I’m going to say what most EdTech founders are afraid to: your expensive AI grading software is probably useless. After testing dozens of platforms, I found they miss nuance and penalize creativity. Here’s my framework for effective AI-assisted grading that actually works.
The Framework That Actually Works
Here is a simple framework for evaluating AI grading tools. It's not complicated, but it requires discipline.
Step 1: timing is everything in this game
This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: you should focus on one thing and do it exceptionally well
Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly
Nothing works perfectly the first time. The companies that get AI grading tools right treat it as an ongoing process, not a one-time project.
What I've Learned From 99 Companies
A few patterns in AI grading tools come up again and again.
The founders who handle AI grading tools well understand that simplicity beats complexity every time.
The AI Angle
Any discussion of AI grading tools in 2026 has to include AI. As someone who's invested in Anthropic, OpenAI, Scale AI, and Hugging Face, I have a front-row seat to how AI is transforming this space.
The short version: AI makes good practitioners better and bad practitioners worse. It's an amplifier, not a replacement.
Some teams use AI to get far more out of AI grading tools. Others spend heavily on AI that solves the wrong problem. The difference comes down to understanding what you're actually trying to achieve.
This connects to broader themes around ai grading, teaching strategies, contrarian that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But you don't need to get AI grading tools right on day one. You just need to get started and keep improving.
Founders who do well at AI grading tools tend to share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
Q:Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
Q:What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 234 startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
Q:What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.