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 Reality Nobody Talks About
A lot of the advice on deal scoring rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that your team matters more than your technology. I've seen this play out across dozens of companies. The pattern is unmistakable.
Many teams spend months on the wrong path before realizing that the data tells a different story than your gut. Once they make the switch, everything changes.
The Counterintuitive Truth
In deal scoring, the best practitioners often do less, not more.
The lesson: timing is everything in this game. It sounds simple. It's incredibly hard to execute.
What I've Learned From 121 Companies
A few patterns in deal scoring come up again and again.
The founders who handle deal scoring well understand that the data tells a different story than your gut.
Lessons From the Trenches
I want to share a few specific lessons I've picked up over the years. These aren't theoretical. They come from real companies, real failures, and real successes.
Lesson 1: The best time to start thinking about deal scoring was yesterday. The second best time is now. Don't wait until you have the perfect plan.
Lesson 2: Hire for attitude, train for skill. The best people at deal scoring are rarely the most technically gifted. They are the most curious and persistent.
Lesson 3: Your competitors are probably getting this wrong too. That's your opportunity. While everyone else is following the same playbook, you can zig when they zag.
This connects to broader themes around revenue intelligence, AI sales tools, outbound AI, sales forecasting AI 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 deal scoring right on day one. You just need to get started and keep improving.
Founders who do well at deal scoring 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: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'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: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: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.