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Each of us has – at one point or another – fallen madly, deeply in love with an app.

Some inefficiency in your life, some void filled by an app that seems almost perfectly tailored to you.

You wonder how you survived before the app existed. You move the app to that prime real estate in your main menu bar. You consider naming your firstborn child after it.

Then, one day, at the height of your immersion in the tool, right when you’ve so integrated it into your life that you can’t imagine what you’d do without it, tragedy strikes.

You’re prompted to upgrade.

You’ve reached the freemium limit and all of a sudden, you’re at a crossroads. To upgrade or not upgrade? That is the question.

While it may sting a bit to bust out your card and sign up for a subscription, give credit where credit’s due: companies successfully adopting the freemium model nowadays know just the point of critical mass for their users.

They know just the features to withhold and just the time to prompt you.

And here’s the thing: that’s really hard to do right.

A good freemium product needs to strike a balance between offering just enough features to make you fall in love, but not so many that you’re able to operate without the upgrade.

We’ve put together upgrade prompts from top apps and sites like LinkedIn, Trello and Canva to examine what goes into creating the perfect freemium upgrade prompt.

Trello Limits Your Integrations

Atlassian’s most recent acquisition, Trello, utilizes the freemium model to convert individual users of the project management platform to business class or enterprise solutions.

Like Slack, Trello leverages open source integrations to create harmony amongst the tools its users need on a daily basis. Integrations include Dropbox, Evernote, and MailChimp – three other notable freemium services.

These integrations can be the difference between using Trello as a standalone project management tool and fully integrating into the way you stay organized across all tools.

Trello wants to give you a taste of that, but not the whole cake.

Users are allowed one free integration and can scan the entire library of the 100+ offerings.

Anyone who enjoys synergy among apps will have their mind spinning as they think of the possibilities of syncing with Harvest or Google Drive, but when you go to enable that second integration, you’re prompted with the following:

Trello does a few things really intelligently here:

  1. You can try each integration individually.

Switching out integrations is as simple as clicking the “Enable/Disable” button – no “one and done” policy here.

Smart move for Trello because users can test the integrations individually.

That means when they realize how great it would be to use both join.me and Salesforce, that upgrade prompt will look a lot more enticing.

  1. They empathize with their users.

The opening line of the upgrade prompt reads like they’re a close friend who doesn’t want you to have to upgrade either.

“If only there weren’t these darn paywalls that we built!”

In all seriousness, empathizing with your users about upgrades is a smart move.

It shows you’re on their side and are glad they’re finding value in the platform.

Spotify does this well also, and 25% of their active users pay for premium accounts (which is an insane number).

  1. They remind of the free capabilities but lead to the paid solution.

Sure, you could just write “You can’t do that!” and then provide a CTA, but you’d be walking a tight rope between upgrading and frustration.

Instead, a slight nudge that reminds users what they can do for free (but alludes to the benefits of upgrading) keeps users happy within the limitations of your model.

In short, a good freemium upgrade is self-aware enough to understand the biggest value add for their users, and then smart enough to give them a preview

Feedly Celebrates You

Feedly is an RSS feed aggregator with both free and “Pro” accounts.

Users of the free platform get 100 feeds with minimal organizational tools while pro users get:

  • Unlimited feeds
  • Unlimited organization
  • Alert tools
  • Integrations
  • Data backup
  • Premium customer support

So, as you can see, pro users benefit from a mix of product and service upgrades that for heavy-duty RSS feed fans, may be worth the $5.41 per month.

The more interesting part of Feedly’s freemium model isn’t the difference in features, but rather when and how they prompt users to upgrade.

Feedly positions their upgrade as a “gift” being offered as a thank you for your patronage once you hit two months of use.

A 30 % discount is offered on a limited time basis (“today only”).

It’s a pretty crafty strategy for encouraging upgrades.

First, because the prompt reminds users that they’ve been active on the platform for some time now.

Second, because in conjunction with that reminder, users have an opportunity to now upgrade at a significant discount for the year.

Finally, because that discount is timestamped, forcing users to give a thought – then and there – on whether or not an upgrade makes sense.

LinkedIn Recognizes Commercial Activity

Everyone knows LinkedIn as a go-to source for professional networking, job search, and industry content, but with 467 million members sharing their work experience on the platform, it’s also a go-to source for recruiters to find talent.

In fact, some numbers show as many as 94% of recruiters use LinkedIn in some form in their business.

The staffing industry alone is worth $142 billion – not to mention internal corporate recruiting – so needless to say, LinkedIn has long been positioned to profit from some members’ commercial use of the platform.

And to be clear, they have been doing just that since 2008 when LinkedIn Recruiter – a premium platform built specifically for, you guessed it, recruiters – launched.

LinkedIn has several tiers to its premium subscriptions based on how you intend to leverage their network. But, like most tools using a freemium model, users tend to max out their use of the free platform before deciding whether or not to upgrade.

LinkedIn’s strategy to capture potential upgrade-eligible users shows up right in the middle of a recruiter’s workflow in the form of a soft paywall:


The policy of how members reach this commercial use limit are detailed in LinkedIn’s help center, but in short: if you’re someone whose business runs on finding people through LinkedIn, the amount of work you’re able to do for free on the platform is fairly limited.

By stopping commercial users of the platform literally mid-search, LinkedIn quickly demonstrates the limitations of the free version while also positioning the upgrade as a recruiter’s salvation: premium solutions have unlimited searches.

LinkedIn also combines their freemium model with the more traditional “30-day free trial,” giving users the opportunity to test drive the difference in a premium account before fully committing to an annual contract.

The end result is positioning an upgraded platform for those who use LinkedIn to build their own businesses and profit.

Canva Taps Users with Helpful Upgrade Features

Need a quick, professional, beautiful graphic in a pinch? Canva may be just the tool for you.

Canva positions themselves as “amazingly simple graphic design software” and in my limited use of the platform, I can confirm that’s actually true.

Users create an account and can quickly toggle to different templates based on what you’re looking to create: a social media post, blog graphic or even a poster.

For someone keeping an eye out for upgrade prompts, it doesn’t take long to recognize how Canva leverages the freemium model.

Yes, you can use templates, make simple changes and even download your work for free on Canva, but when you start to extend into features that would really allow Canva to replace Photoshop and become your go-to graphic design resource, subtle nudges toward the premium solution arise.

Canva details all the feature differences on their pricing page, but essentially the free version of Canva works great for an individual who needs a one-off design done well.

For serious graphic designers, these subtle nudges will eventually drive you and your team toward the upgrade check-out.


Adopting a freemium model for your product or service gives users an opportunity to dive into your platform headfirst, immerse themselves in what you offer and then decide whether your offering is so critical that they’re willing to transition from a free user to a paying one.

The difficulty comes in first deciding what’s offered for free and what’s protected behind the premium solution.

It’s tough striking the balance between just enough features to drive adoption, but not so many that an upgrade feels unnecessary.

The second difficulty comes in deciding the best way to prompt your users to upgrade.

Whether it’s Trello relating to customer’s desires for synergy, Feedly gifting discounts, LinkedIn limiting commercial activity or Canva subtly revealing the full capabilities of their platform, companies have implemented different methods for converting freemium users with varying degrees of success.

As more and more companies adopt freemium models, I’m sure we’ll see companies getting more creative with upgrade prompts.

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