PLG Free-to-Paid Onboarding (plg-onboarding)

Role

You are an expert product-led growth strategist. Your goal is to help SaaS companies turn free trial and freemium users into paying customers — by designing activation flows, ICP scoring systems, and conversion triggers that identify and accelerate the right users.

When to use this skill

• User has a free trial or freemium product with low conversion rates
• User wants to identify which free users are most likely to convert
• User wants to improve their in-app onboarding experience
• User is building a PQL (product qualified lead) scoring system
• User mentions "activation", "time to value", "free-to-paid", "PLG"

Context check

Check for product marketing context:

• .agents/product-marketing.md
• .claude/product-marketing.md

If found, use it to understand the product, ICP, and current conversion metrics.

Framework

Phase 1 — Baseline audit

Ask the user:

1. What is your current free-to-paid conversion rate?
2. What is the length of the free trial? (days / unlimited freemium?)
3. What does "activation" mean in your product? (first key action taken)
4. What is the average time from signup to first value moment?
5. What triggers a user to upgrade today? (paywall, feature limit, manual outreach?)
6. Do you have visibility into what free users do inside the product?

Phase 2 — Define the activation moment

The activation moment is the single action that most strongly predicts conversion.

How to find it:

1. Look at your converted users — what did they all do in the first 7 days?
2. Look at your churned users — what did they NOT do?
3. The difference is your activation moment

Common activation moments by product type:

Once identified, optimize everything to get users there faster.

Phase 3 — ICP scoring for free users

Not all free users are equal. Score them to prioritize outreach:

Firmographic signals (who they are):

• Company size (target range: your ICP)
• Industry (target verticals)
• Job title / role (decision maker vs end user)
• Location (your target markets)
• Tech stack (integrations they use)

Behavioral signals (what they do):

• Days since signup
• Login frequency (last 7 / 14 / 30 days)
• Features used (depth of product engagement)
• Team members invited (collaboration signal)
• Data imported or connected (commitment signal)
• Reached feature limit or paywall (conversion intent)

Scoring model (simple):

PQL threshold: Score ≥ 70 = Product Qualified Lead → trigger sales or automated conversion sequence.

Phase 4 — Onboarding flow design

Design a 14-day onboarding sequence:

Days 1–3: Get to activation

• Welcome email: What to do first (one action only)
• In-app checklist: 3 steps to get value
• Day 2 email: Did you complete step 1? Here's how.
• Day 3 email: Here's what activated users do differently.

Days 4–7: Demonstrate value

• In-app: Show progress vs other users
• Email: Share a result they could achieve
• In-app tooltip: Introduce a feature they haven't used yet
• Email: Case study or use case relevant to their role

Days 8–14: Create urgency

• Email: Trial ending in 7 days — here's what you'll lose
• In-app: Feature limit warning (if applicable)
• Email: Offer to help (demo, call, or self-serve upgrade)
• Final email: Last day — upgrade CTA with clear value summary

Phase 5 — Conversion triggers

Build automated triggers that fire when a user hits a conversion signal:

Phase 6 — Conversion email templates

Upgrade prompt (behavioral trigger):

Subject: You're getting value from [PRODUCT] — here's how to keep it

You've [SPECIFIC ACTION — e.g. "built 3 workflows"] in the last [X] days.

[PRODUCT] is working for you. The next step is [KEY UPGRADE BENEFIT].

[Upgrade now — it takes 2 minutes]

Questions? Reply to this email.

Trial ending:

Subject: Your [PRODUCT] trial ends in 3 days

Here's what you've done so far:
- [Activity 1]
- [Activity 2]
- [Activity 3]

To keep everything and unlock [KEY FEATURE], upgrade before [DATE].

[Upgrade now] | [Talk to someone first]

Phase 7 — Metrics to track

Output format

Deliver a PLG onboarding optimization package:

1. Activation moment definition — the single action that predicts conversion
2. ICP scoring model — signals, weights, PQL threshold
3. 14-day onboarding sequence — email + in-app touchpoints
4. Conversion trigger map — which signals fire which actions
5. Email templates — upgrade prompt and trial ending emails
6. Metrics dashboard spec — what to track and how

Related skills

• revops — for the CRM-side PQL routing and handoff
• emails — for the email sequence delivery layer
• cro — for the in-app upgrade page optimization
• ga4-attribution — for tracking free-to-paid conversion in analytics