The best advice I ever got about why my 12 years building sales teams changed when i used ai came from a founder who'd failed at it three times.
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
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with why my 12 years building sales teams changed when i used ai.
The biggest misconception is that you need to you should focus on one thing and do it exceptionally well. That's backwards. The companies that win are the ones that most founders overthink this and underspend on execution.
I remember sitting with the Anthropic team early on and discussing how they thought about why my 12 years building sales teams changed when i used ai. Their approach was counterintuitive but brilliant.
The Counterintuitive Truth
Here's what surprised me most about why my 12 years building sales teams changed when i used ai: the best practitioners do less, not more.
When I was building MovieLaLa, we tried to do everything at once. We had the best technology, the smartest team, and we still almost failed because we spread ourselves too thin.
The lesson I took from that experience, and from watching hundreds of other companies, is that 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
Most people approach why my 12 years building sales teams changed when i used ai with assumptions that made sense five years ago. The world has moved on. When I look at my portfolio companies, the ones that succeed are doing something fundamentally different.
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.
At RemoteTeam, we learned this the hard way. We spent months going down the wrong path before realizing that your team matters more than your technology. Once we made the switch, everything changed.
The AI Angle
I can't talk about why my 12 years building sales teams changed when i used ai in 2026 without mentioning 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.
I've seen companies use AI to 10x their why my 12 years building sales teams changed when i used ai capabilities. I've also seen companies waste millions on AI solutions that solved 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
The world of why my 12 years building sales teams changed when i used ai is moving 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.
And if you're a founder building in this space, remember that the best time to get why my 12 years building sales teams changed when i used ai 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
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.
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.
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 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.