The Biggest Sales Mistake I Made. And I Made It Again and Again.

Q: What’s the biggest sales mistake you’ve ever made?

I think the biggest sales mistake I’ve made at the CEO level is not being patient enough. As odd as that sounds.  And I’ve made it at least thrice.

#1.  In my first start-up (and really my second, too, but most importantly the first time) I shipped product way too early to a Very, Very Large Key Prospect / Customer. Just way, way 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 a small initial deal with the customer but lost out on the seven figure opportunity after that.

#2. I did this again the second time around, just differently. I let a seasoned sales rep push something out to top prospects 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 due to a way too aggressive email, and never got it back.

#3.  Again, I almost blew a Top 3 tech customer due to impatience.  After 15+ onsite visits, dozens of demos, 4+ pilots, and 14+ months … procurement cut the annual price from $300k to $10k.  That was a bridge too far at the 11th hour.  Luckily, my new VP of Sales dove in and save the deal.  It ended up $150k a year.

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.

(note: an updated Classic SaaStr answer)