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 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

sales-strategist

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