/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
code
/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
code
/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:
code
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:
code
# 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:
code
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:
code
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:
code
list_findings({
eventTypes: ["DEAL_WON", "DEAL_LOST"],
dateRange: { start: "<period start>", end: "<today>" }
})
Step 4: Present Analysis
Full Win/Loss Report
code
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)
code
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)
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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:
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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:
- •CRM integration isn't syncing deal outcomes
- •Date range has no closed deals
- •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:pmm- Create battlecards from competitive insights - •
/octave:research- Research for current pipeline deals