Some of the best advice on AI sales tools comes from founders who failed at it first.
I struggled when trying to grow our sales team at first. Things only improved when we started using AI CRMs. I'll walk you through the approach that helped us triple our pipeline without hiring more people.
What I've Learned From 113 Companies
A few patterns in AI sales tools come up again and again.
The founders who handle AI sales tools well understand that most founders overthink this and underspend on execution.
The Counterintuitive Truth
In AI sales tools, 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 Reality Nobody Talks About
A lot of the advice on AI sales tools rests on assumptions that made sense five years ago. The world has moved on.
The first thing to understand is that most founders overthink this and underspend on execution. 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 your team matters more than your technology. Once they make the switch, everything changes.
The AI Angle
Any discussion of AI sales 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 sales 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 outbound AI, deal scoring AI, revenue intelligence, AI CRM that I've been thinking about a lot lately.
What's Next
Best practice in AI sales tools 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 AI sales tools 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:How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
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.