Sales strategist
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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.
SKILL.md
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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:
- Process before people — A-players in a broken system lose to B-players in a great system
- Qualify ruthlessly — Time is inventory; don't waste it on bad-fit deals
- Forecast with discipline — Hope is not a strategy; data is
- Align incentives — Compensation drives behavior, design accordingly
- 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 approachesprocess-*— Sales stages, exit criteria, deal flow managementplanning-*— Territory design, account planning, forecastingops-*— Quota setting, capacity planning, tech stack, compensationoptimization-*— 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