design, MEDDPICC, PLG, product-led growth, sales-led growth, enterprise sales, SMB, self-serve, value-based pricing, usage-based pricing, ICP, ideal customer profile, revenue board reporting, sales cycle, CAC payback, magic number, win rate, pipeline coverage, deal velocity

---

## Revenue Health Diagnostic

Before applying any framework, diagnose the current state.

### Revenue Health Decision Tree

```
START: "How healthy is our revenue engine?"
  |
  v
[Check NRR]
  |
  +-- NRR < 90% --> CRISIS. Existing customers are shrinking.
  |                  Stop scaling sales. Fix retention first.
  |
  +-- NRR 90-100% --> WARNING. Churn eating expansion.
  |                    Diagnose: product gap, CS gap, or ICP problem?
  |
  +-- NRR 100-110% --> HEALTHY. Base is stable. Focus on new logo + expansion.
  |
  +-- NRR > 110% --> STRONG. Expansion engine is working.
                      Check: is it sustainable or driven by price increases?
```

### Revenue Waterfall

```
Opening ARR
  + New Logo ARR       (new customers closed this period)
  + Expansion ARR      (upsell, cross-sell, seat adds)
  - Contraction ARR    (downgrades, reduced usage)
  - Churned ARR        (lost customers)
= Closing ARR

NRR = (Opening + Expansion - Contraction - Churn) / Opening x 100
GRR = (Opening - Contraction - Churn) / Opening x 100
```

---

## Revenue Metrics

### Board-Level Metrics (Monthly/Quarterly)

| Metric | Formula | Target | Red Flag |
|--------|---------|--------|----------|
| ARR Growth YoY | (Current ARR / Prior Year ARR) - 1 | 2x+ early stage, 50%+ growth | Decelerating 2+ quarters |
| NRR | See waterfall above | > 110% | < 100% |
| GRR | See waterfall above | > 85% | < 80% |
| Pipeline Coverage | Open pipeline / Quota | > 3x | < 2x entering quarter |
| Magic Number | Net New ARR x 4 / Prior Q S&M Spend | > 0.75 | < 0.5 |
| CAC Payback | S&M Spend / New ARR x (1/GM%) | < 18 months | > 24 months |
| Quota Attainment | % of reps hitting quota | 60-70% | < 50% |
| Win Rate | Closed-won / (Closed-won + Closed-lost) | > 25% | < 15% |
| Average Sales Cycle | Days from opportunity to close | Stable or decreasing | Increasing 2+ quarters |

### NRR Benchmarks

| NRR Range | Signal | Strategic Implication |
|-----------|--------|----------------------|
| > 130% | World-class (Snowflake, Twilio) | Can grow even with zero new logos |
| 110-130% | Excellent | Strong expansion motion, invest in new logo |
| 100-110% | Healthy | Expansion offsets churn, monitor trends |
| 90-100% | Concerning | Churn exceeds expansion, fix before scaling |
| < 90% | Critical | Leaky bucket, all new revenue evaporates |

---

## Sales Model Selection

### Model Comparison Matrix

| Model | ACV Range | Sales Cycle | Team | Best For |
|-------|-----------|-------------|------|----------|
| Self-serve / PLG | $0-$10K | Minutes-days | No sales team | High volume, simple product |
| SMB inside sales | $5K-$50K | 2-6 weeks | SDR + AE | Mid-volume, moderate complexity |
| Mid-market | $25K-$150K | 4-12 weeks | SDR + AE + SE | Complex product, multiple stakeholders |
| Enterprise | $100K-$1M+ | 3-12 months | AE + SE + CSM + exec sponsor | Large organizations, high touch |
| Channel/Partner | Varies | Varies | Partner manager + enablement | Market coverage, geographic reach |

### Model Selection Decision Tree

```
START: "Which sales model?"
  |
  v
[What's the average deal size?]
  |
  +-- < $5K ACV --> Self-serve / PLG
  |                  (add sales assist at $2-5K for upsell)
  |
  +-- $5K-$50K --> Inside sales (SMB)
  |                (SDRs + AEs, high velocity)
  |
  +-- $50K-$200K --> Mid-market
  |                  (SDR + AE + SE, consultative)
  |
  +-- > $200K --> Enterprise
                  (Named accounts, multi-threaded, executive selling)

HYBRID: Most companies evolve to serve 2-3 segments.
Route by ACV and buying complexity.
```

---

## Pipeline Management

### Pipeline Stage Definitions

| Stage | Definition | Exit Criteria | Typical Conversion |
|-------|-----------|---------------|-------------------|
| 0: Lead | Inbound inquiry or outbound target | Qualified as ICP fit | 20-30% to Stage 1 |
| 1: Discovery | First meeting completed | Pain confirmed, authority identified | 50-60% to Stage 2 |
| 2: Evaluation | Active evaluation, demo/POC | Champion identified, timeline set | 40-50% to Stage 3 |
| 3: Proposal | Proposal/pricing delivered | Budget confirmed, decision criteria clear | 50-60% to Stage 4 |
| 4: Negotiation | Terms being negotiated | Legal/procurement engaged | 70-80% to Close |
| 5: Closed-Won | Contract signed | Revenue recognized | -- |
| X: Closed-Lost | Deal lost | Loss reason documented | -- |

### Pipeline Coverage Model

| Quarter Position | Required Pipeline Coverage | Action If Below |
|-----------------|--------------------------|-----------------|
| Q-1 (planning) | 4x quota | Increase top-of-funnel activity |
| Q start | 3x quota | Accelerate existing deals, add pipeline |
| Mid-quarter | 2x quota | Deal acceleration, executive engagement |
| Q-end | 1.5x quota | Forecast adjustment, pull-in deals |

### Deal Qualification: MEDDPICC

| Element | Question | Red Flag |
|---------|----------|----------|
| **M**etrics | What business outcome does the buyer measure? | No quantified value proposition |
| **E**conomic Buyer | Who signs the check? Have we met them? | Never met the decision-maker |
| **D**ecision Criteria | What criteria will they use to decide? | "We'll know it when we see it" |
| **D**ecision Process | What are the steps to get to a yes? | No defined process or timeline |
| **P**aper Process | What legal/procurement steps are required? | Unknown procurement process |
| **I**dentify Pain | What problem are they solving? Is it urgent? | Pain is theoretical, not acute |
| **C**hampion | Who internally advocates for us? | No internal champion identified |
| **C**ompetition | Who else are they evaluating? | "They said no competition" (always wrong) |

---

## Pricing Strategy

### Pricing Model Selection

| Model | Best When | Watch Out For |
|-------|-----------|--------------|
| Per-seat | Value scales with users | Seat consolidation games |
| Usage-based | Value directly tied to consumption | Revenue unpredictability |
| Tiered | Clear feature differentiation between segments | Tier boundaries feel arbitrary |
| Flat-rate | Simple product, uniform usage | Leaves money on table for heavy users |
| Value-based | Clear ROI measurement possible | Requires trust and proof |
| Hybrid | Complex product with multiple value dimensions | Complexity in quoting |

### Pricing Decision Framework

```
START: "How should we price?"
  |
  v
[What is the primary value driver for the customer?]
  |
  +-- Number of users --> Per-seat pricing
  |
  +-- Volume of usage --> Usage-based pricing
  |
  +-- Feature needs differ by segment --> Tiered pricing
  |
  +-- Clear ROI (saves $X) --> Value-based (price at 10-20% of value)
  |
  +-- Multiple value drivers --> Hybrid (base + usage/seats)
```

### Pricing Health Indicators

| Signal | Healthy | Unhealthy |
|--------|---------|-----------|
| Price objection rate | < 20% of proposals | > 40% = value communication broken |
| Discount rate (avg) | < 15% off list | > 25% = pricing not anchored to value |
| Time since last increase | < 12 months | > 24 months = inflation eating margin |
| Price increase churn | < 2% incremental churn | > 5% = increase was too aggressive |
| Win rate after increase | Stable or improved | Dropped > 10 points =