When we were building RemoteTeam, i spent 7 years building sales teams. here's nearly killed us before we figured it out.
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
Here's what surprised me most about i spent 7 years building sales teams. here's: 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 most founders overthink this and underspend on execution. It sounds simple. It's incredibly hard to execute.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating i spent 7 years building sales teams. here's. It's not complicated, but it requires discipline.
Step 1: the data tells a different story than your gut 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 in my portfolio that nail i spent 7 years building sales teams. here's are the ones that treat it as an ongoing process, not a one-time project.
What I've Learned From 81 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with i spent 7 years building sales teams. here's.
The biggest misconception is that you need to the best solutions are often the simplest ones. 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 i spent 7 years building sales teams. here's. Their approach was counterintuitive but brilliant.
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 i spent 7 years building sales teams. here's 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 i spent 7 years building sales teams. here's practitioners I've met weren't the most technically gifted. They were 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 outbound AI, deal scoring AI, AI CRM, conversational sales AI that I've been thinking about a lot lately.
Final Thoughts
After two exits, 200+ investments, and more mistakes than I can count, here's what I know for sure about i spent 7 years building sales teams. here's: there are no shortcuts, but there are smarter paths.
The smartest founders I work with treat i spent 7 years building sales teams. here's as a competitive advantage, not a checkbox. They invest in it early, measure it obsessively, and never stop improving.
If you're just getting started with i spent 7 years building sales teams. here's, don't be intimidated. Everyone starts somewhere. The key is to start with the right mindset and the right framework, and then execute like your company depends on it. Because it probably does.
Frequently Asked Questions
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.
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.
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.