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sales-strategist skill

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This skill provides strategic sales operations guidance for B2B SaaS, helping design processes, qualification frameworks, territory planning, forecasting, and

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SKILL.md

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---
name: sales-strategist
description: Expert sales strategy and operations guidance for B2B SaaS companies. Use when designing sales processes, implementing qualification frameworks (MEDDIC, BANT, SPICED), territory planning, forecasting, quota setting, compensation design, or optimizing pipeline velocity. Covers sales methodology, org structure, tech stack selection, win rate analysis, and deal acceleration strategies.
---

# 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

Overview

This skill provides expert sales strategy and operations guidance tailored to B2B SaaS companies. It helps design repeatable sales processes, choose qualification frameworks, set quotas and compensation, and optimize pipeline velocity to increase predictable revenue. The goal is durable systems that scale beyond individual performers.

How this skill works

When invoked, the skill applies practical playbooks across methodology, process, planning, ops, and optimization. It recommends qualification frameworks (MEDDIC, BANT, SPICED), defines stage exit criteria and deal flows, models territory and capacity, and prescribes comp plans and tech stack choices. Outputs are actionable: stage definitions, scorecards, coverage math, quota targets, and experiment ideas for improving win rates and velocity.

When to use it

Designing or standardizing a sales process for a new or scaling SaaS product
Choosing or implementing qualification frameworks for reps and SDRs
Setting quotas, territory assignments, capacity planning, or comp plans
Forecasting, pipeline coverage modeling, and deal velocity optimization
Evaluating or selecting sales technology (CRM, engagement, intelligence)
Diagnosing low win rates, long sales cycles, or unreliable forecasts

Best practices

Prioritize process before hiring — document stages, exit criteria, and scorecards
Qualify ruthlessly using a chosen framework and insist on evidence for close-related criteria
Base forecasts on disciplined stage-level conversion rates and pipeline coverage math
Align compensation to desired behaviors; test a single variable at a time
Instrument the funnel: track stage conversion, time-in-stage, multi-threading, and activity metrics
Run A/B experiments on cadence, messaging, and qualification to incrementally improve metrics

Example use cases

Build a territory plan and capacity model to hire the next 12 months of AEs and SDRs
Switch from demo-first to MEDDIC-driven qualification for enterprise deals to improve win rates
Design an AE compensation plan with 50:50 or 60:40 base:variable and quota multiple guidance
Calculate required pipeline coverage to hit a quarterly revenue target given current win rates
Recommend a tech stack (CRM, engagement, call intelligence, CPQ) aligned to motion and ACV
Diagnose a high-volume pipeline with many zombie deals and prescribe cleanup rules and gating

FAQ

Which qualification framework should I choose?

Match the framework to deal complexity: use BANT for high-volume transactional deals, SPICED for consultative discovery, and MEDDIC for complex enterprise sales.

How do I set quota coverage targets?

Start from target revenue and historical win rate: required pipeline = target / win rate. Adjust for sales cycle length and ramp assumptions.

What are the quickest levers to improve forecast accuracy?

Enforce exit criteria, require evidence for stage entry, reduce single-threaded deals, and track time-in-stage plus historical conversion rates.