If you're a founder dealing with deal scoring, start here.
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: simplicity beats complexity every time. It sounds simple. It's incredibly hard to execute.
What I've Learned From 36 Companies
A few patterns in deal scoring come up again and again.
The founders who handle deal scoring well understand that simplicity beats complexity every time.
The Numbers Don't Lie
The gap between companies that take deal scoring seriously and those that don't is usually clear.
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, outbound AI, revenue intelligence that I've been thinking about a lot lately.
What's Next
Best practice in deal scoring is changing fast. What worked last year might not work next year. That's both the challenge and the opportunity.
My advice: stay curious, stay humble, and stay close to the people who are actually doing the work. Read less thought leadership and do more experiments. Talk to fewer consultants and more practitioners.
If you're building in this space, the best time to get deal scoring right is before you need to. Don't wait for a crisis to force your hand.
I'll keep sharing what I learn. This stuff matters too much to keep to myself.
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.