Paywalls PLG: 3 steps to get Customers to upsell

Paywalling isn't just about blocking features—it's an art of creating value, driving discovery, and nurturing customer relationships.

Heres are the 3 steps I used to convert 50 free PLG customers into paying customer:

1️⃣ Understanding Paywall Philosophy 🧱💲

The journey begins with thoughtful feature gating. Here's our strategic framework:

Key Considerations:

❶ Analyze user behavior through Monthly Active User (MAU) metrics

Find some sort of pattern from whatever data you have (calls, usage)

❷ Identify your unique value proposition

You want your free customers to experience these right away!

❸ Focus on growth mechanics that encourage sharing

You want your free customers to share and create virality!

❹ Resist the temptation to gate everything

Don't be force by the pressure of upsells to gate every feature 🙅‍♀️

❺ Implement strategic usage limits when necessary

If you are forced 😂… add a usage limit cap to the feature

2️⃣ Product Experience: Making Paywalls Discoverable 🕵🏽

Onboarding Insights

During our 30-minute onboarding calls, we don't just introduce the platform—we create a narrative of value. We strategically highlight advanced capabilities like policy addition, control customization, and framework implementation.

In-App Discovery Techniques

We collaborated closely with the design team to develop subtle yet powerful discovery mechanisms. Use strategic star (⭐️) markers for advanced features, implement intelligent in-app onboarding flows, and display usage limit banners that guide without being overwhelming.

3️⃣ Leveraging Customer Success for Paywall Navigation 🙋🏻‍♂️

Educational Reinforcement

Our approach combines automated and high-touch communication strategies:

• Targeted educational emails

• Screenshot-guided feature explanations

• Personalized follow-up conversations

• Pricing tier reminders that highlight potential upgrades

Strategic Bundling

We transform potential friction points into value-added experiences:

• Trigger hand-raiser automations for advanced feature exploration

• Create bundled offerings that provide tangible additional value

• Customize policy and control packages that feel like strategic investments

The Heart of Paywall Strategy 💡

Paywalling isn't about restriction—it's about creating pathways to enhanced value. By making discovery intuitive, educational, and genuinely helpful, we transform potential barriers into exciting opportunities for customer growth.

Pro Tip: Every paywall is a conversation, not a roadblock. Design it with empathy, clarity, and a genuine desire to help your customers succeed.

Remember: The goal isn't just to monetize but to continuously demonstrate the extraordinary value your SaaS provides. Make discovery feel like a journey of potential, not a transaction. 🚀

Post-Sales and Product Led Growth

1. Get those G2 Reviews! 🤩

2. Find more upsells with this post-sales playbook 🤑

3. Understand reasons why customers churn: 5 Churn analysis and methods 😵‍💫

Retention and Product Led Growth

1. How we increased retention by activating +45% of our PLG customers? 📈

2. What is a good vs. great retention benchmark? 📊

3. Who owns retention? 🫵

4. Five ways to improve retention in PLG 🖐️

Roadmaps and Product-led Growth

1. How do I convince Product, Design, and Engineering to build PLG features? 😍

2. How do I know we are building the right things for PLG? And what are the success metrics? 🤔

3. How to use customer feedback in your PLG product roadmap? 🗣️

4. How to communicate product-led growth Roadmap to Stakeholders? 😰

5. How to handle stakeholder requests? 😅

I write daily*** about my learning on launching and leading PLG. Feel free to subscribe.

I am Gary Yau Chan. 3x Head of Growth. Product Growth specialist. 26x hackathon winner. I write about #PLG and #BuildInPublic. Please follow me on LinkedIn, or read about what you can hire me for on my Notion page.