HubSpot Pipeline Cleanup

Overview

A messy CRM pipeline destroys forecast accuracy, demoralizes reps ("everything looks stuck"), and hides real opportunities. This skill walks the user through a systematic pipeline audit that identifies which deals to close, push, or escalate — based on objective rules, not gut feel.

Core principle: A deal that hasn't moved stages in 2x the average sales cycle for that stage is either dead or being neglected. Treat it as dead until proven otherwise.

The 4-quadrant deal classification

For every open deal, classify into one quadrant:

Definitions:

• "Recent activity" = email logged, call logged, meeting completed, or stage change
• "Avg time in stage" = your historical average for that pipeline stage. If unknown, default: Qualification 14d, Demo 21d, Proposal 14d, Negotiation 21d

Workflow

Step 1: Ask the user for context

1. Which pipeline are we cleaning? (Sales / Customer Success / Partnerships / Other)
2. What's your typical sales cycle (in days)?
3. Any deals you already know are dead?
4. Date of last formal pipeline review?

If user says "I don't know my sales cycle" → use defaults from references/sales-velocity-benchmarks.md.

Step 2: Pull the deal list

Ask user to export from HubSpot:

• All open deals
• Columns: Deal Name, Stage, Amount, Close Date, Last Modified Date, Last Contacted Date, Owner, Stage Entry Date

Save as CSV. If user pastes the list, parse it directly.

Step 3: Classify each deal

For each deal, compute:

days_in_current_stage = today - stage_entry_date
days_since_activity   = today - last_contacted_date
stage_health          = days_in_current_stage / avg_time_for_stage

if stage_health < 2 and days_since_activity ≤ 14:  HEALTHY
if stage_health < 2 and days_since_activity > 14:  NUDGE
if stage_health ≥ 2 and days_since_activity ≤ 14:  STUCK
if stage_health ≥ 2 and days_since_activity > 14:  DEAD

Step 4: Surface the cleanup actions

For each category, recommend specific actions:

🟢 HEALTHY — No action. List them only.

🟡 NUDGE — One-liner per deal: "Email [Contact] re: [last context]". Group by owner.

🟠 STUCK — These need a coach-the-rep conversation. Surface the pattern:

• "3 deals stuck in 'Proposal' for owner X" → maybe rep struggles closing
• "5 deals stuck in 'Demo' across pipeline" → maybe demo doesn't convert; root-cause it

🔴 DEAD — Recommend close-lost with reason. Ask user to confirm before bulk-closing.

Step 5: Forecast clean-up impact

After classification, show:

Pipeline before cleanup: $X across N deals
After removing DEAD: $Y across M deals (more accurate forecast)
Recovered hours: estimated X hours/month rep time wasted on dead deals

The "close-lost reason" trap

HubSpot's default close-lost reasons are too generic ("No decision", "Went with competitor"). They tell you nothing.

Push for specifics:

• ❌ "Lost to competitor" → ✅ "Lost to [Competitor] — they had [specific feature/price]"
• ❌ "Budget" → ✅ "Budget — wanted to stay <$X, our floor was $Y"
• ❌ "Timing" → ✅ "Timing — wanted to wait for [event/quarter]"

See references/close-lost-taxonomy.md for the actionable taxonomy.

Quarterly cleanup ritual

This skill should run every quarter at minimum. Suggest the user calendar:

1. Week 1 of quarter: cleanup (this skill)
2. Week 2: rep 1:1s on stuck deals
3. Week 12: forecast finalization (informed by clean pipeline)

Red flags

• >40% of pipeline is "DEAD" → systemic issue: leads-quality, qualification process, or rep behavior
• Average deal age > 2x sales cycle → forecast is fiction; pipeline coverage ratio meaningless
• One owner has 3x the dead-deal rate → coaching opportunity, not a "lazy rep" judgment
• Recent activity = "task created" only → activity theater, not real engagement
• Deals reopening multiple times → poor qualification at top of funnel

Quick reference

What NOT to do

• Don't mass-close-lost without rep review — you might kill a real deal
• Don't change ownership during cleanup — does more harm than good mid-quarter
• Don't add new mandatory fields during cleanup — pile-on; do it next quarter
• Don't use AI to write the rep coaching message — the rep needs to own the relationship