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