2017
When I joined Cloudflare, I came from Akamai. I understood internet infrastructure. I understood the market. But Cloudflare was different — the platform was evolving fast, the product suite was growing, and the customers we were going after expected you to know your stuff.
Back then, we didn’t have Solution Engineers on every call. If a prospect had a technical question, you couldn’t just tag someone in and sit back. You had to know the answer, or at least know enough to hold the conversation until you could get one.
So I did the only thing that made sense. I sat with the SEs.
I soaked in what they did on a daily basis. I watched how they positioned the platform, how they handled objections, how they explained DNS, caching, WAF rules, and SSL configurations in a way that made sense to both technical and non-technical buyers. And most importantly, I asked a ton of questions. About everything. Relentlessly.
That investment paid off. I didn’t just learn the product — I learned how to speak the language. I could walk into a room with a CISO, a VP of Engineering, and a CFO, and hold my own with all three. That’s what won deals. That’s what built trust.
The best salespeople are the ones who actually understand what they sell. Not the pitch deck version. The real version.
2026
Fast forward eight years. I’ve earned President’s Club, been named Top Account Executive of the Year — twice — and I’ve helped some of the largest companies in the world secure and accelerate their internet presence. I know this platform. I’ve sold it at scale.
But the platform has changed. Cloudflare isn’t just CDN and DNS anymore. It’s a developer platform. Workers, Pages, R2, Durable Objects, Workers AI — this is where the growth is, and this is what our customers are building on. The conversations I’m having today are fundamentally different from 2017.
And I realized something: I was doing the 2017 version of selling a 2026 platform.
I could pitch Workers. I could explain what edge compute means. But I’d never actually deployed a Worker. I’d never set up Cloudflare Pages. I’d never experienced what our developers experience when they build on our platform.
So I decided to change that.
What I’m Building
This site — the one you’re reading right now — is built entirely on Cloudflare. No Squarespace. No WordPress. No origin server. Just Cloudflare Pages, deployed from GitHub, running on the edge across 300+ cities worldwide.
Total hosting cost: $0 per month.
I built it using Claude AI to write the code and Cloudflare’s Wrangler CLI to deploy it. I set up the DNS, configured the records, connected the custom domain, and deployed — all in an afternoon. I made mistakes along the way (I accidentally created a Worker instead of a Page — there’s a blog post coming on that one), and every single mistake taught me something I can now use in a customer conversation.
And I’m just getting started. The roadmap includes Cloudflare Workers for edge logic, Durable Objects for persistent state, R2 for storage, and Workers AI for intelligent features. Each one maps directly to a real customer use case I’m pitching right now.
Why This Matters for Sales
If you’re in sales at a technology company — any technology company — and you haven’t built something on your own platform, you’re leaving credibility on the table.
I’m not talking about running a demo environment someone else set up. I’m talking about starting from scratch, hitting errors, reading docs, figuring it out, and deploying something real. Because that’s exactly what your customers do. And when you’ve done it yourself, the conversation changes.
You stop pitching features and start solving problems. You stop reading slides and start sharing experience. You stop saying “our platform can do this” and start saying “I built this, and here’s what I learned.”
That’s the difference between a salesperson and a trusted advisor.
In 2017, I sat with the SEs to learn the platform. In 2026, I’m building on it myself. The lesson is the same: do whatever it takes to actually understand what you sell.
What’s Next
I’ll be documenting the entire process on this site — every build, every mistake, every lesson learned. Written for salespeople, by a salesperson. If you sell Cloudflare, or any developer platform, and you want to understand what your customers actually go through when they build on it, follow along.
This is the blog I wish existed when I started. Consider this the 2026 version of sitting with the SEs.