Turning Users into Customers

The Conversion Trigger Playbook

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Jonathan Anderson
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Bio | Madison Leonard is a seasoned pro in Product-Led Growth (PLG) with a knack for turbocharging high-growth startups (Vanta and ClickUp). As a growth and marketing advisor, she's your go-to guide for growth, whether you're a fresh startup or eyeing an IPO. Madison's all about unleashing new products, creating buzzworthy brand moments, perfecting PLG growth loops, and building top-notch teams.

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Wondering how to convert free users into paying customers? Product growth teams are constantly experimenting with messaging and prompts to boost conversions. But what's in the toolkit of conversion triggers, when to use them, and what practices work best? In this blog post, we'll provide you with a framework for different conversion triggers, complete with real customer examples.

Conversion Triggers for Usage-Based In-App Upgrades

When it comes to in-app upgrades, the conversion journey is a whole different ball game compared to traditional product launches or gated free trials. Let's break it down into distinct stages, each with its own set of triggers.

Ready? Let’s convert. 

1. Awareness

In the realm of usage-based triggers, awareness isn't about flashy marketing campaigns; it's about keeping upgrade options visible within the app. Here are some examples:

Examples of Awareness triggers:

  • Upgrade Buttons: Place upgrade buttons prominently in the app interface.
  • Lock Icons: Use lock icons to indicate locked features, letting users know about available upgrades.

User Emotion: Neutral - it’s neither good or bad, it just exists

When to use: Persistently in the UI 

Customer Example: Imagine an email marketing platform displaying an "Upgrade to Premium" button at the top of the dashboard, ensuring users always know about the premium option.

2. Lure

Lures are time-based triggers designed to spark users' interest in upgrading. They should be tied to specific user actions or milestones. Random pop-ups can harm your brand, especially when they appear liberally, so use lures wisely!

User Emotion: Curious or Urgent

When to use: Strategically and with heavy segmentation

Example Lures include:

  • Flashing Badge: Pique a user’s interest softly (great for new feature or release notes alerts)
  • Top Banner: Utilize a banner at the top of your app to highlight an upgrade chance.
  • Contextual Pop-ups: Introduce pop-ups when users are acutely aware of their usage

Customer Example: Picture a project management tool offering a 30% discount on upgrading once a user has created five projects. A banner appears at the top of the screen, inviting the user to upgrade.

3. Risk Evaluation

When users encounter a lure, they often assess the risks associated with upgrading. Users are naturally cautious and skeptical, so even during a conversion moment, your users will consider potential drawbacks. To address this, provide incentives to reduce perceived risks. 

User Emotion: Cautious or Skeptical

When to Use: Always! Assume that a user will be intrigued yet skeptical with any upgrade lures… proactively counter with risk-free incentives. 

Risk Evaluation triggers can include:

  • Free Trials: Offering free trials to allow users to experience premium features risk-free.
  • Ease of Transition: Providing templates and resources to make the transition to a premium plan seamless.
  • Hand Holding: Offer 24/7 support through chat, email, or phone in addition to self-serve FAQs and help articles. For Enterprises, this could also mean white-glove service as needed. 

Customer Example: In a project management tool, users get a 7-day free trial of the premium plan, along with templates and guides for a seamless transition.

4. The Hook

The hook is that "aha" moment when users recognize the value of the premium offering.  It's the point where users are relieved (you’re solving their problem), inspired (thinking of all the ways your tool could be used), or delighted (with awesome experiences) via the premium features. This varies for each product and user, so tailor your triggers accordingly.

User Emotion: Delighted, Inspired or Relieved

When to use: Immediately after a user has taken action with the new

While every product’s hook is different, there are a few ways to support activation:

  • Ease of Transition: Providing templates and resources to speed up the time-to-value.
  • Inviting Others: Encouraging users to invite colleagues or team members, especially if collaboration is a key activation metric. 

Customer Example: A design tool provides templates and collaboration to help unlock the ‘aha’ moment faster.

5. Push

Providing value for an individual user is easy - but in B2B, you also have to convince managers, colleagues, and/or leadership before you can make the purchase. 

Users need help getting things over the finish line. 

User emotion: Cautious yet curious

When to use: Along the way, but especially after activation 

Push reinforcements can include: 

  • Social Proof: Providing case studies, customer reviews, referrals, and other forms of social proof can give sufficient brand authority for a decision. 
  • Nurture Triggers: Ensure the activation trigger is repeatable over a set duration with further in-app lures and emails to bring them back in the product consistently. 

Customer Example: A whiteboard product might showcase case studies or logos of successful businesses that achieved greater productivity and efficiency through premium features.

6. Decision

This is the moment of truth you’ve been waiting for… their decision. 

User Emotion: Confident (no matter what decision they made)

Customer Example: A chat tool ensuring you upgrade before are able to use an upgrade feature.


Discovering and deploying the right conversion triggers may seem complex, but a well-structured framework simplifies things. Understand the stages of awareness, lure, risk evaluation, the hook, and decision to customize your approach to your product and user base. The key to success is aligning these triggers with your users' needs and expectations, ultimately driving conversions and fueling product growth.

Happy converting.


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