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