Rolling out deal scoring at scale is where most plans break.
When I first tried scaling our sales team, I failed miserably. It wasn't until we implemented deal scoring that everything clicked. Here's the exact framework we used to 3x our pipeline without adding headcount.
The Counterintuitive Truth
In deal scoring, the best practitioners often do less, not more.
The lesson: you should focus on one thing and do it exceptionally well. It sounds simple. It's incredibly hard to execute.
The Framework That Actually Works
Here is a simple framework for evaluating deal scoring. It's not complicated, but it requires discipline.
Step 1: you should focus on one thing and do it exceptionally well
This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: the market doesn't care about your roadmap
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 deal scoring right treat it as an ongoing process, not a one-time project.
What I've Learned From 122 Companies
A few patterns in deal scoring come up again and again.
The founders who handle deal scoring well understand that the best solutions are often the simplest ones.
The Numbers Don't Lie
Investing early in deal scoring can be the difference between raising your next round and running out of runway.
One of my portfolio companies went from struggling to profitable in under a year after they finally got serious about this. The founder told me later that they wished they'd started sooner.
This connects to broader themes around AI sales tools, sales forecasting AI, conversational sales AI, deal scoring AI that I've been thinking about a lot lately.
The Bottom Line
None of this is rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at deal scoring aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
Companies that take deal scoring seriously tend to pull ahead of the ones that don't.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
Frequently Asked Questions
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.
Q:How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.
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.