Welcome folks! 👋

This edition of The Product-Led Geek will take 8 minutes to read and you’ll learn:

• What is monetisation awareness, and why does it matter so much for conversion and expansion revenue?

• The two most impactful ways to leverage monetisation awareness

• Common pitfalls and best practices for building monetisation awareness into your product experience

Let’s go!

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GEEK LINKS

3 things to check out this week:

• How to Design an Org for Founder Mode

• Navigating Career Decisions in the AI Age

• Vercel’s Guillermo Rauch on What Comes After Coding

GEEK OUT

The Billion Dollar Problem: Your Users Don't Know What You're Selling

Imagine discovering that 70% of your users are unaware of what your paid plans offer.

That's exactly what happened to Elena Verna at SurveyMonkey.

A multi-million dollar revenue leak, hidden in plain sight.

And the inconvenient truth?

SurveyMonkey isn't unique.

We're talking about billions in wasted engineering effort and lost revenue in B2B software.

Most of your users aren’t aware of what you’re selling.

They’re missing out on premium benefits, and you’re missing out on conversion and expansion revenue.

Your engineering team is building features that most users will never discover.

Your existing customers are churning without ever knowing about the solutions you built for their problems.

All due to a monetisation awareness gap.

In this post, I’ll guide you on leveraging monetisation awareness to drive revenue.

Because continuously building new paid features has an opportunity cost, feature work should be balanced with ensuring users and teams know about the extras your paid plans offer.

Even with excellent product–market fit, your conversion engine will underperform if customers don’t know the premium value ahead.

What Is Monetisation Awareness?

Monetisation awareness is a measure of how well your users and customers understand how your paid offerings can help them achieve their goals.

With Product-Led Growth and Product-Led Sales, your product plays a key role in communicating the extra value of your premium features.

In freemium products, converting free users to paying customers hinges on product value and user understanding of the upgrade benefits.

When users remain unaware, your conversion metrics will suffer.

Even with high retention among free users, if most of your user base isn’t informed about the premium offerings, your bottom line will be left on the table.

To make this concrete, here's a quick self-assessment for your product:

• What % of your users can name your top 3 premium features?

• How many touchpoints expose users to premium features in their first week?

• What's your current upgrade rate when users hit usage limits?

If you don't know these numbers, you likely have a monetisation awareness gap.

The Two Primary Types of Monetisation Awareness

Two primary levers can drive significant revenue impact by boosting monetisation awareness:

Intra Use Case Awareness

Intra use case awareness is about helping users understand additional monetised ways you can support them within the use cases they’re engaging with in your product.

In other words, it’s increasing awareness of premium features or limits that amplify or deepen functionality within a single use case.

For instance, when a communication app nudges users by contrasting the free plan’s message limitations with the promise of unlimited messaging in the paid tier, it is creating intra use case monetisation awareness.

Other examples include:

• A collaboration tool highlighting that while free users have access to basic templates or boards, premium options offer a broader library of advanced templates that boost productivity.

• A work tracking tool sharing a team size limitation, beyond which a paid plan is needed.

• An analytics platform showing that free users can create a limited number of reports, while upgraded accounts unlock additional reports and advanced filtering and segmentation options for richer insights.

• A survey platform emphasising that a premium plan provides advanced survey analytics and custom reporting - benefits reflected in the free version only in a limited form.

These are concrete tactics within a user’s current activity - focusing on the extra value within a single use case, and inviting them to upgrade for a better, higher-impact experience.

Here’s Jira highlighting the advanced planning capabilities of Jira Premium:

Richer functionality and additional value, but still within the planning / work orchestration use case.

Any time you see a banner, email, or notification nudging you when you’re near or surpass your free usage limits, that’s intra use case monetisation awareness at play.

In many freemium models, a user’s journey is defined by usage quotas or limits.

A tool might allow users to send a set number of messages per month; as they approach this limit, a well-crafted notification can prompt them to consider upgrading.

The aim is to highlight user pain points at the moment they’re most likely to feel the pinch, prompting them to upgrade to continue using the product without interruption.

Similarly, just showing current usage / consumption leans on this same principle:

Making users aware of limits and sparking curiosity about alleviating them is all part of intra use case monetisation awareness.

Inter Use Case Awareness

In contrast, inter use case monetisation awareness focuses on exposing users to additional premium features that address different, often adjacent or complementary use cases beyond the initial one.

The goal is to broaden the user’s understanding of how your product can deliver value.

For example, a tool might initially attract users with one core functionality (basic messaging) but then promote additional, monetised capabilities (such as custom integrations, advanced analytics, or enterprise-grade security) for divergent use cases.

Similarly in multi-product platforms or suites, navigation items can serve as an ever-present reminder inviting users to learn about additional products and use cases they can adopt.

This broader approach helps drive expansion revenue by encouraging current users to take on more of your product ecosystem as they recognise benefits in unexplored areas.

Monetisation Awareness Quick Reference Table

Why Monetisation Awareness Matters

Ensuring that users understand what you’re selling is crucial for all subsequent revenue growth.

Here’s why it’s important:

• It’s often the root cause of poor conversion. Many monetisation issues aren’t due to a lack of premium value but poor awareness; users simply don’t know the extra benefits available to them.

• It’s more actionable than building new features. Instead of burning resources on additional development, focusing on making existing premium offerings more visible can provide an immediate uplift in conversion rates.

• It amplifies the effectiveness of all growth efforts. When every touchpoint - from onboarding to in-app messaging - reinforces awareness of premium capabilities, a virtuous cycle benefits both customer acquisition and expansion.

• It supports product-led sales initiatives. Clear premium value signals feed into the sales process. Teams can use these indicators as part of their data-driven approach to engage and convert prospects.

Best Practices

The challenge is to ensure your product naturally communicates premium value without overwhelming users.

Here are several best practices:

Consistent Visual Language

Develop a cohesive visual system for premium features and stick to it across all product surfaces.

Use the Rule of Three

Psychological research and advertising theory suggest people need to see a message three times to remember it.

Ensure premium features show up at least three times in the customer journey - in dashboards, tooltips, or email nudges - so users develop lasting awareness of upgrade options.

Contextual Relevance

The timing of your messaging matters.

Tailor your prompts for when they are most helpful: for example, “You’re close to reaching your free messaging limit; upgrading now will remove this cap and allow you to keep sending messages”

By linking the message to a direct, contextual need, you bridge the gap between awareness and actionable intent.

Clear Value Proposition

Marking something with a lock isn’t enough on its own.

Clearly articulate why the premium feature matters - whether it saves time, increases efficiency, or enhances collaboration.

Explain the “what” and “why” of each feature so users understand the upgrade benefit.

You can also lean into the loss aversion principle here (“add credits now or you won’t be able to send more messages”) but don’t overdo it - balance it with a benefit-first approach.

Progressive Exposure

Avoid overwhelming users with all premium features at once.

Start with the essential benefits early, then introduce additional premium features as engagement deepens.

This stepwise approach prevents overload and builds anticipation, leading to a more natural conversion process.

Effective Messaging Examples

Common Pitfalls to Avoid

As you enhance monetisation awareness, be mindful of these traps:

• Information Overload: Resist the urge to push every paid feature simultaneously. Focus on the top-tier benefits that will drive the conversion.

• Poor Timing: Don’t interrupt user workflows with untimely prompts. Instead, deliver notifications at relevant moments—such as when a limit is reached or a contextually important action is attempted.

• Unclear Messaging: Avoid ambiguous cues. If users can’t tell what’s premium and why it matters, the prompt will fall flat. Your messaging must be crystal clear.

• Inconsistent Patterns: Mixed signals confuse users. Stick to a standardised design and messaging structure across all product touchpoints to build trust.

• Missing Measurement: Without tracking your efforts, you won’t know if your strategy is working. Incorporate metrics to gauge awareness, conversion, and engagement to refine your approach.

Measuring Impact

To assess whether your monetisation awareness initiatives are creating positive impact, focus on the following signals:

1. Awareness Rate

Periodically survey your free users to determine what percentage can accurately identify premium features.

Use analytics to track user interactions with your feature walls and upgrade prompts.

2. Conversion Impact

Segment conversion rates by offer engagement level.

Measure time-to-conversion from when a premium prompt is seen, and analyse offer-specific conversion rate differences.

3. Engagement Signals

Monitor interactions indicating premium discovery (e.g., clicks on feature highlights, engagement with usage-limit notifications).

These metrics will serve as early indicators of whether your messaging is resonating.

4. Qualitative Feedback

Use direct user feedback to supplement quant data.

Ask users in surveys or interviews how clear they found the premium messaging and whether they understand the benefits of upgrading.

This insight is invaluable for iterative improvement.

Making it a Win-Win

Think of your premium offers as untapped potential for your users and for your bottom line.

They represent solutions to key user challenges and a significant revenue opportunity for you.

But if users aren't aware of these features, that potential remains locked.

Monetisation awareness is the unlock.

It's an obvious (but usually overlooked) action to clearly demonstrate the different ways in which your product(s) can help the user, their team, and their company succeed.

By highlighting these ways through clear, compelling messaging, you're guiding users to success and simultaneously driving conversion, expansion revenue, and a healthier, more sustainable business.

When they succeed, you succeed.

Win-Win.

Email your experiences with monetisation awareness - both wins and lessons learned - to [email protected] or drop a comment below.

THAT’S A WRAP

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That’s all for today,

If there are any product, growth or leadership topics that you’d like me to write about, just hit reply to this email or leave a comment and let me know!

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Until next time!

— Ben

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