The Folly of Hunting Enterprise Whales
The Folly of Hunting Enterprise Whales
If you're in SaaS sales, don't go the way of Captain Ahab.
My Take:
At my first company, we sold software for algorithmic media monetization, but if you asked me what I did back then, I'd say I mostly hunted whales when I wasn't involved in product and people decisions back at HQ.
I did a 16 million dollar deal with Hewlett Packard. I did a 10 million dollar deal with Microsoft. Like Charlie Sheen, I thought I was #winning. Without even one lesson, I had become an enterprise sales ninja.
But after each hunt, I was exhausted. You slay the whale, you skin it, you field dress it and the village feeds for two months until the meat starts to turn. And then, it’s back to the boats to hunt again. It was fundamentally unsustainable -- there are only so many whales, and their numbers were dwindling.
It became clear that, to build a more valuable business, we needed to explore a larger ocean where more abundant, more catchable fish lived. At my next company, that became our focus, and we bagged all the $3-500,000 deals we could find.
Fast forward to today, where I and many others who've been at it for a while *lust* for a steady stream of $50k deals.
I learned this lesson, but it's increasingly clear that most in enterprise software salespeople have not. In fact, the majority of enterprise software sellers are completely unaware that the ground has shifted beneath their feet. They sit at the bar bragging about the time they bagged a $2.5M deal at Square or an $8M deal at Morgan Stanley. They remind me of the people from high school who loitered around campus after graduation, reminiscing about the big three-pointer they landed in a finals basketball game or the time they dated the prom queen.
Really, dude? Who cares?
So here’s the memo: If you work in enterprise software sales, you have to orient yourself to the marketplace as it is, not as you’d like it to be. The days of million dollar deals are mostly over. The question you need to ask yourself is: how quickly can you change your field motion, your customer engagement, your pricing and your packaging to meet the market? If you land a whale every once in a while, give yourself a high five! Kill a fatted calf and thank your deity of choice. But remember that chasing cetaceans alone is not a strategy, and if you want to play the game successfully in the long haul, you're going to have to triple your velocity and start chasing the fast-moving marlins, not just the slow, lumbering sperm whales occasionally spotted in deep Arctic oceans.
For enterprise sellers still lusting for olden times, it's time to get with the new, or face imminent extinction.
What I’m Reading:
Dialect prejudice predicts AI decisions about people's character, employability, and criminality VIA Cornell University
