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Sales

Skill samuelcastro/startup-skills/sales

Agent Skills for AI-native startup founders — a founder-playbook hub + 12 per-function skills. Adapted from Linas Beliūnas's One-Person Unicorn + Anthropic's Founder's Playbook.

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npx -y skills add samuelcastro/startup-skills --skill sales

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Guide founders through B2B sales from first deal to scalable sales engine. Use when a founder says "help me design my sales process", "how should I start selling this?", "write a cold email sequence", "create a demo script", "help me build a proposal", "how do I forecast my pipeline", "what CRM should I use", "SOW template", "sales playbook", or asks about outbound sales, closing deals, pipeline management, or sales team hiring.

SKILL.md

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B2B Sales Skill

Guide founders through designing, executing, and scaling B2B sales—from closing the first deal as a founder-seller to building a repeatable sales engine.

Reference Files

  • references/sales-process.md — Stage-by-stage sales process design with exit criteria
  • references/cold-outreach.md — Email sequences, call scripts, LinkedIn templates
  • references/demo-scripts.md — Demo frameworks and objection handling
  • references/proposals-sow.md — Proposal templates, SOW structure, pricing presentation
  • references/crm-selection.md — Tool-agnostic CRM guidance with selection criteria
  • references/pipeline-forecasting.md — Pipeline stages, metrics, forecasting models

Workflow

Step 1: Diagnose Stage & Sales Motion

Ask: "Where are you in your sales journey?"

StageSignalsFocus
Pre-salesNo paying customers, still validating→ Founder selling, discovery calls
First 10 customersClosing initial deals, learning process→ Sales process documentation
10-50 customersRepeatable motion emerging→ CRM setup, pipeline management
ScalingHiring first sales reps→ Playbook, forecasting, team

Sales Motion Selection:

Your ProductACV RangeRecommended Motion
Self-serve tool< $1KProduct-led, no sales needed
SMB SaaS$1K-$10KFounder-led → Inside sales
Mid-market$10K-$50KInside sales → AEs
Enterprise$50K+Field sales, solutions engineering

Step 2: Design Sales Process

Use references/sales-process.md for detailed guidance.

Core B2B Sales Stages:

StageGoalExit CriteriaTypical Duration
LeadIdentify fitResponded to outreach1-7 days
DiscoveryUnderstand painPain confirmed, budget exists1-2 calls
Demo/EvaluationShow valueChampion engaged, next steps1-3 weeks
ProposalPresent solutionProposal reviewed, feedback1-2 weeks
NegotiationAgree termsVerbal commitment1-4 weeks
Closed WonSigned dealContract executed

Stage-Appropriate Methodology:

SituationUse This Framework
Complex enterprise, multiple stakeholdersMEDDIC (Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, Champion)
Quick qualification, SMB dealsBANT (Budget, Authority, Need, Timeline)
Differentiated product, need to change behaviorChallenger Sale (Teach, Tailor, Take Control)
Relationship-heavy, consultative salesSPIN Selling (Situation, Problem, Implication, Need-payoff)
Early-stage, still learningStart simple, add methodology as you scale

Step 3: Build Outreach Engine

Use references/cold-outreach.md for templates.

Outreach Channel Effectiveness (B2B):

ChannelResponse RateBest For
Warm intro30-50%Any deal size, always prioritize
Personalized email5-15%Mid-market, enterprise
LinkedIn InMail10-25%Decision makers, executives
Cold call1-3% connectEnterprise, high ACV
Mass email1-2%SMB, volume play

Cold Email Sequence Structure:

EmailTimingFocus
Email 1Day 0Hook + specific value prop
Email 2Day 3Social proof or case study
Email 3Day 7Different angle + question
Email 4Day 14Breakup email

Key Outreach Metrics:

  • Open rate target: 40-60%
  • Reply rate target: 8-15%
  • Meeting book rate: 2-5% of outreach

Step 4: Master the Demo

Use references/demo-scripts.md for frameworks.

Demo Structure (30-45 min):

PhaseTimeActions
Rapport & Agenda3 minBuild connection, set expectations
Discovery Recap5 minConfirm pain points, goals
Demo15-20 minShow 3-4 key workflows, tie to their pain
Social Proof3 minRelevant customer stories
Pricing Overview5 minIf appropriate, or schedule follow-up
Q&A + Next Steps5-10 minHandle objections, book next meeting

Demo Principles:

  1. Show, don't tell — Live product beats slides
  2. Use their words — Reference what they said in discovery
  3. 3 features max — Deep on value, not feature tour
  4. Leave them wanting more — Don't show everything
  5. Always end with next steps — Never leave without commitment

Step 5: Close with Strong Proposals

Use references/proposals-sow.md for templates.

Proposal Structure:

SectionPurpose
Executive Summary1-page: Problem, solution, ROI, ask
Understanding Your ChallengesShow you listened in discovery
Proposed SolutionHow your product solves their problem
Implementation & TimelineWhat happens after they sign
Investment & ROIPricing with value justification
About UsCredibility, relevant customers
Next StepsClear path to "yes"

Pricing Presentation:

  • Always anchor high, then show value
  • Present 3 options when possible (Good/Better/Best)
  • Tie pricing to outcomes, not features
  • Include ROI calculation if possible

Step 6: Set Up Your CRM

Use references/crm-selection.md for detailed guidance.

CRM Selection by Stage:

StageRecommendationWhy
0-10 customersSpreadsheet or NotionFree, flexible, learn your process first
10-50 customersHubSpot Free/PipedriveEasy setup, good for founder-sellers
50-200 customersHubSpot Paid/Close/Salesforce EssentialsAutomation, reporting, team features
200+ customers / Enterprise dealsSalesforce / HubSpot EnterpriseCustomization, integrations, scale

CRM Selection Criteria:

FactorWeightQuestions
Ease of useHighWill reps actually use it?
Your sales motionHighMatches inbound vs outbound?
IntegrationsMediumWorks with your stack?
ReportingMediumGives insights you need?
PriceMediumFits budget as you scale?
CustomizationLow (early)Can grow with you?

Essential CRM Setup:

  1. Define pipeline stages (match your sales process)
  2. Set required fields per stage
  3. Create deal properties (ACV, close date, source)
  4. Build basic reports (pipeline, conversion, velocity)
  5. Integrate email for activity tracking

Step 7: Manage Pipeline & Forecast

Use references/pipeline-forecasting.md for detailed methods.

Pipeline Health Metrics:

MetricFormulaHealthy Range
Pipeline CoveragePipeline value ÷ Quota3-4x quota
Win RateWon deals ÷ Total deals20-30% (varies by ACV)
Sales CycleAvg days from lead to closeTrack by segment
Deal Velocity(# deals × win rate × ACV) ÷ cycleIncreasing MoM
Stage Conversion% moving to next stageDefine per stage

Forecasting Methods:

MethodHow It WorksBest For
Pipeline-basedSum of (deal value × probability)Early-stage, few deals
HistoricalBased on past conversion rates6+ months of data
Weighted pipelineStage-based probability weightsStandard approach
Bottoms-upRep-level commit + best caseLarger teams

Weekly Pipeline Review:

  1. Review each deal in negotiation stage
  2. Identify stuck deals (no activity > 14 days)
  3. Validate close dates and amounts
  4. Update forecast (commit, best case, pipeline)
  5. Identify gaps and plan outreach

Decision Checkpoints

When to Hire First Sales Rep

Ready to hire when:

  • Founder has closed 10+ deals personally
  • Sales cycle is understood and documented
  • Win rate is > 20%
  • Have 6+ months of pipeline data
  • Can articulate what "good" looks like

First hire profile:

  • Ideally: Previous startup experience at similar stage
  • Avoid: Big company reps who need infrastructure
  • Compensation: 50/50 base/commission typical for startups

When to Add Sales Methodology

Start simple, add complexity as needed:

Your SituationStart With
< $10K ACV, fast cycleSimple qualification checklist
$10K-$50K ACVBANT + basic discovery framework
> $50K ACV, multiple stakeholdersMEDDIC
Selling change, not just softwareChallenger principles

Deliverables

1. Sales Process Document

  • Stages with clear exit criteria
  • Key questions for each stage
  • Required CRM updates
  • Use docx skill for creation

2. Cold Outreach Sequence

  • 4-email sequence with templates
  • LinkedIn connection message
  • Call script for voicemail
  • Use docx skill for creation

3. Demo Script

  • Discovery recap template
  • Demo flow for 3-4 key features
  • Objection handling cheat sheet
  • Use docx skill for creation

4. Proposal Template

  • Customizable Word template
  • ROI calculator
  • Use docx skill for creation

5. Pipeline Tracker

  • Stage-based pipeline view
  • Forecast roll-up
  • Activity tracking
  • Use xlsx skill for creation

6. CRM Recommendation

  • Comparison of top options for their stage
  • Implementation checklist
  • Essential fields and stages

Common Sales Mistakes

Process Mistakes:

  1. No defined stages — Deals get stuck, no visibility
  2. Skipping discovery — Demo without understanding pain = low close rate
  3. Feature dumping — Showing everything instead of solving their problem
  4. No mutual action plan — Hoping vs. driving deals forward
  5. Single-threaded — Only one contact = deal dies when they leave

Outreach Mistakes:

  1. Too much "I/we" — Make it about them, not you
  2. No personalization — Generic = ignored
  3. Asking for too much — "30 min call" vs. "quick question"
  4. Giving up too early — Most responses come after 3+ touches
  5. No follow-up system — Leads fall through cracks

Forecasting Mistakes:

  1. Hoping vs. knowing — Commit only what you can defend
  2. Outdated close dates — Update weekly or forecast is fiction
  3. Ignoring stuck deals — If no activity for 2 weeks, it's not real
  4. Single best-case scenario — Always have commit/best case/pipeline

Integration with Other Skills

  • Use idea-validation skill first if ICP not validated
  • Use business-model skill for pricing strategy
  • Use go-to-market skill for overall GTM strategy
  • Use fundraising skill to pitch sales traction to investors
  • Use docx skill for sales collateral
  • Use xlsx skill for pipeline and forecast tracking

Adapted from Linas Beliūnas's The One-Person Unicorn founder skill set.

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