Superhuman's Grammarly Acquisition: The Inevitable Enshitification Playbook

The Superhuman acquisition news dropped while I was halfway through my morning espresso, and I’ve spent the last few hours fielding texts from founders and operators asking for my take. So here it is: we’re about to witness a textbook case of what Cory Doctorow calls “enshitification”—the three-stage death spiral of platform collapse.

The Perfect Acquisition Target

Let’s be clear: Superhuman built a genuinely exceptional product. I’ve been a power user since 2019, paying $30/month without hesitation because it delivered exactly what it promised—a genuinely better email experience. They turned the mundane into something approaching sublime through obsessive attention to detail and product discipline.

It was also, from an operational standpoint, a perfect acquisition target:

• A highly engaged user base willing to pay premium prices
• Remarkable brand loyalty and Net Promoter Score
• A mature, stable product with manageable maintenance costs
• A clear value proposition focused on saving time for high-value knowledge workers
• Proprietary technology and interaction patterns

The price tag (which sources put north of $500M) makes perfect sense given Superhuman’s 100K+ paying subscribers at $30/month. That’s a $36M ARR business with margins that make SaaS investors weep with joy.

From Grammarly’s perspective, this is a strategic masterpiece. From users’ perspective, we’re about to experience the tried-and-true enshitification cycle that’s killed dozens of once-great products.

The Three-Stage Enshitification Death Spiral

If you’re not familiar with Doctorow’s framework, enshitification is the predictable pattern that occurs when platforms prioritize extraction over value creation:

1. The Honeymoon: Platforms start by delivering value to users to attract them
2. The Squeeze: Once users are locked in, the platform begins extracting value
3. The Collapse: Quality degrades until users leave and the platform dies

We’re currently in the final days of Stage 1 for Superhuman users. The next 24 months will be a masterclass in Stage 2.

Why This Acquisition Specifically Signals Enshitification

When I look at this deal structure, three red flags immediately stand out:

1. The Fundamental Business Model Misalignment

Superhuman built its reputation on privacy, speed, and elegant simplicity. Grammarly’s entire business model is predicated on analyzing your writing, feeding that data into AI systems, and increasingly inserting itself between you and your content.

This creates an irreconcilable tension: Superhuman users pay for fewer distractions, while Grammarly’s roadmap necessarily requires more interruptions, more suggestions, and more data collection.

2. The Integration Impossibility Problem

I’ve overseen 9 post-acquisition integrations as a fractional COO. The first question is always: “How do we merge the codebases?” In this case, the answer is: “You don’t.”

Superhuman is built on a highly opinionated, specialized architecture designed for speed above all else. Grammarly’s system is designed for continuous scanning, analysis, and intervention. These are fundamentally incompatible technical approaches.

The only viable path forward is what I call “product cannibalization”—where specific features are extracted and grafted onto the acquirer’s platform while the original product slowly withers.

3. The Culture Collision

Superhuman’s culture was built around an almost pathological obsession with performance and user experience. Their founder Rahul Vohra is famous for his “emotion-centered design” philosophy—optimizing the product to make users feel accomplished and elevated.

Grammarly’s culture, for all its strengths, is optimization-driven. Their north star is accuracy and suggestion quality—how many errors they catch, how many improvements they suggest.

When these cultures collide in product decisions, guess which approach will win? The one that drives immediate revenue and engagement metrics.

The Enshitification Timeline We’re About To Witness

Based on my experience with similar acquisitions, here’s how the next 24 months will play out:

Months 0-3: The Reassurance Phase

• Flowery blog posts promising “nothing will change”
• Founders making media appearances talking about “shared vision”
• Minor UX improvements to demonstrate ongoing investment

Months 4-8: The Integration Phase

• Initial Grammarly features appearing in Superhuman (likely starting with subtle writing suggestions)
• Privacy policy updates that most users will blindly accept
• Backend infrastructure migrations that cause occasional performance issues

Months 9-18: The Monetization Phase

• Price increases disguised as “new feature tiers”
• More aggressive Grammarly integrations
• New onboarding flows designed to cross-sell Grammarly’s full suite
• Increasing latency as more tracking and analysis is added

Months 19+: The Abandonment Phase

• Core team departures
• Maintenance mode with minimal updates
• Eventual announcement of “unifying our products” (translation: killing Superhuman)

The tragic irony is that this enshitification process isn’t driven by malice—it’s driven by completely rational business decisions and the structural realities of how acquisitions work.

The Business Physics Behind Acquisition Enshitification

From my perspective as someone who’s been on both sides of these deals, the degradation of Superhuman isn’t just likely—it’s mathematically inevitable based on three operational realities:

1. Acquisition ROI Mechanics

Grammarly didn’t pay half a billion dollars because they admired Superhuman’s elegant code. They paid because they calculated a specific ROI based on:

• Monetizing Superhuman’s existing user base more effectively
• Cross-selling Grammarly to Superhuman users
• Applying Superhuman’s technology to Grammarly’s much larger user base

None of these core ROI drivers involve “keeping Superhuman exactly as it is.”

2. The Integration Cost Equation

Maintaining two separate products with different codebases, infrastructures, and teams is enormously expensive. The financial pressure to consolidate is relentless, especially when growth inevitably slows.

Every quarter, someone will present slides showing how much money could be saved by merging infrastructure, teams, and eventually products.

3. The Organizational Gravity Problem

In every acquisition, the larger company’s processes, priorities, and politics eventually consume the smaller company. This isn’t because larger companies are evil—it’s because organizational systems are designed to replicate themselves and resist foreign elements.

Grammarly has 800+ employees. Superhuman has around 30. Guess whose processes, priorities, and decision frameworks will dominate?

What This Means For Users (And The Broader Market)

If you’re a Superhuman user, enjoy it while it lasts. The product you love will gradually transform into something else—something more intrusive, more “helpful,” more cluttered, and ultimately less aligned with what made you fall in love with it in the first place.

The broader market implications are more interesting. This acquisition signals that we’ve entered a new phase of productivity tool consolidation, where specialized tools with passionate user bases are being absorbed into larger platforms.

The result is a classic market opening for new, focused entrants. History shows that periods of consolidation and enshitification create fertile ground for the next generation of products that promise—and initially deliver—on the purity of purpose that made their predecessors great.

In fact, I’d bet good money that right now, somewhere in San Francisco, New York, or Bangalore, a small team is building “what Superhuman should have been” with the explicit goal of capturing disillusioned users 18 months from now.

The Rare Exceptions

To be fair, there are rare examples of acquisitions that don’t follow the enshitification pattern. The common elements in these exceptions are:

1. The acquirer has a genuinely long-term perspective and understands the fragility of user trust
2. The acquisition target retains significant operational autonomy
3. The business models are naturally aligned rather than forced together

Unfortunately, the Grammarly-Superhuman deal shows none of these characteristics.

The Ultimate Lesson: System Design Trumps Intentions

The most important takeaway here isn’t about either company—it’s about how system design inevitably trumps intentions.

I’ve sat in rooms with brilliant, well-meaning executives who genuinely wanted to preserve what made acquired products special. But the systems they operate within—financial expectations, integration timelines, organizational politics—create irresistible pressure toward enshitification.

This is why truly great products are rare and fleeting. The very success that makes them valuable acquisition targets also plants the seeds of their eventual degradation.

Superhuman was exceptional. Pour one out for what it was, and start looking for what will replace it.