Skip to content
Back to skills

Keep Expand

ASecurity

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".

  • 2,719 stars
  • 0 votes
  • 0 copies
  • 1 view
  • Added September 21, 2026
ai-agentsbashapi

Works with

  • cli
  • api

Security analysis

A100/100

Scanned September 21, 2026

npx -y skills add jeremylongshore/claude-code-plugins-plus --skill keep-expand --agent claude-code

Installs into .claude/skills of the current project.

Are you the author of Keep Expand?

Add the live security badge to your README. It updates with every re-scan.

Security grade badge for Keep Expand
[![Security: A — Skills Directory](https://www.skillsdirectory.com/api/skills/jeremylongshore-keep-expand-4e2b3a87/badge)](https://www.skillsdirectory.com/skills/jeremylongshore-keep-expand-4e2b3a87)

More formats (shields.io, HTML) on the badges page. Keep it an A: scan every change in CI with Pro.

Download with Pro
SKILL.md
---
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".
allowed-tools: Read, Bash, Glob, Grep, AskUserQuestion
version: 0.1.0
author: tonone-ai <hello@tonone.ai>
license: MIT
---

# 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

```markdown
# 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.

Attribution

Is this your skill, or is something wrong with this listing? Request removal or report an issue. Author removals are honored within 72 hours.

Comments

Loading comments…

Newsletter

Get the weekly list of safe new skills, and the ones we pulled.