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Agent skill

Keep Expand

by jeremylongshore in jeremylongshore/tons-of-skills-marketplace

Design expansion revenue playbooks — upsell triggers, seat expansion sequences, tier upgrade paths, and cross-sell motions.

MITAuto-check: notes

Install Keep Expand

skills CLI
$ npx skills add jeremylongshore/tons-of-skills-marketplace --skill keep-expand -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install jeremylongshore/tons-of-skills-marketplace keep-expand --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/jeremylongshore/tons-of-skills-marketplace.git skills-src && mkdir -p .claude/skills && cp -r skills-src/plugins/ai-agency/tonone/skills/keep-expand .claude/skills/keep-expand && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
keep-expand
GitHub stars
2.8k
Token cost
~1.4k tokens
SKILL.md length
347 words
Files
1
Skills in repo
3,342
Repo updated
First seen
Licence
MIT

At a glance

Design expansion revenue playbooks — upsell triggers, seat expansion sequences, tier upgrade paths, and cross-sell motions.

  • Works in 6 steps: Expansion Prerequisites Check → Map Expansion Levers → Design Expansion Trigger System → …
  • Asked to grow existing customers
  • SKILL.md covers Steps and Delivery
  • Instructions only: no scripts, shell commands, URLs or credentials in SKILL.md

What it does

Keep Expand is an agent skill from jeremylongshore/tons-of-skills-marketplace. 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".

Its SKILL.md is about 1.4k tokens, which your agent loads only when the skill is triggered. It is a single SKILL.md file with no bundled scripts.

The repository describes itself as: Model-agnostic agent-skills platform with a harness-free canonical layer, verified adapters, and the ccpi package manager. Explore at tonsofskills.com. The licence is MIT.

When your agent uses it

  • Asked to grow existing customers
  • How do we get customers to expand

Example prompts

  • “grow existing customers”
  • “increase NRR”
  • “design upsell”
  • “/keep-expand”

Requirements

  • Pre-approved tools (allowed-tools): Read, Bash, Glob, Grep, AskUserQuestion

Workflow steps

6 steps, taken from the step headings in SKILL.md.

  1. Expansion Prerequisites Check
  2. Map Expansion Levers
  3. Design Expansion Trigger System
  4. Write Expansion Conversation Guides
  5. Produce Expansion Playbook
  6. Escalation Path

What it can do on your machine

Read from SKILL.md and the folder at commit cfae287. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves these tools, so the agent can use them without asking each time:

    • Read
    • Bash
    • Glob
    • Grep
    • AskUserQuestion

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    No scripts in the folder and no shell commands in SKILL.md (its code samples are markdown).

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    No URLs in SKILL.md.

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

Context cost

Keep Expand loads about 1.4k tokens when it runs. Until then it costs about 63 tokens; SKILL.md has 347 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~63
When it runs · the whole SKILL.md, loaded when a task matches
~1.4k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check: notes

The automated check noted patterns worth knowing about, such as sudo or a known installer.

  • NotePre-approves every shell command (allowed-tools: Bash)SKILL.md
    allowed-tools: Read, Bash, Glob, Grep, AskUserQuestion

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from jeremylongshore/tons-of-skills-marketplace at commit cfae287, republished under its MIT licence (© jeremylongshore). 347 words, ~1,361 tokens.

Download SKILL.mdSave it as .claude/skills/keep-expand/SKILL.md (or your agent's skills folder).
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
LeverDescriptionTrigger Signal
Seat expansionAdd more usersTeam invite attempts, sharing behavior
Tier upgradeMove to higher planHitting limits, using premium features
Usage upsellMore volume/API callsApproaching usage ceiling
Add-on purchaseAdjacent featureUsing workaround for missing capability
Cross-sellDifferent productICP fit + different use case pain
Multi-yearLonger contractStable, high satisfaction, budget cycle
Step 2: Design Expansion Trigger System

For each lever, define:

LeverTrigger conditionWho detectsWhen to actConversation opener
Seat expansion3+ non-user stakeholders mentionedCSMWithin 1 week"I noticed you mentioned your team — want to loop them in?"
Tier upgrade80% of tier limit hitSystem alertProactively, 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:

BlockerResponse
"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.

© jeremylongshore, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

Just SKILL.md in plugins/ai-agency/tonone/skills/keep-expand of jeremylongshore/tons-of-skills-marketplace.

Open the folder on GitHubat commit cfae287

Compare with similar skills

Keep Expand next to the 5 skills that share the most tags, products or categories with it. Stars are the repository's; “used in” counts other GitHub owners with a copy.

Keep Expand compared with similar skills
SkillStarsUsed inTokensAuto-checkLicenceRepo updated
Keep Expand this skilljeremylongshore/tons-of-skills-marketplace2.8k—~1.4kAutomated safety check: NotesMIT
Modeling Revenue MetricsPostHog/posthog40k—~2.1kAutomated safety check: PassCustom licence
Expansion Playbookgtmagents/gtm-agents4141 repos~318Automated safety check: PassApache-2.0
Expansion Retentiontech-leads-club/agent-skills7k—~5.6kAutomated safety check: PassCustom licence
Intl Expansionalirezarezvani/claude-skills28k1 repos~1.1kAutomated safety check: PassMIT
Text Expansionthedaviddias/Front-End-Checklist74k—~534Automated safety check: PassMIT

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  • Expansion Playbook

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Questions about Keep Expand

What does Keep Expand do?

Design expansion revenue playbooks — upsell triggers, seat expansion sequences, tier upgrade paths, and cross-sell motions. Keep Expand is an agent skill from jeremylongshore/tons-of-skills-marketplace. Design expansion revenue playbooks — upsell triggers, seat expansion sequences, tier upgrade paths, and cross-sell motions.

When should I use Keep Expand?

Keep Expand fits situations like: asked to grow existing customers; how do we get customers to expand.

How do I install Keep Expand in Claude Code?

Run `npx skills add jeremylongshore/tons-of-skills-marketplace --skill keep-expand -a claude-code`. Or copy the skill folder (plugins/ai-agency/tonone/skills/keep-expand in jeremylongshore/tons-of-skills-marketplace) into .claude/skills/keep-expand in your project. Claude Code loads it when a task matches its description.

How do I install Keep Expand in Codex?

Run `npx skills add jeremylongshore/tons-of-skills-marketplace --skill keep-expand -a codex`. Or copy the skill folder (plugins/ai-agency/tonone/skills/keep-expand in jeremylongshore/tons-of-skills-marketplace) into .agents/skills/keep-expand in your project. Codex loads it when a task matches its description.

Can I use Keep Expand in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add jeremylongshore/tons-of-skills-marketplace --skill keep-expand -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/keep-expand, .gemini/skills/keep-expand, .github/skills/keep-expand and .opencode/skills/keep-expand in your project.

What does Keep Expand need to run?

SKILL.md names no scripts, command-line tools or credentials: Keep Expand is instructions for the agent only. Its frontmatter pre-approves these tools: Read, Bash, Glob, Grep, AskUserQuestion.

Does Keep Expand access the network?

SKILL.md contains no URLs. Any network use would come from the scripts or tools the agent runs. This is read from the text; nothing was executed.

Is Keep Expand safe to install?

Our automated static check of SKILL.md found notes only (pre-approves every shell command (allowed-tools: bash)), nothing it rates as a warning. It is not a guarantee. Review the folder before installing.

What licence does Keep Expand use?

Keep Expand is published under the MIT licence (declared in SKILL.md). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does Keep Expand use?

About 1.4k tokens (SKILL.md is roughly 5.4k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full.

What are the alternatives to Keep Expand?

Skills that share tags, products or a category with Keep Expand: Modeling Revenue Metrics (PostHog/posthog, 40k stars), Expansion Playbook (gtmagents/gtm-agents, 414 stars), Expansion Retention (tech-leads-club/agent-skills, 7k stars) and Intl Expansion (alirezarezvani/claude-skills, 28k stars). The comparison table on this page puts their stars, adoption, token cost, safety result and licence side by side.

Who maintains Keep Expand?

jeremylongshore (a GitHub user) maintains it in jeremylongshore/tons-of-skills-marketplace, which has 2,827 GitHub stars. The repository holds 3,342 skills in this directory. The repository was last updated on October 10, 2026.

Source: jeremylongshore/tons-of-skills-marketplace on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.