I think the biggest sales mistakes — twice — I’ve made at the CEO level is not being patient enough. As odd as that sounds.
In my first start-up (and really my second, too, but most importantly the first time) I shipped product too early to a Very, Very Large Key Prospect / Customer. Too early to meet the customer’s needs. This is always a tough balancing act in a start-up, and as founder, we’re biased to action. But if you aren’t sure you can ship an enterprise grade product to the Fortune 100 — maybe don’t until you are sure. We closed the small initial deal with the customer but lost out on the seven figure opportunity after that.
I did this again the second time around, just differently. I let a seasoned sales rep push something out, because there was too much going on and I trusted him. But in this case, the prospect was too large and while I trusted him, I shouldn’t have trusted his judgment on a key, early, Year 1 F500 prospect. We lost this key prospect/customer and never got it back.
It’s a tough trade-off and if I hadn’t pushed us to go to market fast, and release fast, and iterate, we would have gone bankrupt and failed — both times. But getting it just right with the very largest customers is tough.