A founder asked me last week about my guide to saas sales and marketing. My answer surprised them, and it might surprise you too.
The cloud AI space is complicated and always changing. I'm giving you a deep dive into AWS, Google, Azure, and the others, with my take on their strengths, weaknesses, and what they're planning. This is the guide every founder needs.
What I've Learned From 110 Companies
After investing in 200+ startups and running two companies to successful exits, I've developed a pretty clear picture of what works with my guide to saas sales and marketing.
The biggest misconception is that you need to customer feedback is the only metric that matters. That's backwards. The companies that win are the ones that your team matters more than your technology.
I remember sitting with the Anthropic team early on and discussing how they thought about my guide to saas sales and marketing. Their approach was counterintuitive but brilliant.
The Reality Nobody Talks About
Most people approach my guide to saas sales and marketing 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.
What I Tell Founders
When a founder in my portfolio asks me about my guide to saas sales and marketing, 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 cloud AI services, AI pricing models, usage-based pricing, serverless AI, AI infrastructure costs that I've been thinking about a lot lately.
What's Next
The world of my guide to saas sales and marketing 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 my guide to saas sales and marketing 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
Is this guide based on real experience?
Every recommendation in this guide comes from direct experience, either from building and selling my own companies, or from patterns I've observed across 200+ angel investments. I don't write about things I haven't personally tested.
Who is this guide designed for?
This guide is written for founders and operators who want practical, actionable advice rather than theoretical frameworks. Whether you're just starting out or scaling an existing business, the principles here apply across stages.
How often is this guide updated?
I revisit and update my guides regularly as I learn new things and as the market evolves. The core principles tend to stay stable, but specific tactics and tools get refreshed based on what's working right now.
How should I work through this guide?
Don't try to absorb everything in one sitting. Read through once to get the big picture, then go back and work through each section as it becomes relevant to your current challenges. Bookmark it and return to it regularly.