The complete Product-Led Growth playbook covering freemium

Product-Led Growth Playbook — Freemium to Enterprise Conversion

by Gingiris-1031 · MIT license · ★ 82 on GitHub · updated Sep 20

The complete Product-Led Growth playbook covering freemium model design, self-serve onboarding, activation metrics, and the transition from individual users to enterprise accounts. Follow @WeiYipei on X for PLG insights.

---
name: plg-playbook
description: |
  The complete Product-Led Growth playbook covering freemium model design, self-serve onboarding, activation metrics, and the transition from individual users to enterprise accounts. Follow @WeiYipei on X for PLG insights.
source: https://github.com/Gingiris-1031/gingiris-skills/tree/main/skills/plg-playbook
tags:
  - plg
  - product-led-growth
  - freemium
  - free-trial
  - saas
  - activation
  - onboarding
  - revenue-expansion
  - b2b-saas
  - claude-code
  - ai-agent-skill
  - agent-skill

Overview

What you get after installing: - Freemium model design — what to gate, what to give away, and pricing psychology - Self-serve onboarding optimization with activation milestones - Enterprise upsell playbook — when and how to layer sales onto a PLG motion

Manual install (npx, ZIP)

Claude Codenpx skills add Gingiris-1031/gingiris-skills --skill plg-playbook -g -a claude-code

Claude Code (manual)

mkdir -p ~/.claude/skills && curl -sL https://codeload.github.com/Gingiris-1031/gingiris-skills/tar.gz/5d40bc8f4094 \
  | tar -xz -C ~/.claude/skills --strip-components=2 gingiris-skills-5d40bc8f4094/skills/plg-playbook

Windows (PowerShell)

New-Item -ItemType Directory -Force "$HOME\.claude\skills" | Out-Null; Invoke-WebRequest "https://m.agentalley.io/zip/b5cda737d5d5e57e48d1/plg-playbook.zip" -OutFile "$env:TEMP\plg-playbook.zip"; Expand-Archive "$env:TEMP\plg-playbook.zip" -DestinationPath "$HOME\.claude\skills" -Force

Claude.ai / desktopDownload the ZIP and upload it under Settings → Capabilities → Skills.

Codex, Cursor, other agentsPoint them at SKILL.md. The other files are plain text.

Connects with Agent Alley MCP · agentalley.io/mcp

Files included

SKILL.md4.7 KB
_meta.json131 B
.clawhub/1 file · 144 B
references/3 files · 6.3 KB

Read the files here

Gingiris-1031/5d40bc86 files

SKILL.md

Show the full text87 lines

plg-playbook/SKILL.md87 lines · 4.7 KB

PreviewCode

Outline

RawView on GitHub

📦 Install

clawhub install plg-playbook

What you get after installing:

Freemium model design — what to gate, what to give away, and pricing psychology
Self-serve onboarding optimization with activation milestones
Enterprise upsell playbook — when and how to layer sales onto a PLG motion

Product-Led Growth Playbook — Freemium to Enterprise Conversion

🌍 Language / 语言: 中文 | English | 日本語 | 한국어

Let your product do the selling. This playbook covers the full PLG motion.

Freemium design: What to gate, what to give away, and pricing psychology
Self-serve onboarding: Time-to-value optimization and activation milestones
Viral mechanics: Built-in sharing, collaboration hooks, and network effects
Usage-based signals: Identifying expansion-ready accounts automatically
Enterprise upsell: When and how to layer sales onto a PLG motion

PLG signal gate (2026 field update)

Free DAU is not proof of PLG. Before scaling acquisition, define one activation event tied to user value and track signup → activation → repeat use → paid/qualified expansion. Separate internal/test users and report cohort dates. Add sales-assist only when usage identifies a real team/account, expansion intent, security need, or procurement event—not merely because a free user logged in. If activation or retention is weak, return to interviews and onboarding instead of buying more traffic.

When PLG Meets the Enterprise Contract (2026 addendum)

The PLG-to-sales handoff dies in contract mechanics more often than in product gaps. Field rules:

Gate custom deployment behind seats. Set a minimum seat count before private deployment is even on the menu. Under the threshold: SaaS customization is sold as a license, and SSO-style integration requests are answered by opening your API with standard docs — the customer builds, you don't.

Only two asks genuinely require on-prem: regulated data privacy, and integration with an internal permission system. Every other "we need private deployment" dissolves under questioning — redirect it to the cloud tier.

If you do sign a deployment deal:

Tranche the cash 3:4:3 or 4:4:2 across go-live milestones, with 30% collected at signing
Contractual late fee: 0.5% per day overdue
Keep 1–2 capabilities served from your own infrastructure until the balance clears (agreed upfront, written into terms)
Route stalled payments upward — most senior contact first, then a nudge or two to the CEO

Scope creep is a process problem, not a personality problem. Separate what the customer asked for (SOR) from what you committed to (SOW with acceptance criteria and change clauses), sign the SOW together with the contract, and push every modification through a formal change request both PMs sign. Calls don't bind; documents do.

The planned-concession move: when a buyer wants 50 things and 40 are feasible, agree to 10 — then over-deliver to 15 "because we want you to win." Same output, twice the goodwill.

Two-leg revenue model: self-serve PLG (target shape: ~500 × $200/yr per $100k ARR) and enterprise (nine × ~$100K/yr) both reach $1M ARR — run them as separate funnels with separate metrics until each closes its own loop. Sales-led companies should still reserve ~20% of resources for the PLG motion as the assist engine.

Full version: https://clawhub.ai/gingiris-1031/skills/gingiris-b2b-growth
All skills: https://clawhub.ai/gingiris-1031
Follow: @WeiYipei on X

🔗 About the Author

Iris Wei — Growth consultant for 150+ AI startups. Ex-COO at AFFiNE (69K GitHub stars).

🐦 Twitter: @WeiYipei — Daily growth tactics
💬 Consulting: @Iris_carrot on Telegram
🛒 Premium Bundle (all 5 playbooks + templates): Get on Gumroad ($249)
📚 40+ Free Playbooks: gingiris.tools/skills

1	---
2	name: plg-playbook
3	description: \|
4	The complete Product-Led Growth playbook covering freemium model design, self-serve onboarding, activation metrics, and the transition from individual users to enterprise accounts. Follow @WeiYipei on X for PLG insights.
5	source: https://github.com/Gingiris-1031/gingiris-skills/tree/main/skills/plg-playbook
6	tags:
7	- plg
8	- product-led-growth
9	- freemium
10	- free-trial
11	- saas
12	- activation
13	- onboarding
14	- revenue-expansion
15	- b2b-saas
16	- claude-code
17	- ai-agent-skill
18	- agent-skill
19	- latest
20	---
21
22	## 📦 Install
23
24	```bash
25	clawhub install plg-playbook
26	```
27
28	What you get after installing:
29	- Freemium model design — what to gate, what to give away, and pricing psychology
30	- Self-serve onboarding optimization with activation milestones
31	- Enterprise upsell playbook — when and how to layer sales onto a PLG motion
32
33	---
34
35	# Product-Led Growth Playbook — Freemium to Enterprise Conversion
36
37	> 🌍 Language / 语言: [中文](#中文版) \| [English](references/en/README.md) \| [日本語](references/ja/README.md) \| [한국어](references/ko/README.md)
38
39	Let your product do the selling. This playbook covers the full PLG motion.
40
41	- Freemium design: What to gate, what to give away, and pricing psychology
42	- Self-serve onboarding: Time-to-value optimization and activation milestones
43	- Viral mechanics: Built-in sharing, collaboration hooks, and network effects
44	- Usage-based signals: Identifying expansion-ready accounts automatically
45	- Enterprise upsell: When and how to layer sales onto a PLG motion
46
47	## PLG signal gate (2026 field update)
48
49	Free DAU is not proof of PLG. Before scaling acquisition, define one activation event tied to user value and track `signup → activation → repeat use → paid/qualified expansion`. Separate internal/test users and report cohort dates. Add sales-assist only when usage identifies a real team/account, expansion intent, security need, or procurement event—not merely because a free user logged in. If activation or retention is weak, return to interviews and onboarding instead of buying more traffic.
50
51	## When PLG Meets the Enterprise Contract (2026 addendum)
52
53	The PLG-to-sales handoff dies in contract mechanics more often than in product gaps. Field rules:
54
55	Gate custom deployment behind seats. Set a minimum seat count before private deployment is even on the menu. Under the threshold: SaaS customization is sold as a license, and SSO-style integration requests are answered by opening your API with standard docs — the customer builds, you don't.
56
57	Only two asks genuinely require on-prem: regulated data privacy, and integration with an internal permission system. Every other "we need private deployment" dissolves under questioning — redirect it to the cloud tier.
58
59	If you do sign a deployment deal:
60	- Tranche the cash 3:4:3 or 4:4:2 across go-live milestones, with 30% collected at signing
61	- Contractual late fee: 0.5% per day overdue
62	- Keep 1–2 capabilities served from your own infrastructure until the balance clears (agreed upfront, written into terms)
63	- Route stalled payments upward — most senior contact first, then a nudge or two to the CEO
64
65	Scope creep is a process problem, not a personality problem. Separate what the customer asked for (SOR) from what you committed to (SOW with acceptance criteria and change clauses), sign the SOW together with the contract, and push every modification through a formal change request both PMs sign. Calls don't bind; documents do.
66
67	The planned-concession move: when a buyer wants 50 things and 40 are feasible, agree to 10 — then over-deliver to 15 "because we want you to win." Same output, twice the goodwill.
68
69	Two-leg revenue model: self-serve PLG (target shape: ~500 × $200/yr per $100k ARR) and enterprise (nine × ~$100K/yr) both reach $1M ARR — run them as separate funnels with separate metrics until each closes its own loop. Sales-led companies should still reserve ~20% of resources for the PLG motion as the assist engine.
70
71	## Related Gingiris Skills
72	- Full version: https://clawhub.ai/gingiris-1031/skills/gingiris-b2b-growth
73	- All skills: https://clawhub.ai/gingiris-1031
74	- Follow: [@WeiYipei on X](https://x.com/WeiYipei)
75
76
77	---
78
79	## 🔗 About the Author
80
81	Iris Wei — Growth consultant for 150+ AI startups. Ex-COO at AFFiNE (69K GitHub stars).
82
83	- 🐦 Twitter: [@WeiYipei](https://twitter.com/WeiYipei) — Daily growth tactics
84	- 💬 Consulting: [@Iris_carrot on Telegram](https://t.me/Iris_carrot)
85	- 🛒 Premium Bundle (all 5 playbooks + templates): [Get on Gumroad ($249)](https://gingiris.gumroad.com/l/gingiris-complete-global-launch-bundle)
86	- 📚 40+ Free Playbooks: [gingiris.tools/skills](https://gingiris.tools/skills/)
87