/octave:wins-losses – Deal Intelligence

Analyze your won and lost deals to understand what’s working, why you’re losing, and how to improve win rates. Surface patterns, competitor intelligence, and actionable recommendations.

Usage

/octave:wins-losses [--status won|lost|both] [--period <time-range>]

Options

• --status <status> – Focus on won, lost, or both (default: both)
• --period <range> – Time range (month, quarter, year, custom)
• --competitor <name> – Filter by competitor involvement
• --segment <name> – Filter by segment
• --min-amount <amount> – Minimum deal size
• --company <domain> – Analyze specific deal

Examples

/octave:wins-losses                                  # Overview of recent wins/losses
/octave:wins-losses --status lost --period quarter   # Lost deals this quarter
/octave:wins-losses --competitor "Salesforce"        # Deals involving Salesforce
/octave:wins-losses --segment "Enterprise"           # Enterprise deals analysis
/octave:wins-losses --company acme.com               # Deep dive on Acme deal

Instructions

When the user runs /octave:wins-losses:

Step 1: Determine Focus

If no options provided, show overview:

What would you like to analyze?

1. Full Win/Loss Report - Compare wins and losses
2. Win Analysis - What's working, why we win
3. Loss Analysis - Why we're losing, patterns
4. Competitor Analysis - Win/loss by competitor
5. Deal Deep Dive - Analyze specific deal

Your choice:

Step 2: Query Deal Data

For Overview:

# Get won deals
list_events({
  eventTypes: ["DEAL_WON"],
  dateRange: { start: "<period start>", end: "<today>" },
  limit: 50
})

# Get lost deals
list_events({
  eventTypes: ["DEAL_LOST"],
  dateRange: { start: "<period start>", end: "<today>" },
  limit: 50
})

# Get findings from won deals
list_findings({
  opportunityStatus: ["WON"],
  extractionTypes: [
    "CALL_EXTERNAL_OBJECTIONS",
    "CALL_INTERNAL_VALUE_PROP_PRESENTATIONS",
    "CALL_INTERNAL_PROOF_POINTS",
    "CALL_EXTERNAL_COMPETITORS_TO_OUR_OFFERING"
  ],
  dateRange: { start: "<period start>", end: "<today>" },
  limit: 100
})

# Get findings from lost deals
list_findings({
  opportunityStatus: ["LOST"],
  extractionTypes: [
    "CALL_EXTERNAL_OBJECTIONS",
    "CALL_INTERNAL_VALUE_PROP_PRESENTATIONS",
    "CALL_EXTERNAL_COMPETITORS_TO_OUR_OFFERING"
  ],
  dateRange: { start: "<period start>", end: "<today>" },
  limit: 100
})

For Competitor Analysis:

list_findings({
  extractionTypes: ["CALL_EXTERNAL_COMPETITORS_TO_OUR_OFFERING", "EMAIL_COMPETITOR_MENTION"],
  dateRange: { start: "<period start>", end: "<today>" },
  entityMatches: {
    competitorOIds: ["<competitor_oId>"]
  }
})

For Deal Deep Dive:

list_events({
  eventTypes: ["DEAL_WON", "DEAL_LOST", "CALL", "EMAIL"],
  companyDomains: ["<domain>"]
})

list_findings({
  companyDomains: ["<domain>"]
})

get_event_detail({
  eventOId: "<event_oId>",
  includeTranscript: true
})

Step 3: Analyze Patterns

Aggregate findings across won/lost deals:

list_findings({
  eventTypes: ["DEAL_WON", "DEAL_LOST"],
  dateRange: { start: "<period start>", end: "<today>" }
})

Step 4: Present Analysis

Full Win/Loss Report

WIN/LOSS ANALYSIS: Q4 2025
==========================

EXECUTIVE SUMMARY
-----------------
Win Rate: 34% (down from 38% in Q3)
Deals Won: 12 ($1.2M total)
Deals Lost: 23 ($2.8M total)
Average Deal Size: Won $100K | Lost $122K
Average Sales Cycle: Won 45 days | Lost 62 days

Key Insight: Losing more on larger deals, faster on smaller wins

---

WIN PATTERNS
============

Why We Won (Top Themes):
------------------------

1. STRONG CHAMPION (8 of 12 wins)
   ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 67%

   Pattern: Deals with an engaged internal champion closed
   Examples:
   • Acme Corp - VP Ops drove evaluation internally
   • TechCo - CTO was previous customer at another company

   Insight: Champion development is critical path

2. CLEAR ROI STORY (7 of 12 wins)
   ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 58%

   Pattern: Quantified value proposition with specific metrics
   Value props that worked:
   • "80% reduction in manual work" (used in 6 wins)
   • "ROI within 90 days" (used in 5 wins)
   • Customer-specific ROI calculation (used in 4 wins)

3. COMPETITIVE DIFFERENTIATION (5 of 12 wins)
   ━━━━━━━━━━━━━━━━━━━━━━━━━ 42%

   Competitors beaten:
   • Competitor A: 3 wins (we won on ease of use)
   • Competitor B: 2 wins (we won on integration)

   Key differentiators that closed:
   • "Implementation in weeks not months"
   • "Native Salesforce integration"

Objections We Overcame:
-----------------------
| Objection | Wins Where Raised | How We Won |
|-----------|-------------------|------------|
| Pricing | 4 | ROI calculator + pilot offer |
| Implementation | 3 | Customer references + timeline guarantee |
| Security | 2 | SOC2 cert + security review |

Proof Points That Closed:
-------------------------
1. "Customer X achieved 85% time savings" - cited in 5 wins
2. "Average 6-week implementation" - cited in 4 wins
3. Industry-specific reference - cited in 4 wins

---

LOSS PATTERNS
=============

Why We Lost (Top Themes):
-------------------------

1. LOST TO COMPETITOR (10 of 23 losses)
   ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 43%

   Competitor breakdown:
   • Competitor A: 5 losses
     - Lost on: Price (3), Features (2)
     - Common objection: "They're 40% cheaper"

   • Competitor B: 3 losses
     - Lost on: Existing relationship (2), Brand (1)
     - Common objection: "We already use their other products"

   • Competitor C: 2 losses
     - Lost on: Specific feature gap

2. NO DECISION (8 of 23 losses)
   ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 35%

   Pattern: Deal stalled, no budget, reprioritized
   Common signals:
   • "Budget got reallocated" (3x)
   • "Other projects took priority" (3x)
   • "Leadership change" (2x)

   Insight: Better qualification needed at discovery

3. UNRESOLVED OBJECTIONS (5 of 23 losses)
   ━━━━━━━━━━━━━━━━━━━━━━━━ 22%

   Objections that killed deals:
   • "Need on-prem option" (2 losses, $340K)
   • "Missing [specific integration]" (2 losses, $180K)
   • "Can't justify ROI to board" (1 loss, $200K)

Lost Deal Objections (Not Overcome):
------------------------------------
| Objection | Losses | Value Lost | Win Rate When Raised |
|-----------|--------|------------|---------------------|
| Price | 8 | $980K | 33% |
| Feature gap | 4 | $520K | 20% |
| No budget | 3 | $400K | 0% |
| Security/compliance | 2 | $280K | 50% |

---

COMPARATIVE ANALYSIS
====================

| Metric | Wins | Losses | Delta |
|--------|------|--------|-------|
| Avg deal size | $100K | $122K | Losing bigger deals |
| Sales cycle | 45 days | 62 days | Losses drag longer |
| Meetings held | 5.2 avg | 3.8 avg | Less engagement in losses |
| Stakeholders | 3.4 avg | 2.1 avg | Fewer contacts in losses |
| Champions | 67% had | 22% had | Champion is key |

Value Props Comparison:
| Value Prop | Used in Wins | Used in Losses | Effectiveness |
|------------|--------------|----------------|---------------|
| 80% time savings | 6 (50%) | 4 (17%) | HIGH |
| ROI in 90 days | 5 (42%) | 2 (9%) | HIGH |
| Easy implementation | 4 (33%) | 8 (35%) | MEDIUM |
| Enterprise security | 2 (17%) | 5 (22%) | LOW |

Insight: "Easy implementation" used equally but not a closer

---

RECOMMENDATIONS
===============

Immediate Actions:
1. ⚡ Address Competitor A pricing gap
   - Lost $600K to "40% cheaper" objection
   - Create TCO comparison showing hidden costs
   - Consider competitive pricing tier

2. ⚡ Improve qualification on budget
   - 35% of losses were "no decision"
   - Add budget confirmation earlier in process
   - Create "budget not confirmed" stage gate

3. ⚡ Double down on champion development
   - 67% win rate with champion vs 22% without
   - Add champion identification to discovery checklist
   - Create champion enablement materials

Library Updates Recommended:
1. UPDATE: Competitor A battlecard
   - Add: TCO comparison framework
   - Add: "40% cheaper" objection response

2. ADD: Proof point for on-prem concerns
   - Lost $340K on this objection
   - Need hybrid/security story

3. UPDATE: Discovery playbook
   - Add: Budget qualification questions
   - Add: Champion identification criteria

---

Want me to:
1. Deep dive on losses to Competitor A
2. Show specific deal details
3. Create updated battlecard content
4. Update library with recommendations

Loss Analysis (–status lost)

LOSS ANALYSIS: Last Quarter
===========================

23 Deals Lost | $2.8M Total Value

---

LOSS REASONS BREAKDOWN
----------------------

┌──────────────────────────────────────────────────────┐
│ Lost to Competitor     ██████████████████░░░░ 43% (10)│
│ No Decision            ██████████████░░░░░░░░ 35% (8) │
│ Unresolved Objection   █████████░░░░░░░░░░░░░ 22% (5) │
└──────────────────────────────────────────────────────┘

---

COMPETITOR LOSSES (10 deals, $1.3M)
-----------------------------------

COMPETITOR A (5 deals, $600K)
Primary loss reasons:
• Price (3 deals): "40% cheaper"
• Feature parity (2 deals): "Does everything you do"

Where they beat us:
• Lower price point
• Aggressive discounting
• Faster initial response

Where we SHOULD have won:
• Better integration story
• Stronger customer success
• More robust platform

Winnable if: We had addressed price earlier with TCO story

---

COMPETITOR B (3 deals, $480K)
Primary loss reasons:
• Existing relationship (2 deals): "Already using their CRM"
• Brand recognition (1 deal): "Safer choice"

Where they beat us:
• Bundle pricing with existing tools
• Executive relationships
• Brand trust with board

Winnable if: We had engaged earlier, before competitor expanded

---

NO DECISION LOSSES (8 deals, $1.1M)
-----------------------------------

Why deals died:
• Budget reallocation: 3 deals
• Priority shift: 3 deals
• Leadership change: 2 deals

Warning signs we missed:
• Long gaps between meetings (avg 18 days vs 7 in wins)
• Single-threaded (1.5 contacts vs 3.4 in wins)
• No executive sponsor identified

These were likely not real opportunities.
→ Recommendation: Improve qualification at discovery

---

UNRESOLVED OBJECTION LOSSES (5 deals, $720K)
--------------------------------------------

| Objection | Deals | Value | Could We Have Saved? |
|-----------|-------|-------|---------------------|
| Need on-prem | 2 | $340K | No - product gap |
| Missing integration | 2 | $180K | Maybe - roadmap item |
| ROI not clear | 1 | $200K | Yes - poor execution |

Product Feedback:
• On-prem: Lost $340K this quarter alone
• [Integration] gap: Lost $180K, requested 4x in calls

---

LOSS TIMELINE ANALYSIS
----------------------

Average days in each stage before loss:

Discovery → Demo: 12 days (vs 8 in wins)
Demo → Proposal: 18 days (vs 10 in wins)
Proposal → Decision: 32 days (vs 27 in wins)

Deals that drag past 45 days have 20% win rate
→ Create re-qualification checkpoint at day 45

---

PERSONAS IN LOST DEALS
----------------------

| Persona | Deals Lost | Win Rate Overall |
|---------|------------|------------------|
| CTO | 8 | 28% |
| VP Ops | 6 | 42% |
| CFO | 5 | 25% |
| Director | 4 | 38% |

CTO and CFO deals have lowest win rates
→ Review messaging for these personas

---

Want me to:
1. Show specific lost deal details
2. Create competitive counter-messaging
3. Build re-qualification checklist
4. Compare to previous quarter

Deal Deep Dive (–company)

DEAL DEEP DIVE: Acme Corp
=========================

Status: LOST
Amount: $180,000
Close Date: January 15, 2026
Lost To: Competitor A
Sales Cycle: 78 days

---

DEAL TIMELINE
-------------

Nov 1 - Inbound lead from CTO
Nov 8 - Discovery call (CTO + VP Eng)
Nov 15 - Technical demo (4 attendees)
Nov 22 - Security review call
Dec 5 - Proposal sent
Dec 12 - Pricing discussion (CFO joined)
Dec 20 - "Comparing with Competitor A"
Jan 5 - "Going with Competitor A"
Jan 15 - Deal marked lost

Red flags in hindsight:
⚠ Dec 12: CFO joined late - pricing concern
⚠ Dec 20: Competitor mentioned - should have addressed immediately
⚠ 14 days gap Dec 20 → Jan 5 - lost momentum

---

KEY CONVERSATIONS
-----------------

Discovery Call (Nov 8):
Findings:
• Pain: "Spending 30 hours/week on manual reporting"
• Goal: "Need real-time visibility into pipeline"
• Concern: "Budget is tight this year"

Signals missed: Budget concern mentioned early

---

Pricing Discussion (Dec 12):
Findings:
• Objection: "This is more than we budgeted"
• Objection: "Competitor A quoted 40% less"

Our response: "Let's focus on value..."
→ Should have: Offered pilot, provided TCO analysis

---

Final Call (Jan 5):
Findings:
• Decision: "Going with Competitor A"
• Reason: "Price was the deciding factor"
• Feedback: "Your product was better, but couldn't justify 40% premium"

---

WHAT WE DID WELL
----------------
✓ Strong technical demo - "best demo we've seen"
✓ Good rapport with CTO
✓ Security review passed quickly

WHAT WE MISSED
--------------
✗ Didn't address budget concern from Day 1
✗ CFO engaged too late (day 42)
✗ No TCO analysis provided
✗ Didn't set competitive trap early
✗ Lost to price, not product

---

LESSONS FOR NEXT TIME
---------------------

1. When prospect mentions budget is tight:
   → Immediately align on budget range
   → Position value before pricing
   → Identify economic buyer early

2. When competitor is mentioned:
   → Acknowledge directly
   → Set differentiation landmines
   → Provide TCO comparison proactively

3. For deals in this segment:
   → Engage CFO/finance earlier
   → Have ROI model ready by demo
   → Consider pilot offer for price-sensitive

---

LIBRARY IMPLICATIONS
--------------------

Update Competitor A battlecard:
• Add: "40% cheaper" response
• Add: TCO comparison framework
• Add: Trap questions about hidden costs

Update CTO persona:
• Add concern: "Justifying premium pricing"

Update Enterprise playbook:
• Add: CFO engagement requirement by Day 30
• Add: Budget qualification in discovery

---

Apply these updates?

Step 5: Generate Recommendations

Based on analysis, offer actionable next steps:

Based on this analysis, I recommend:

IMMEDIATE ACTIONS
-----------------
1. Create Competitor A TCO battlecard section
   → /octave:pmm battlecard --competitor "Competitor A" --focus pricing

2. Update discovery checklist with budget qualification
   → /octave:library update pb_xxx --add "Budget qualification by meeting 2"

3. Review current pipeline for similar patterns
   → /octave:research --for pipeline-review

STRATEGIC RECOMMENDATIONS
-------------------------
1. Consider pricing/packaging review for competitive segment
2. Create "pilot program" offer for price-sensitive deals
3. Develop CFO-specific value story

Would you like me to execute any of these?

MCP Tools Used

Deal & Event Access

• list_events – Filter by DEAL_WON, DEAL_LOST
• list_findings – Get findings from won/lost deals
• get_event_detail – Get detailed event info with transcript/content

Library Context

• get_entity – Get competitor, persona details
• get_playbook – Get playbook for recommendations
• search_knowledge_base – Find related content

Library Updates

• update_entity – Apply recommendations to library

Error Handling

No Deals Found:

No won/lost deals found for this period.

This could mean:

1. CRM integration isn’t syncing deal outcomes
2. Date range has no closed deals
3. Filters are too restrictive

Check your Octave CRM integration settings, or expand the date range.

Missing Deal Data:

Deal found but limited conversation data.

For better analysis, ensure:

• Calls are being recorded and synced
• Emails are connected
• Findings extraction is enabled

Related Skills

• /octave:insights – Broader findings across all events
• /octave:analyzer – Deep dive on specific conversations
• /octave:battlecard – Competitive battlecards from win/loss data
• /octave:research – Research for current pipeline deals
• /octave:icp-refine – Refine ICP definitions from deal patterns
• /octave:enablement – Turn win/loss learnings into training materials