Self-healing content monitoring system that tracks freshness of all enablement assets, detects when content is stale, and triggers updates automatically. Use this skill whenever checking if enablement content is current, when a product change happens and assets need updating, when competitive landscape shifts, or when win rates drop (which may signal stale playbooks). Also trigger proactively when any enablement asset is older than 30 days, when a competitor makes news, when pricing changes, or when the user says "is our content up to date", "what needs refreshing", "we just launched a new feature", or "competitor just announced X". This is the self-healing engine that Matthew describes — content that knows when it's decaying.
Monitors enablement content for staleness, detects decay signals from CRM and competitive tools, and triggers updates or flags for review.
/plugin marketplace add https://www.claudepluginhub.com/api/plugins/jbalbu01-sales-enablement-2/marketplace.json/plugin install jbalbu01-sales-enablement-2@cpd-jbalbu01-sales-enablement-2This skill inherits all available tools. When active, it can use any tool Claude has access to.
The "self-healing" layer of the enablement system. Traditional enablement creates content once and hopes someone remembers to update it. This system actively monitors every asset, detects decay signals, and either auto-refreshes or flags content for human review.
Enablement content has a half-life:
If your battle card is 6 months old but your competitor shipped 3 features since then, the rep using that card is fighting with outdated intel.
┌─────────────────────────────────────────────────────────────────┐
│ CONTENT HEALTH │
├─────────────────────────────────────────────────────────────────┤
│ MONITORING LAYERS │
│ │
│ Layer 1: TIME-BASED │
│ • Track age of every asset in content-registry.md │
│ • Flag when assets exceed their freshness threshold │
│ • Escalate overdue assets in weekly health reports │
│ │
│ Layer 2: EVENT-DRIVEN │
│ • Product change → Flag all assets referencing old info │
│ • Competitor news → Flag related battle cards │
│ • Lost deal → Check if loss reason indicates stale content │
│ • Win rate drop → Investigate if playbook needs refresh │
│ │
│ Layer 3: OUTCOME-BASED │
│ • Track which content gets used and which doesn't │
│ • Identify assets with declining effectiveness │
│ • Surface "zombie content" that exists but nobody uses │
│ │
│ RESPONSE │
│ • Auto-refresh: Update with new data (competitive intel, etc.) │
│ • Flag for review: Alert human when judgment needed │
│ • Propagate changes: When one thing changes, update downstream │
├─────────────────────────────────────────────────────────────────┤
│ SUPERCHARGED (when you connect your tools) │
│ + ~~CRM: Win rate trends that signal playbook decay │
│ + ~~CRM: Lost deal reasons that expose content gaps │
│ + ~~CRM: Deal stage conversion drops flagging stale process │
│ + ~~competitive intel (ZoomInfo): Competitor tech stack changes │
│ + ~~competitive intel (ZoomInfo): New competitor product launches│
│ + ~~competitive intel (Clay): Company signal changes │
│ + ~~competitive intel (LinkedIn): Competitor hiring & news │
│ + ~~conversation intelligence (Gong): Objection frequency shifts│
│ + ~~conversation intelligence (Gong): Talk track effectiveness │
│ + ~~chat: Rep feedback on stale or missing content │
└─────────────────────────────────────────────────────────────────┘
CRITICAL: Before generating a health report from the registry alone, pull live data from connected tools to detect decay signals that time-based tracking misses.
Check if you have access to CRM tools (look for tools containing search_crm_objects, get_crm_objects, or similar).
If CRM tools ARE available:
deals for Closed Won and Closed Lost in the last 30-60 days.
dealname, amount, dealstage, closedate, closed_lost_reason, closed_won_reason, pipelinecompetitors.md.
ZoomInfo (if available):
zoominfo_search_company on competitors listed in competitors.md.
zoominfo_search_company to validate current ICP definition.
Clay (if available):
clay_enrich_company on key competitors for recent changes.
LinkedIn (if available):
linkedin_search_companies for competitor updates.
linkedin_search_leads to validate persona definitions.
Check if you have access to Gong tools (look for tools prefixed with gong_).
If Gong tools ARE available:
gong_search_calls to compare objection patterns over last 30 vs prior 30 days.
gong_get_call_stats for top performers vs team average.
gong_search_calls with competitor names.
If chat tools are available (slack_search_public, slack_search_public_and_private):
"Content health scan complete. [N] decay signals detected from live data: [If CRM:] Win rate dropped [X]% in last 30 days — flagging playbook for review. [N] deals lost to [Competitor] not in our battle cards. [If Gong:] New objection '[objection]' appearing in [N] calls — not in objection library. [If ZoomInfo:] [Competitor] announced [change] — battle card is [N] days stale. [If Slack:] [N] reps flagged content issues in the last month. Running full health report now..."
After the auto-pull, ask ONLY for what the tools couldn't provide:
Build using ALL evidence. Combine time-based decay (from content-registry.md) with event-driven signals (from tools). Cite sources: "Per CRM:", "Per Gong:", "Per ZoomInfo:", "Per Slack:", "Per content-registry.md:". Prioritize actions by severity × business impact.
content-registry.md with current freshness scores incorporating tool datamemory/competitors.md with any new competitive intel discoveredmemory/deal-patterns.md with new win/loss patternsmemory/changelog.mdEvery enablement asset is tracked in memory/content-registry.md:
| Asset | Type | Created | Last Updated | Freshness Score | Max Age | Dependencies | Auto-Refresh? |
|-------|------|---------|-------------|-----------------|---------|-------------|---------------|
| Battle Card: CompA | battle-card | 2026-01-15 | 2026-01-15 | 🟢 95/100 | 30 days | competitors.md | Yes |
| Enterprise Playbook | playbook | 2025-12-01 | 2026-01-10 | 🟡 62/100 | 90 days | product.md, icp.md | No — needs review |
| SDR Discovery Guide | discovery | 2025-11-15 | 2025-11-15 | 🔴 28/100 | 60 days | icp.md | Yes |
Base Score: 100 (at creation/update)
Decay factors:
- Time: -1 point per day beyond 50% of max age
- Event-triggered: -20 points per relevant product/competitor change
- Outcome-based: -10 points if win rate in related deals drops >5%
- Usage: -15 points if asset hasn't been referenced in 30 days
Freshness thresholds:
🟢 70-100: Current — no action needed
🟡 40-69: Aging — schedule refresh within 2 weeks
🔴 0-39: Stale — refresh immediately or retire
When the user reports a product change (new feature, pricing update, positioning shift):
product.md as a dependencyExample:
User: "We just raised our pricing by 15%" System: "Updated product.md. Flagging 4 assets for refresh: ROI Calculator (auto-refreshing now), Proposal Template (needs your review — value framing may change), Battle Card: CompA (auto-refreshing pricing comparison), Enterprise Playbook (pricing section needs manual update)."
When competitive news is detected (via scheduled monitoring or user input):
When a deal is won or lost:
Generated on demand or via scheduled automation:
# Enablement Content Health Report
**Date:** [Today]
**Total Assets:** [N]
**Health Distribution:** 🟢 [N] current | 🟡 [N] aging | 🔴 [N] stale
---
## Immediate Action Required (🔴 Stale)
| Asset | Age | Last Event | Recommended Action |
|-------|-----|-----------|-------------------|
| [Asset] | [X] days | [What triggered staleness] | [Refresh / Retire / Review] |
## Schedule Refresh (🟡 Aging)
| Asset | Freshness | Estimated Effort | Skill to Use |
|-------|-----------|-----------------|-------------|
| [Asset] | [Score]/100 | [Quick / Medium / Deep] | [battle-cards / playbook-builder / etc.] |
## Recently Refreshed
| Asset | Updated | By | Change |
|-------|---------|-----|--------|
| [Asset] | [Date] | [Auto / Manual] | [What changed] |
---
## Trends
- Content freshness trend: [Improving / Stable / Declining]
- Most frequently updated: [Asset] — [Why it changes often]
- Zombie content (exists but unused): [List]
- Missing content (gaps identified): [List]
When one piece of knowledge changes, the system traces downstream dependencies:
Product pricing changes
↓
├── ROI Calculator → Auto-refresh calculations
├── Proposal Template → Flag pricing section
├── Battle Card: CompA → Refresh pricing comparison
├── Playbook → Flag pricing objection section
└── Objection Library → Update "too expensive" responses
This is tracked via the Dependencies column in the content registry. Each asset declares what it depends on, and changes propagate through the dependency graph.
This skill works with scheduled shortcuts:
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