Tales from other ‘verses, Part 2

In the beginning of the dot.com era, I joined a startup that “wanted to eat its own dog food,” which is a colorful way of saying “figure out how to use our own shitty technology before we force it onto customers.”

My job was to take a beta software product built with a beta programming language (Java) running on in a beta browser (Netscape) and build demos to convince our customers, who were in beta themselves, that they’d be better of buying our application rather than trying to implement one themselves.

We hired a Vice President of Sales. At the time, Denny was the only guy in the company over thirty. He had gray hair, a rarity in those days. As I had was successful in making braised dog food with a side order of fries, my role had morphed into field sales.

I spent a lot time with Denny on the road, playing the straight man when necessary. It was fun watching and learning from a master. [For example, Denny was an avid poker player. Since he was also an early-riser, what he'd do is let his stubble grow out somewhat, then get up at 3am to hit the tables. Other players would see him as "this poor, old man who'd been up all night" ... until he cleaned them out.]

Like any good salesperson, Denny was awesome at optimizing his income. If he’d receive accelerators based on the number of units sold, that’s what Denny focused on. This caught our 25-year old, first-time CEO by surprise because Denny was soon drawing more income than Roy. Roy reacted by adjusting the metrics. Needless to say, their relationship became acrimonious, often having shouting matches behind closed doors. At a small company, this was awkward.

After doing the “milk run,” a twelve-city tour over ten days, we had nailed a set of deals that put us 80% over quota. Instead of basking in victory, Denny was acting distant, quieter than usual. When we got back, Roy was taking a week off to go skiing. That Tuesday, Roy calls in from the lift and fired Denny, effective immediately.

Denny’s replacement, Janice, was a total sleaze-ball, but lacking Denny’s skills at prospecting or selling. She and I got off to a rocky start. Out of frustration from her constant meddling and sabotaging of my work, I left. She was fired six months later.