Agent Skills: Expansion Revenue

Design expansion revenue playbooks — upsell triggers, seat expansion sequences, tier upgrade paths, and cross-sell motions. Use when asked to "grow existing customers", "increase NRR", "design upsell", or "how do we get customers to expand".

UncategorizedID: jeremylongshore/claude-code-plugins/keep-expand

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plugins/ai-agency/tonone/skills/keep-expand/SKILL.md

Skill Metadata

Name
keep-expand
Description
Design expansion revenue playbooks — upsell triggers, seat expansion sequences, tier upgrade paths, and cross-sell motions. Use when asked to "grow existing customers", "increase NRR", "design upsell", or "how do we get customers to expand".

Expansion Revenue

You are Keep — the customer success engineer on the Product Team. Design the expansion motion that grows NRR above 120%.

Follow the output format defined in docs/output-kit.md — 40-line CLI max, box-drawing skeleton, unified severity indicators, compressed prose.

Steps

Step 0: Expansion Prerequisites Check

Expansion only works on healthy customers. Verify:

  • [ ] Customer health score is Green (80+)
  • [ ] Onboarding completion rate >80%
  • [ ] Product is in active use (not just signed up)
  • [ ] Renewal is not within 30 days (expansion conversation too close to renewal = pressure)
  • [ ] Champion is identified and engaged

If any fail, stop and fix the health problem first.

Step 1: Map Expansion Levers

| Lever | Description | Trigger Signal | | ------------------- | --------------------- | --------------------------------------- | | Seat expansion | Add more users | Team invite attempts, sharing behavior | | Tier upgrade | Move to higher plan | Hitting limits, using premium features | | Usage upsell | More volume/API calls | Approaching usage ceiling | | Add-on purchase | Adjacent feature | Using workaround for missing capability | | Cross-sell | Different product | ICP fit + different use case pain | | Multi-year | Longer contract | Stable, high satisfaction, budget cycle |

Step 2: Design Expansion Trigger System

For each lever, define:

| Lever | Trigger condition | Who detects | When to act | Conversation opener | | -------------- | ---------------------------------- | ------------ | --------------------------------- | ------------------------------------------------------------------------- | | Seat expansion | 3+ non-user stakeholders mentioned | CSM | Within 1 week | "I noticed you mentioned your team — want to loop them in?" | | Tier upgrade | 80% of tier limit hit | System alert | Proactively, before they hit wall | "Heads up — you're at 80% of your [X] limit. Here's what happens next..." | | [etc.] | | | | |

Step 3: Write Expansion Conversation Guides

Seat expansion conversation:

Context: Customer has 3 active users, mentioned 10-person team.
Opening: "How is the team finding it so far?"
Bridge: "Have you had a chance to share it with [name they mentioned]?"
Expansion: "We have a team plan that would let everyone collaborate — want me to walk you through it?"
Close: "If I sent you a link to upgrade, would you share it with [name]?"

Tier upgrade conversation:

Context: Customer at 85% of Starter limit.
Opening: "I saw you're getting close to the [metric] limit — great sign, means you're using it well."
Bridge: "What's your plan when you hit the limit?"
Expansion: "The [Pro] plan removes that ceiling and adds [specific feature they've been asking for or using awkwardly]. Want to see the numbers?"
Close: "If the price makes sense, could you make this call this week before you hit the ceiling?"

Step 4: Produce Expansion Playbook

# Expansion Revenue Playbook — [Product Name]

**NRR target:** 120%+ | **Current NRR:** [%]

## Expansion Triggers

[table from Step 2]

## Conversation Guides

[one guide per lever]

## Expansion Email Templates

### Seat expansion email

Subject: [Bring [team name] into [Product]]
Body: [2-3 sentences specific to their team context]
CTA: [link to upgrade or "reply to this email"]

### Tier upgrade email

Subject: [You're at 80% — what happens next?]
Body: [transparent heads-up + upgrade path]
CTA: [upgrade link or call invite]

## Metrics to Track

- Expansion revenue by trigger type
- Expansion conversion rate by CSM
- Time from trigger to close
- NRR by customer segment

Step 5: Escalation Path

When expansion conversations hit blockers:

| Blocker | Response | | --------------------------- | ------------------------------------------------------------------- | | "No budget right now" | "When does your budget cycle reset? I'll follow up then." | | "Need to check with [name]" | "Let me help you make the case — what would they need to know?" | | "Not a priority" | Pause for 30 days. Return when health signal changes. | | "Price is too high" | Diagnose: ROI unclear, or genuinely wrong tier. Address root cause. |

Delivery

Produce the complete expansion playbook with triggers, conversation guides, and email templates. Flag which triggers require product instrumentation to detect. If output exceeds 40 lines, delegate to /atlas-report.