sales-strategist

What this skill does

# Sales Strategist

Strategic sales operations expertise for B2B SaaS companies — from process design and methodology selection to compensation planning and pipeline optimization.

## Philosophy

Great sales organizations are built on **process, not heroics**. The best quota-crushing reps eventually leave, but excellent sales systems compound.

The best B2B sales strategies:
1. **Process before people** — A-players in a broken system lose to B-players in a great system
2. **Qualify ruthlessly** — Time is inventory; don't waste it on bad-fit deals
3. **Forecast with discipline** — Hope is not a strategy; data is
4. **Align incentives** — Compensation drives behavior, design accordingly
5. **Iterate constantly** — Sales is a science; run experiments, measure results

## How This Skill Works

When invoked, apply the guidelines in `rules/` organized by:

- `methodology-*` — Sales frameworks, qualification criteria, selling approaches
- `process-*` — Sales stages, exit criteria, deal flow management
- `planning-*` — Territory design, account planning, forecasting
- `ops-*` — Quota setting, capacity planning, tech stack, compensation
- `optimization-*` — Win rate analysis, deal velocity, pipeline health

## Core Frameworks

### Sales Qualification Frameworks

| Framework | Focus | Best For | Key Questions |
|-----------|-------|----------|---------------|
| **MEDDIC** | Deal qualification | Enterprise, complex sales | Metrics, Economic Buyer, Decision criteria, Decision process, Identify pain, Champion |
| **BANT** | Lead qualification | Transactional, high volume | Budget, Authority, Need, Timeline |
| **SPICED** | Discovery | Consultative sales | Situation, Pain, Impact, Critical Event, Decision |
| **SCOTSMAN** | Opportunity scoring | Mid-market | Solution, Competition, Originality, Timescales, Size, Money, Authority, Need |
| **CHAMP** | Modern qualification | SaaS, product-led | Challenges, Authority, Money, Prioritization |

### The Sales Pipeline Hierarchy

```
                    ┌─────────────────┐
                    │    Closed Won   │  ← Revenue
                    ├─────────────────┤
                    │   Negotiation   │  ← Contract stage
                    ├─────────────────┤
                    │    Proposal     │  ← Pricing/SOW
                    ├─────────────────┤
                    │   Evaluation    │  ← POC/Trial
                    ├─────────────────┤
                    │   Discovery     │  ← Qualification
                    ├─────────────────┤
                    │  Meeting Set    │  ← First meeting
                    └─────────────────┘
```

### Sales Motion by ACV

| ACV Range | Motion | Team Structure | Sales Cycle |
|-----------|--------|----------------|-------------|
| **<$5K** | Self-serve/PLG | No AEs, maybe Success | Days-weeks |
| **$5K-$25K** | Transactional | SDR → AE (1:4 ratio) | 2-6 weeks |
| **$25K-$100K** | Mid-market | SDR → AE → CSM | 1-3 months |
| **$100K-$500K** | Enterprise | SDR → AE → SE → CSM | 3-9 months |
| **>$500K** | Strategic | Named accounts, exec sponsors | 6-18 months |

### Pipeline Coverage Model

```
┌─────────────────────────────────────────────────────────────┐
│                    PIPELINE MATH                            │
├─────────────────────────────────────────────────────────────┤
│  Target Revenue: $1M                                        │
│  Win Rate: 25%                                              │
│  Required Pipeline: $4M (4x coverage)                       │
│                                                             │
│  Average Deal Size: $50K                                    │
│  Deals Needed: 80 opportunities                             │
│                                                             │
│  Meeting → Opportunity Rate: 40%                            │
│  Meetings Needed: 200                                       │
│                                                             │
│  Response → Meeting Rate: 20%                               │
│  Outreach Needed: 1,000 responses                           │
└─────────────────────────────────────────────────────────────┘
```

### Comp Plan Architecture

```
┌─────────────────────────────────────────────────────────────┐
│                 COMPENSATION STRUCTURE                       │
├─────────────────────────────────────────────────────────────┤
│  Role          │ Base:Variable │ OTE Range    │ Quota Multiple│
│  ─────────────────────────────────────────────────────────  │
│  SDR           │ 70:30        │ $70-100K     │ N/A (activity) │
│  AE (SMB)      │ 50:50        │ $100-150K    │ 4-5x OTE      │
│  AE (MM)       │ 50:50        │ $150-250K    │ 4-5x OTE      │
│  AE (Ent)      │ 60:40        │ $250-400K    │ 3-4x OTE      │
│  Sales Mgr     │ 60:40        │ $200-350K    │ Team rollup   │
└─────────────────────────────────────────────────────────────┘
```

## Sales Technology Stack

| Layer | Tools | Purpose |
|-------|-------|---------|
| **CRM** | Salesforce, HubSpot, Pipedrive | System of record |
| **Engagement** | Outreach, Salesloft, Apollo | Sequences, cadences |
| **Intelligence** | Gong, Chorus, Clari | Call recording, forecasting |
| **Enrichment** | ZoomInfo, Clearbit, Apollo | Contact/account data |
| **Scheduling** | Calendly, Chili Piper | Meeting booking |
| **CPQ** | DealHub, PandaDoc, Proposify | Quotes, contracts |
| **Analytics** | Clari, InsightSquared, Atrium | Pipeline analytics |

## Anti-Patterns

- **Happy ears** — Believing what prospects say without validation
- **Demo-first selling** — Showing product before understanding pain
- **Single-threaded deals** — Only one contact at an account
- **Sandbagged forecasts** — Reps hiding deals to sandbag
- **Commission clawback abuse** — Punishing reps for customer churn they can't control
- **Territory chaos** — Unclear or overlapping territories creating conflict
- **Discounting addiction** — Training buyers to always ask for discounts
- **Vanity pipeline** — Inflated stages, zombie deals, false confidence