Grammarly Monetization Case Study: How "Premium Feature Sampling" Doubled Conversions

When Albert Cheng became VP of Growth at Grammarly, 90% of users were on the free plan and ignoring every upgrade prompt to the paid version.

The product wasn't the problem. Premium could rewrite clunky sentences, fix tone issues, and expand vocabulary. But free users never saw these features, so they treated Grammarly as a basic spellchecker. Paying for better spellchecking didn't make sense.

Invisible value doesn't convert.

Grammarly's invisible value problem

The free product fixed spelling. The paid product fixed writing.

Because the advanced features were completely hidden behind a paywall, users built a mental model that "Grammarly equals spellcheck." Most ignored upgrades because paying a monthly subscription just to fix "their" vs "there" felt unnecessary.

This is the standard freemium failure mode. You gate your best features to create pressure, but gating often creates ignorance.

Interspersing paid suggestions in free workflows

Albert's team tried something different. They interspersed premium suggestions directly inside the free experience. When users typed, Grammarly would flag harsh tone or repetitive words. Users could see the suggestion and read the improvement, but couldn't apply it with one click.

That's the difference between a paywall and a window.

Users experienced the value of an actual editor before paying a cent. They saw the gap between decent writing and polished writing.

Premium feature sampling creates information symmetry

This is the Costco sample strategy applied to software. You taste the white cheddar before buying the block. The sample proves quality and removes risk.

Before this experiment, upgrading to Grammarly Premium was a gamble. Users had to trust marketing copy. By showing paid suggestions, they removed the gamble. Users saw exactly what they were missing.

The decision shifted. It wasn't about trusting an ad anymore. It was about wanting that specific fix.

Upgrades nearly doubled

The impact was immediate. Albert confirmed that upgrade rates nearly doubled. It became the single biggest monetization win during his tenure.

Users didn't feel tricked. They felt informed.

The "freeloaders" weren't cheap. They were just under-educated about the product's capabilities. Once they saw the utility, they pulled out their credit cards.

Applying the sampling strategy to your SaaS

Most PLG companies hide their best work. They assume users will upgrade to "unlock power." But users can't crave power they haven't tasted.

Show the output. Gate the execution.

If your tool helps sales teams find prospects like Apollo, show the exact CEOs the user wants to pitch. Blur their phone number.

If your platform runs on professional curiosity like LinkedIn, tell the user "5 recruiters at Google viewed your profile." Blur their names.

If your tool analyzes search traffic like Ahrefs, show the high-volume keyword list. Blur the difficulty metric or disable the export button.

Let the product sell itself. Marketing can promise value, but only the product can prove it.

Source: Albert Cheng

Top Tweets of the day

1/

Good example of using TikTok for local targeting.

2/

Love this tactic. Target AI SEO phrases using Google Search Console.

3/

Such products will absolutely print on short-form platforms like TikTok & Instagram since more kids are born every year. And kids love talking to AI like ChatGPT, but soft toys make this even better.

The genius is the models are absolutely better at talking now. Microsoft has released VibeVoice ASR which is super duper fast and I love listening to Grok's voice for reading long-form articles. Its a seductive female voice made for gooning but very good on ears. I divide articles into chunks of 1000-words to read long-form 5000 word articles as I tend to procrastinate long-form reading due to fucked up attention span. Read a pretty badass article today in ~20-30 minutes. ChatGPT voice is good too but Grok’s much better. You can even voice-clone using your favorite voice like Scarlett Johansson’s voice & then recreate voice clone using Kokoro TTS.

If you are into e-comm, this (or OpenClaw Raspberry Pi) is the product to sell. I always thought talking to an AI voice is gooning but there are other use cases where it is extremely better to listen so you can focus. Like long-form reading for me. Try it if you haven’t.

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