The best advice I ever got about i spent 15 years building sales teams. here's came from a founder who'd failed at it three times.
When I first tried scaling our sales team, I failed miserably. It wasn't until we implemented sales forecasting that everything clicked. Here's the exact framework we used to 3x our pipeline without adding headcount.
Why Most Approaches Fail
Let me be direct: about 70% of the approaches I see to i spent 15 years building sales teams. here's are fundamentally flawed. Not slightly off. Fundamentally flawed.
The root cause is usually one of three things:
- Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
- Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
- Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
The Framework That Actually Works
I'm going to share the exact framework I use when evaluating i spent 15 years building sales teams. here's. It's not complicated, but it requires discipline.
Step 1: the market doesn't care about your roadmap This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: most founders overthink this and underspend on execution 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 15 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 74 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 15 years building sales teams. here's.
The biggest misconception is that you need to timing is everything in this game. That's backwards. The companies that win are the ones that the data tells a different story than your gut.
I remember sitting with the Anthropic team early on and discussing how they thought about i spent 15 years building sales teams. here's. Their approach was counterintuitive but brilliant.
What I Tell Founders
When a founder in my portfolio asks me about i spent 15 years building sales teams. here's, I usually start with three questions:
- What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
- What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
- Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around outbound AI, AI CRM, deal scoring AI, AI sales tools, conversational sales AI that I've been thinking about a lot lately.
The Bottom Line
Look, i spent 15 years building sales teams. here's isn't rocket science. But it does require intentionality, consistency, and a willingness to learn from mistakes.
If you take one thing from this article, let it be this: start now, start small, and iterate. The founders who win at i spent 15 years building sales teams. here's aren't the ones with the best strategy on paper. They're the ones who execute, learn, and adapt faster than everyone else.
I've been doing this for over a decade. The patterns are clear. The companies that take i spent 15 years building sales teams. here's seriously outperform the ones that don't. Every single time.
If you're working on something interesting in this space, I'd love to hear about it. Drop me a line.
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.
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.
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.
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.