Ray is one of our older salesmen, a grizzled veteran of the marketing wars. Being a grizzled vet, he’s been at a dozen or so companies over the years. The weirdest gig though had to be his time at Microsoft during the bubble.
He was a bit of a rising star at the time, and had attracted the attention of upper management, which at a company the size of Microsoft is a no mean feat. He was a human lamprey. A flatworm salesman who’d get pulled effortlessly into the intestinal tract of massive multinationals and come out the other end clutching millions of dollars of software licensing deals.
Gates himself pulled him into his office one day. He said he had a new assignment for him. Microsoft had conquered the industry. All that was left were companies making hardware for Windows, or making software that would run on Windows.
Like any emperor he did not have time to properly survey his holdings. His news came from sycophants, CEOs of companies that came offering tribute to avoid being crushed, or CEOs of companies that wanted to be bought. He needed someone inside, someone he trusted, to tell him what was really happening out there, in this bubble, this Cambrian explosion of internet companies with odd names and delusional business plans.

Ray told me all this through his first three whiskey sours. He had no one to talk to, to drink with anyway, now that Franz had gone, so he picked me. Why these dinosaurs, these fossilized executive cadavers have suddenly singled me out for attention I couldn’t say. Ray, like Franz before, may be making a horrible mistake, but it’s not my place, I’d guess, to tell him.

Two drinks later, after trying and failing to get me to explain why the coffee machine hated him, he told me the story of the first visit, the first travels he made for Mr. Gates.

“I traveled to a company that sold employee monitoring devices. RFID chips that tracked all employee movement, and software that created complex and beautiful visualizations that were displayed on the ceilings over the cubes, flowers that danced and twisted above the workers as they typed and got coffee and shifted slightly in their seats. Teams of accountants sat in the hallways, watching the patterns, looking for signs of who to fire in the flowing shapes.

They were their own biggest customer, and every quarter the company’s operating costs declined, something they were very proud of. They were, they said in their marketing literature, proof of their own success.

When the company ran out of engineers to fire the accountants turned on the HR department, then the executives. The last time I visited the VP of Finance was sitting alone in the hallway, watching the walls which, with both the patterns and employees that made them long gone, had shifted to steady and unmoving blue.”