The Unexpected Reality

I thought enterprise sales was about selling. I learned it was about building a personal marketing organization at scale.

When I got my offers from Salesforce and Oracle on the same day back in 2007, I deliberately chose Oracle because everyone told me it would be harder. "Oracle is more legacy, more stringent," they said. "Salesforce will be easier." I wanted that explicit challenge because I believed that if I was going to learn sales—really learn it—I should learn from the machine that chewed people up.

What I didn't expect was spending my first week at Oracle sitting at a desk without a computer, reading a stack of sales books while waiting for IT to set me up. That's when it hit me: this wasn't going to be about charm or natural talent. This was going to be about systems.

Why This Experience Mattered

I wasn't trying to become a career salesperson. I was coming from IGN Entertainment where I'd been fulfilling advertising orders—not really selling. I wanted to understand how enterprise deals actually get made, how the best sales organizations in the world think and operate. My theory was simple: "Every job's a sales job," so why not get fluent in the language while I was young?

Between Oracle and LinkedIn (where many of the reps were also ex-Oracle), I spent three years inside what I now recognize as the most sophisticated revenue generation systems on the planet. I wasn't there to hit my number forever—I was there to decode the machine.

The Learning Laboratory

What I discovered was that Oracle wasn't just a sales organization—it was a massive funnel optimization engine disguised as a software company. The numbers were ruthless: every thousand leads converted to ten qualified opportunities, which converted to one closed deal. Nothing was left to chance.

My manager told me explicitly: "We're monitoring and judging you every minute of every day." You were a cog in the machine, but here's what fascinated me—it was a machine that worked. While other reps complained about being numbers, I started mapping how the numbers connected.

The approval chains were insane. Getting a deal through legal, finance, and management felt like navigating a byzantine bureaucracy. But I noticed something: the reps who succeeded weren't the ones fighting the system—they were the ones who had figured out how to work within it at scale.

My Systems Thinking Advantage

While other reps focused on individual deals, I became obsessed with the meta-game. How do you build a personal marketing organization within a larger sales organization? How do you create leverage when your day is measured in dials and emails?

I realized you couldn't scale one-to-one activities—cold calls, demos, negotiations. But you could scale one-to-many activities: webinars, email campaigns, thought leadership content that drove inbound interest. The best reps weren't just better at closing—they were better at creating pipeline flow.

Most importantly, I learned that qualification was more valuable than closing. "Qualify, qualify, qualify," became my mantra. You could be the world's best closer, but if you were working on deals that would never close, you were optimizing the wrong part of the funnel.

Key Insights Gained

Sales is a manufacturing process, not an art form. The romantic vision of the smooth-talking closer is fiction. What works is consistent execution of proven activities, measured relentlessly, optimized continuously.

You're selling to a system of people, not a person. Enterprise deals die because of misaligned incentives between departments, not because you failed to build rapport with your main contact. Understanding organizational dynamics mattered more than understanding individual psychology.

Revenue-generating activities. This Oracle principle became foundational to how I think about prioritization. Not all activities that feel like work actually move the needle. Ruthless prioritization becomes a survival skill.

How This Rewired My Thinking

Now when I walk into any organization, I instinctively map the systems before I worry about the people. I see information flows, approval bottlenecks, misaligned incentives, and optimization opportunities that others miss because they're focused on the surface-level relationships.

This perspective has been invaluable in every role since. In operations, I had deep empathy for what sales teams face on the front lines—the internal tooling problems, the approval delays, the pressure of feeding a funnel that's never satisfied. I could build systems that actually helped because I understood what the daily reality felt like.

What I Bring Forward

I can walk into any revenue organization and immediately spot the friction points between systems and people. More importantly, I understand how to optimize for compound effectiveness rather than just individual performance.

Those years taught me that empathy for sellers is rare and valuable. Whether you're in ops, consulting, or investing, if you're working with revenue-generating teams, having lived their reality gives you credibility and insight that's hard to fake.

The Bigger Picture

The goal was never mastery—it was building enough fluency to see the connections others miss. Those three years gave me a foundational understanding of how modern businesses actually operate at the system level, not just the strategic level.

Sales is hard. It requires putting yourself in uncomfortable positions daily, accepting rejection as feedback, and staying resilient when the numbers don't go your way. But more than that, it requires systems thinking at scale. The reps who succeeded weren't just good at selling—they were good at building personal operating systems that generated predictable results.

That's the capability I bring forward: the ability to see any business challenge through the lens of system optimization, combined with deep respect for the people operating within those systems. It's a perspective that only comes from being in the machine, not just studying it from the outside.