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afrexai-sales-playbook
Complete B2B sales system — from ICP to closed-won. Discovery frameworks, objection handling, pipeline management, forecasting, and deal acceleration. Works for any B2B company.
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byopenclaw
Installation
Claude Code / Cursor / Codex
$curl -o ~/.claude/skills/afrexai-sales-playbook/SKILL.md --create-dirs "https://raw.githubusercontent.com/openclaw/skills/main/skills/1kalin/afrexai-sales-playbook/SKILL.md"
Manual Installation
- Download SKILL.md from GitHub
- Place it in
.claude/skills/afrexai-sales-playbook/SKILL.mdinside your project - Restart your AI agent — it will auto-discover the skill
How afrexai-sales-playbook Compares
| Feature / Agent | afrexai-sales-playbook | Standard Approach |
|---|---|---|
| Platform Support | multi | Limited / Varies |
| Context Awareness | High | Baseline |
| Installation Complexity | Unknown | N/A |
Frequently Asked Questions
What does this skill do?
Complete B2B sales system — from ICP to closed-won. Discovery frameworks, objection handling, pipeline management, forecasting, and deal acceleration. Works for any B2B company.
Which AI agents support this skill?
This skill is compatible with multi.
Where can I find the source code?
You can find the source code on GitHub using the link provided at the top of the page.
SKILL.md Source
# B2B Sales Playbook ⚡
**The complete system for running a repeatable, scalable B2B sales operation.**
Not a CRM wrapper. Not a template collection. This is a full sales methodology — from identifying your ideal customer to closing the deal and expanding the account.
---
## Phase 1: Ideal Customer Profile (ICP) & Territory
### ICP Definition Template
```yaml
icp:
company:
industry: [SaaS, Fintech, Healthcare, etc.]
size_employees: [50-500]
size_revenue: [$5M-$50M ARR]
geography: [US, UK, DACH, etc.]
tech_stack: [signals they use tools you integrate with]
growth_stage: [Series A-C, post-PMF, scaling]
pain_indicators: # Observable signals, not assumptions
- hiring_for: [roles that signal the pain you solve]
- tech_adoption: [recently adopted X tool = need for Y]
- org_changes: [new VP of X = budget for initiatives]
- regulatory: [upcoming compliance deadline]
- public_statements: [earnings call mentions, press releases]
buyer_personas:
economic_buyer: # Signs the check
title_patterns: [VP Sales, CRO, CEO]
cares_about: [revenue growth, cost reduction, competitive advantage]
speaks_in: [ROI, board metrics, market share]
champion: # Fights for you internally
title_patterns: [Director, Head of, Senior Manager]
cares_about: [team productivity, career advancement, solving daily pain]
speaks_in: [workflow, efficiency, team capacity]
technical_evaluator: # Validates feasibility
title_patterns: [Engineering Manager, Architect, IT Director]
cares_about: [integration, security, maintenance burden]
speaks_in: [APIs, uptime, migration effort]
end_user: # Uses it daily
title_patterns: [Individual contributors]
cares_about: [ease of use, time saved, fewer context switches]
anti-signals: # DO NOT pursue
- company_size_under: 20 # too small, long sales cycle for low ACV
- no_budget_indicator: [startup pre-revenue, recent layoffs >30%]
- tech_mismatch: [on-prem only, legacy stack incompatible]
- cultural: [committee-driven decisions with 6+ stakeholders at low ACV]
```
### Territory Planning
**Account Tiering:**
| Tier | Criteria | Accounts | Time Allocation | Touch Frequency |
|------|----------|----------|-----------------|-----------------|
| **Tier 1** | Perfect ICP fit + active pain signals | 20-30 | 50% of time | 2-3x/week |
| **Tier 2** | Good ICP fit, no active signals yet | 50-80 | 30% of time | 1x/week |
| **Tier 3** | Partial fit, worth monitoring | 100-200 | 15% of time | 2x/month |
| **Inbound** | Any qualified inbound | Variable | 5% of time | Respond <1hr |
**Monthly Territory Review:**
1. Re-score all Tier 1 accounts — any demote to Tier 2?
2. Scan Tier 2 for new signals — any promote to Tier 1?
3. Remove dead accounts from Tier 3 (no engagement in 90 days)
4. Add new accounts from prospecting
5. Calculate territory coverage: (accounts with activity / total) — target >80% for Tier 1
---
## Phase 2: Prospecting & Outreach
### Multi-Channel Sequence Framework
**Principle:** No single channel works. Layer them.
**Standard Tier 1 Sequence (14 days):**
| Day | Channel | Action | Goal |
|-----|---------|--------|------|
| 1 | Email | Personalized cold email (see template below) | Open + reply |
| 1 | LinkedIn | View profile + connect (NO pitch in connect msg) | Warm the name |
| 3 | Email | Follow-up with value add (article, insight, data) | Demonstrate expertise |
| 5 | LinkedIn | Comment on their recent post (genuine, not salesy) | Build familiarity |
| 7 | Phone | Cold call (see script below) | Live conversation |
| 7 | Email | Voicemail follow-up email | Multi-touch reinforcement |
| 10 | LinkedIn | Send message referencing your email/call attempts | Channel switch |
| 12 | Email | Breakup email (creates urgency) | Force response |
| 14 | Phone | Final attempt | Last touch |
**Sequence Rules:**
- STOP the sequence the moment they reply (positive OR negative)
- Never send more than 1 email per day to the same person
- Personalization must reference something SPECIFIC (their company, role, recent news)
- If they open but don't reply 3x → they're reading, switch to phone
- If zero engagement after full sequence → move to Tier 3, retry in 90 days
### Cold Email Templates
**Template 1: The Trigger Event**
```
Subject: [Trigger event] → quick thought
[First name],
Saw [specific trigger — new hire, funding, product launch, earnings mention].
When [companies in their situation] hit this stage, [specific problem] usually becomes the bottleneck — [data point or example].
[One sentence on how you solve this, tied to the trigger.]
Worth a 15-min call to see if this applies to [company]?
[Your name]
```
**Template 2: The Peer Reference**
```
Subject: How [similar company] solved [problem]
[First name],
[Similar company in their industry] was dealing with [specific problem] — [quantify: X hours/week, $Y lost, Z% error rate].
They [brief result: cut X by 40%, saved $Y/month, shipped Z days faster].
Happy to share what they did differently — no pitch, just the playbook.
15 min this week?
[Your name]
```
**Template 3: The Breakup**
```
Subject: Closing the loop
[First name],
I've reached out a few times about [problem/topic] — I'll assume the timing isn't right.
If [problem] becomes a priority later, I'm here.
Deleting your reminder from my CRM now.
[Your name]
```
**Why breakup emails work:** 30-40% reply rate. People respond to loss aversion. "Deleting your reminder" creates fear of losing access.
### Cold Call Script
**Opening (first 10 seconds decide everything):**
```
"Hi [Name], this is [You] from [Company].
Did I catch you at an okay time?"
[If yes:]
"I'll be brief. I noticed [trigger/signal] and wanted to ask —
are you currently dealing with [specific problem]?"
[If they confirm the problem:]
"Got it. What's that costing you right now — in time, money, or headaches?"
[Let them talk. Take notes. Ask follow-up questions.]
"That's exactly what we help with. [One sentence proof point.]
Would it make sense to set up 20 minutes this week to dig into this properly?"
```
**Common cold call responses + rebuttals:**
| They Say | You Say |
|----------|---------|
| "Not interested" | "Totally fair — can I ask, is it because [problem] isn't a priority, or you've already solved it?" |
| "Send me an email" | "Happy to — what specifically would be most useful to include? That way I don't waste your time." |
| "We already have a solution" | "Good — how's it working? Most companies I talk to have something in place but still have gaps in [specific area]." |
| "Bad timing" | "When would be better? I can put a reminder in for [suggested date]." |
| "How did you get my number?" | "LinkedIn / your website. I know cold calls aren't fun — I'll keep it under 2 minutes." |
---
## Phase 3: Discovery — The Most Important Meeting
### MEDDPICC Qualification Framework
Score each element 1-3 (1=unknown, 2=partially known, 3=fully confirmed):
```yaml
deal_qualification:
metrics: # Quantifiable impact they care about
score: [1-3]
detail: "[What numbers matter? Revenue increase, cost reduction, time saved?]"
source: "[Who told you? Validated how?]"
economic_buyer: # Person with budget authority
score: [1-3]
name: "[Name and title]"
access: "[Have you spoken to them directly?]"
priority: "[Is this in their top 3 priorities?]"
decision_criteria: # How they'll evaluate options
score: [1-3]
technical: "[Integration, security, performance requirements]"
business: "[ROI threshold, payback period, risk tolerance]"
political: "[Internal politics, competing priorities]"
decision_process: # How they'll make the decision
score: [1-3]
steps: "[What happens between now and signed contract?]"
timeline: "[When do they need to decide? Hard deadline?]"
stakeholders: "[Who's involved? Who has veto power?]"
paper_process: # Legal/procurement steps
score: [1-3]
procurement: "[Standard terms or custom negotiation?]"
legal_review: "[How long does legal take? Past precedent?]"
security_review: "[Required? How long?]"
identified_pain: # The problem driving this
score: [1-3]
pain: "[What hurts? What breaks?]"
impact: "[Cost of inaction — quantified]"
urgency: "[Why now? What happens if they wait?]"
champion: # Your internal advocate
score: [1-3]
name: "[Who is it?]"
motivation: "[Why do THEY personally care?]"
power: "[Can they influence the economic buyer?]"
coached: "[Have you prepped them for internal selling?]"
competition: # What you're up against
score: [1-3]
competitors: "[Named competitors in the evaluation]"
status_quo: "[Doing nothing is always a competitor]"
differentiation: "[Why you win against each]"
total_score: "[X/24]"
# 20-24 = Strong deal, forecast confidently
# 15-19 = Gaps to fill, work the unknowns
# 10-14 = At risk, needs significant work
# <10 = Unqualified, don't invest time
```
### Discovery Questions by Category
**Situation (understand current state):**
1. Walk me through how [process] works today, start to finish.
2. What tools/systems are involved?
3. How many people touch this process?
4. How long has it been this way?
**Problem (surface the pain):**
5. Where does it break down?
6. What's the impact when it fails? (Get a NUMBER)
7. How often does that happen?
8. What have you tried to fix it?
9. Why didn't that work?
**Implication (expand the pain):**
10. If this doesn't get fixed in the next 6 months, what happens?
11. How does this affect [their boss / their team / the company]?
12. What's the cost of doing nothing? (Force them to quantify)
13. What other initiatives depend on solving this?
**Need-Payoff (let THEM sell the solution):**
14. If you could wave a magic wand, what would this look like?
15. What would it mean for your team if [pain] went away?
16. If you could get [specific metric improvement], what would that unlock?
17. How would [their boss] react to those results?
**Process (map the buying journey):**
18. Besides you, who else needs to weigh in on this?
19. What's happened before when you've bought software like this?
20. Is there a budget allocated, or would this need approval?
21. What's the ideal timeline for having this running?
22. What would kill this deal?
### Discovery Call Structure (30 min)
| Segment | Time | What You Do |
|---------|------|-------------|
| Opening | 2 min | Confirm agenda, set expectations, get permission to ask questions |
| Context | 5 min | Ask situation questions — understand their world |
| Pain | 10 min | Ask problem + implication questions — go DEEP on 1-2 pains |
| Vision | 5 min | Ask need-payoff questions — paint the future state |
| Process | 5 min | Map decision process, timeline, stakeholders |
| Next Steps | 3 min | Agree on SPECIFIC next action with date |
**Golden Rule:** Talk <30% of the time. If you're talking more, you're pitching, not discovering.
---
## Phase 4: Demo & Presentation
### The Problem-Solution-Proof Framework
Never demo features. Demo outcomes.
**Structure:**
1. **Mirror their pain** (2 min) — "You told me [specific pain from discovery]. Here's what that costs you: [quantified impact]."
2. **Show the solution** (15 min) — Walk through their USE CASE, not a generic tour. Use THEIR data, THEIR terminology, THEIR workflow.
3. **Prove it works** (5 min) — Case study of similar company. Before/after numbers. "Company X had the same problem. Here's what happened."
4. **Address risks** (3 min) — Proactively surface the top concern they haven't raised yet. "Most companies at your stage worry about [X]. Here's how we handle that."
5. **Next step** (2 min) — Never end without a committed next action.
### Demo Anti-Patterns
| ❌ Don't | ✅ Do Instead |
|----------|---------------|
| Show every feature | Show only what maps to their pain |
| Start with "let me share my screen" | Start with "let me recap what you told me" |
| Say "and we also do..." | Say "you mentioned [pain] — here's exactly how that works" |
| Demo to the whole committee at once | Demo to champion first, then do joint session |
| Let the demo run long | End 5 min early — scarcity signals confidence |
| Send a recording after | Send a 1-page summary with their specific ROI |
### Mutual Action Plan (MAP)
After demo, create a shared doc with the prospect:
```yaml
mutual_action_plan:
deal: "[Company Name] + [Your Company]"
target_go_live: "[Date]"
steps:
- step: "Technical deep-dive with engineering team"
owner: "[Prospect technical contact]"
date: "[Date]"
status: pending
- step: "Security review / questionnaire"
owner: "[You — send completed questionnaire]"
date: "[Date]"
status: pending
- step: "Business case presentation to [Economic Buyer]"
owner: "[Champion + You]"
date: "[Date]"
status: pending
- step: "Proposal / pricing review"
owner: "[You]"
date: "[Date]"
status: pending
- step: "Legal / contract review"
owner: "[Prospect legal]"
date: "[Date]"
status: pending
- step: "Signature"
owner: "[Economic Buyer]"
date: "[Date]"
status: pending
- step: "Kickoff call"
owner: "[Your CS team]"
date: "[Date]"
status: pending
```
**Why MAPs work:** Shared accountability. Visible timeline. Champion can use it to drive internal momentum. You can reference specific dates when things stall.
---
## Phase 5: Objection Handling
### The LAER Framework
Every objection follows this pattern:
1. **Listen** — Let them finish. Don't interrupt. Nod.
2. **Acknowledge** — "That's a fair concern" / "I hear you" (NOT "I understand but...")
3. **Explore** — "Help me understand — is it [X] specifically, or more about [Y]?" (Diagnose the REAL objection)
4. **Respond** — Address the real concern, not the surface one.
### Objection Playbook
**Price Objections:**
| Objection | Real Meaning | Response |
|-----------|-------------|----------|
| "Too expensive" | They don't see the value yet | "Compared to what? Help me understand what you're measuring against." Then re-anchor to cost of doing nothing. |
| "Can you do a discount?" | Testing your confidence | "Our pricing reflects the value we deliver. [Company X] saw [Y result] — the ROI was [Z]x. What specifically feels misaligned?" |
| "We don't have budget" | Not a priority OR wrong buyer | "Is this a timing issue, or is [problem] not a priority this quarter?" If priority: "When budgets reset, can we plan for that?" |
| "Competitor is cheaper" | Using you for leverage OR genuinely price-sensitive | "They may be. The question is what [missing capability] costs you over 12 months. Would you like me to map that out?" |
**Timing Objections:**
| Objection | Real Meaning | Response |
|-----------|-------------|----------|
| "Not now, maybe next quarter" | No urgency | "What changes next quarter? If [problem] costs you [X/month], that's [3X] by next quarter. What would it take to move this up?" |
| "We're in the middle of [other project]" | Genuinely busy OR smokescreen | "Totally get it. When does [project] wrap? Let's lock in a date now so it doesn't slip." |
| "We need to think about it" | Unresolved concern they haven't voiced | "Of course. What specifically do you need to think through? I might be able to address it now." |
**Authority Objections:**
| Objection | Real Meaning | Response |
|-----------|-------------|----------|
| "I need to run this by my boss" | You're not talking to the decision-maker | "Absolutely. What's their biggest concern likely to be? Let's prep for that together." Then: "Would it help if I joined that conversation?" |
| "Our committee decides" | Multi-stakeholder deal | "Who's on the committee? What does each person care about most? Let's make sure the proposal speaks to all of them." |
**Status Quo Objections:**
| Objection | Real Meaning | Response |
|-----------|-------------|----------|
| "We're fine with what we have" | Fear of change > desire for improvement | "How long have you had it? What's changed in your business since then? Most companies I talk to outgrow [current solution] when they hit [their growth stage]." |
| "We built our own" | Pride in internal solution | "That's impressive. What's the maintenance cost? Most teams I talk to find their engineers are spending [X%] of time maintaining instead of building product." |
### The "Negative Reverse" Technique
When objections keep coming, flip the script:
> "It sounds like this might not be the right fit. Should we just call it?"
This does two things:
1. Takes pressure off — they stop defending
2. Forces them to either agree (you saved time) or sell THEMSELVES on why it IS a fit
---
## Phase 6: Closing & Negotiation
### Closing Signals (When to Ask)
**Verbal:**
- "What would implementation look like?"
- "How does pricing work?"
- "Can we do a pilot?"
- "What's the contract length?"
- "When could we start?"
**Behavioral:**
- They introduce you to additional stakeholders
- They ask for references
- They share internal documents/requirements
- Response time gets faster
- They start using "we" and "when" instead of "if"
### Closing Techniques
**1. The Summary Close**
```
"So to recap — [problem] is costing you [X/month], you need a solution
by [date] for [reason], and [your product] addresses [their top 3 criteria].
Shall I send the agreement?"
```
**2. The Next Step Close**
```
"Based on everything we've discussed, the next step would be
[specific action — contract review, pilot setup, intro to CS].
Should I kick that off?"
```
**3. The Assumptive Close**
```
"Great — I'll have the proposal over by end of day.
Would you prefer monthly or annual billing?"
```
**4. The Puppy Dog Close (for hesitant buyers)**
```
"Tell you what — let's do a 14-day pilot with [specific use case].
You'll see [expected result] in the first week.
If it doesn't deliver, no hard feelings. Fair?"
```
### Negotiation Rules
1. **Never negotiate against yourself.** If they ask for a discount, ask what they'd give in return (longer term, case study, referral, faster signature).
2. **Trade, don't cave.** Every concession must get something back.
3. **Anchor high.** Start with your full price. The first number sets the range.
4. **Silence is power.** After stating your price, STOP TALKING. Let them respond.
5. **Know your walk-away.** Before any negotiation, set your floor. Below that = no deal.
6. **Bundle value, don't discount price.** Add a month free, add training, add premium support — don't cut the sticker price.
7. **Create deadline.** "This pricing is valid through [date]" or "I have 2 onboarding slots left this quarter."
### Discount Decision Tree
```
Prospect asks for discount
├── Do they have budget?
│ ├── YES → Don't discount. Anchor to value.
│ └── NO → Is the deal strategic (logo, case study, expansion potential)?
│ ├── YES → Offer trade: discount for [annual commit / case study / referral]
│ └── NO → Walk away or defer to next quarter
├── Is this a competitive situation?
│ ├── YES → Don't discount on price. Win on value + risk reduction.
│ └── NO → They're testing. Hold firm. "Our pricing reflects..."
└── Final rule: NEVER discount more than 20% on any deal.
Below that, you're training them to negotiate hard every renewal.
```
---
## Phase 7: Pipeline Management
### Pipeline Stages & Exit Criteria
| Stage | Definition | Exit Criteria | Probability |
|-------|-----------|---------------|-------------|
| **Prospecting** | Initial outreach, no meeting yet | Meeting booked | 5% |
| **Discovery** | First meeting held | Pain confirmed, ICP match validated | 15% |
| **Evaluation** | Active evaluation, demo delivered | Champion identified, decision criteria known | 30% |
| **Proposal** | Proposal/pricing sent | Budget confirmed, decision process mapped | 50% |
| **Negotiation** | Terms being discussed | Verbal commit, legal/procurement started | 75% |
| **Closed Won** | Contract signed | ✅ Revenue recognized | 100% |
| **Closed Lost** | Deal lost | Reason documented, next steps noted | 0% |
**Stage Hygiene Rules:**
- No deal stays in a stage for more than 2x the average time for that stage
- Every deal must have a next step with a date
- If a deal has no activity for 14 days → flag for review
- Update stages based on BUYER actions, not your actions (you sending a proposal ≠ Proposal stage; them REVIEWING it does)
### Weekly Pipeline Review Template
```yaml
pipeline_review:
date: "[YYYY-MM-DD]"
summary:
total_pipeline: "$[X]"
weighted_pipeline: "$[X]"
new_this_week: [X deals, $Y]
advanced_this_week: [X deals moved forward]
closed_won: [X deals, $Y]
closed_lost: [X deals, $Y — reasons]
slipped: [X deals pushed from this month]
deals_to_review: # Top 10 by size
- company: "[Name]"
value: "$[X]"
stage: "[Stage]"
age_in_stage: "[X days]"
next_step: "[Action]"
risk: "[red/yellow/green]"
risk_reason: "[Why]"
actions:
- "[Deal]: [Specific action to take this week]"
pipeline_health:
coverage_ratio: "[X]x" # Pipeline / Quota — target 3-4x
avg_deal_size: "$[X]"
avg_sales_cycle: "[X days]"
win_rate: "[X%]"
stage_conversion:
discovery_to_eval: "[X%]"
eval_to_proposal: "[X%]"
proposal_to_closed: "[X%]"
```
### Forecast Categories
| Category | Definition | Rules |
|----------|-----------|-------|
| **Commit** | WILL close this period | Verbal yes, contract in legal, no blockers |
| **Best Case** | High probability this period | Champion pushing, decision process active, some risk |
| **Pipeline** | Could close this period, needs work | In evaluation, not yet at proposal stage |
| **Upside** | Unlikely this period but possible | Early stage, right ICP, uncertain timeline |
**Forecast Accuracy Rule:** Your commit number should be within 10% of actual. If it's consistently off, your qualification is broken.
---
## Phase 8: Deal Acceleration Tactics
### When Deals Stall — Diagnostic Checklist
```
Deal is stalled. Ask yourself:
1. [ ] Do I have a champion? (If no → find one or walk away)
2. [ ] Have I talked to the economic buyer? (If no → get access)
3. [ ] Is there a compelling event / deadline? (If no → create urgency)
4. [ ] Do they understand the cost of doing nothing? (If no → quantify it)
5. [ ] Are there unresolved objections? (If yes → LAER them)
6. [ ] Is there a competitor blocking? (If yes → differentiate or reframe)
7. [ ] Is my champion still engaged? (If no → re-engage with new value)
8. [ ] Have I multi-threaded? (If no → engage other stakeholders)
```
### Multi-Threading Strategy
**Rule:** Never have just one contact in a deal. If your champion leaves, gets sick, or goes on vacation — your deal dies.
**Minimum contacts by deal size:**
- <$25K ACV → 2 contacts (champion + economic buyer)
- $25K-$100K → 3-4 contacts (champion, economic buyer, technical evaluator, end user)
- $100K+ → 5+ contacts (add: procurement, legal, executive sponsor)
### Urgency Creation (Ethical)
| Technique | How | When to Use |
|-----------|-----|-------------|
| **Cost of delay** | "Every month this isn't solved costs you $[X]. That's $[3X] by Q[next]." | When they have no timeline |
| **Capacity constraint** | "We're onboarding 3 clients this quarter. After that, next slot is [date]." | When true (never lie) |
| **Price timeline** | "Current pricing is locked through [date]." | When price changes are planned |
| **Competitive risk** | "Your competitor [name] just signed with us." | When true and relevant |
| **Regulatory deadline** | "[Regulation] takes effect [date]. You need [X weeks] to implement." | When compliance is a factor |
---
## Phase 9: Post-Sale & Expansion
### Handoff to Customer Success
```yaml
deal_handoff:
company: "[Name]"
closed_date: "[Date]"
contract_value: "$[X] / [term]"
key_contacts:
- name: "[Champion]"
role: "[Title]"
communication_preference: "[email/slack/phone]"
personality: "[detail-oriented/big picture/hands-on]"
- name: "[Executive Sponsor]"
role: "[Title]"
engagement_level: "[high/medium/low]"
success_metrics: "[What they told you success looks like]"
context:
pain_points_solved: "[List from discovery]"
promised_outcomes: "[Specific commitments made during sales]"
known_risks: "[Anything that could cause churn]"
expansion_opportunity: "[What else they could buy]"
competitor_considered: "[Who else they evaluated and why they chose you]"
implementation:
priority_use_cases: "[What to set up first]"
technical_requirements: "[Integrations, SSO, data migration]"
timeline_expectations: "[What you committed to]"
DO_NOT:
- "[Any sensitive topics to avoid]"
- "[Things that were contentious during sales]"
```
### Expansion Revenue Playbook
**When to upsell (signals):**
- Usage hits >80% of their current tier/limit
- They ask about features in higher tiers
- New team/department asks to join
- They hit a milestone (growing headcount, new market)
- Renewal is 90 days away (bundle expansion with renewal)
**Expansion conversation:**
```
"I noticed [specific usage signal]. That usually means [outcome they care about]
is going well.
Other companies at your stage typically [expand to X / add Y] to [benefit].
Would it make sense to explore that?"
```
**Never upsell:**
- When they have unresolved support issues
- During the first 60 days
- When they're at risk of churning
- Without data showing they'll get value from the expansion
---
## Phase 10: Metrics & Self-Improvement
### Activity Metrics (Leading Indicators)
| Metric | Target | Why It Matters |
|--------|--------|---------------|
| Outbound emails/day | 30-50 | Pipeline generation |
| Calls/day | 15-25 | Pipeline generation |
| Meetings booked/week | 8-12 | Pipeline conversion |
| Discovery calls/week | 5-8 | Qualified pipeline |
| Demos/week | 3-5 | Active evaluation |
| Proposals sent/week | 2-3 | Close to money |
### Outcome Metrics (Lagging Indicators)
| Metric | Formula | Healthy Range |
|--------|---------|---------------|
| Win rate | Won / (Won + Lost) | 20-35% |
| Avg deal size | Total revenue / Deals closed | Trending up |
| Sales cycle | Avg days from first touch to close | Trending down |
| Pipeline coverage | Open pipeline / Quota | 3-4x |
| Activity-to-meeting ratio | Meetings / (Emails + Calls) | >5% |
| Meeting-to-opportunity ratio | Opportunities / Meetings | >50% |
| Forecast accuracy | Actual / Committed | >90% |
### Win/Loss Analysis Template
```yaml
deal_analysis:
company: "[Name]"
outcome: "[Won/Lost]"
value: "$[X]"
cycle_length: "[X days]"
won_because: # or lost_because
- "[Primary reason]"
- "[Secondary reason]"
competitor: "[Who they went with / considered]"
what_worked:
- "[Specific thing that moved the deal forward]"
what_didnt:
- "[Specific mistake or gap]"
lesson:
- "[What to do differently next time]"
process_score: # Self-assessment
prospecting: [1-5]
discovery: [1-5]
demo: [1-5]
objection_handling: [1-5]
closing: [1-5]
relationship: [1-5]
```
### Monthly Self-Review Questions
1. What's my win rate trend? (Improving, flat, declining)
2. Where do deals die most? (Which stage has the biggest drop-off)
3. Am I talking to the right people? (Economic buyer access rate)
4. Are my deals getting bigger or smaller?
5. What objection am I weakest at handling?
6. Which outreach channel converts best for me?
7. Am I spending time on the right deals? (80/20 — are 80% of results from 20% of deals?)
8. What did I learn from my last 3 losses?
---
## Natural Language Commands
| Command | What It Does |
|---------|-------------|
| "Build my ICP" | Walk through ICP definition template |
| "Write outreach for [company]" | Generate personalized multi-channel sequence |
| "Prep me for discovery with [company]" | Build discovery question set based on what you know |
| "Qualify this deal" | Run MEDDPICC assessment with scoring |
| "Help me handle [objection]" | Pull relevant playbook + practice response |
| "Review my pipeline" | Generate weekly pipeline review |
| "Why am I losing deals?" | Run win/loss analysis on recent losses |
| "Forecast this quarter" | Categorize deals into commit/best case/pipeline/upside |
| "Prep a proposal for [company]" | Generate proposal based on discovery notes |
| "Write a follow-up after [meeting type]" | Generate appropriate follow-up email |
| "Coach me on [call recording/notes]" | Analyze a sales conversation and give feedback |
| "How do I close [company]?" | Assess deal state and recommend closing strategy |