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Surviving the Enshittification of Productivity
How to Experiment with AI Without Breaking Your Strategy

What’s “Enshittification,” and Why Does It Matter for marketers and professionals?
In 2023, tech writer Cory Doctorow gave us the word of the year for 2024: “Enshittification.” It’s his beautifully snarky way of describing how platforms and tools start great, then slowly degrade:
At first, they’re user-focused. Everything feels magical.
Next, they prioritize profits. Ads show up; features get locked behind paywalls.
Finally, they’re optimized for shareholders, and user experience goes straight out the window.
Sound familiar? If you’ve ever been locked into a bloated tool with rising costs and fewer benefits, you’ve felt it firsthand.
Now, add AI into the mix. We’re in the middle of a new software boom – over 14,000 tools now exist in the ‘MarTech’ world alone, many powered by AI and built to automate, optimize, or analyze every part of the customer journey. It’s a golden age of experimentation.
But here’s the risk: without a little structure, the explosion of tools can create its own form of enshittification in your operations: disconnected tools, overlapping processes, and franken-stacks that slow you down instead of helping you move faster.
The good news? You can innovate with AI-powered tools, experiment freely, and stay grounded in a successful strategy.
How Martech’s AI Boom Risks Accelerating Enshittification
Buckle up if you think 14,000 tools in the MarTech landscape sounds overwhelming. Between 2023 and 2024, the number of tools ballooned by nearly 28%, fueled primarily by the AI boom. Indie tools, challenger platforms, and major incumbents are all throwing AI-powered solutions into the mix(martech-for-2025-report).
At first glance, this explosion seems great—more tools, more options, more ways to solve your problems. But here’s the catch:
Franken-Stacks Are Real: With tools proliferating, companies risk cobbling together disconnected systems that overlap in features and clash in workflows.
Shiny Object Syndrome: A new tool promises “instant ROI” or “automagic optimization,” and teams jump in without asking why. The result? Bloated stacks that slow teams down instead of speeding them up.
AI Tools Are Still Maturing: Many tools are hyper-specialized (e.g., content generation, lead scoring, or data scraping) but incomplete on their own. You integrate 10 tools to solve one problem—inefficient, janky, and costly.
The report highlights how marketers today are already testing AI-driven tools in over 50+ use cases, from content ideation (69%) to chatting with data (39%)(martech-for-2025-report). But without governance, this tool overload threatens to backfire.
Building Smarter Systems to Avoid the Pitfalls
To survive this gold rush moment without falling into chaos:
Audit Your Tech Stack Regularly: Ask yourself, “Do these tools solve unique problems, or are we duplicating effort?” AI adoption is accelerating, but smart marketers are treating it as an evolution, not a free-for-all.
Embrace Composability: API-first tools and open ecosystems allow you to connect systems seamlessly. It’s the antidote to siloed tools and Franken-stacks(martech-for-2025-report).
Stay Sandbox-Centric: Follow the “hack, pack, stack” progression: experiment quickly (hack), validate solutions properly (pack), and integrate proven tools into your strategy (stack)(martech-for-2025-report).
The Martech landscape isn’t shrinking anytime soon, but your approach can be smarter: leverage tools thoughtfully, integrate strategically, and prioritize ROI over novelty.
Final Thoughts: Innovate, Don’t Implode
Software and AI are in a gold rush moment – and that’s exciting. Tools empower marketers to build workflows, automate tasks, and experiment like never before. But experimentation doesn’t have to mean chaos.
Keep your core strategy strong, play in a controlled sandbox, audit regularly, and, most importantly, ask why before you try.
Innovation isn’t about adding more tools—it’s about building smarter systems. Follow that path and keep enshittification out of your marketing stack.
This Edition’s Laugh
Simple Checklist to Prevent Enshittification
Before Testing a Tool:
Does it solve a real problem?
Will it integrate with our stack?
Do we know how to measure success?
Quarterly Audit:
Is the tool still used?
Does it drive value?
Is there overlap with other tools?
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As Seen on Product Hunt: Knowledge Base Tools 🧠
If you’re drowning in scattered docs or answering the same questions on repeat, it’s time to level up your knowledge management game. These tools streamline documentation, FAQs, and team resources so you can save time, reduce chaos, and make finding answers actually easy. Neat, right?
Mintlify – Modern, sleek documentation that’s user-friendly and beautiful. → Product Hunt
Docusaurus – Open-source docs made simple—Markdown-powered and customizable. → Product Hunt
Whimsical – Align your team with clear, collaborative product docs. → Product Hunt
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Cool cool, now go tame that doc jungle. 🌿
One Shot ChatGPT Jokes:
So I ran this super janky B2B marketing campaign last quarter. Turns out, it went viral—but mostly because everyone was forwarding it around like, 'Can you believe these people actually hit send on that?!' I guess I found a new audience: folks who appreciate cringe as a lifestyle choice. 🙃
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