The Biggest Outbound Sales Mistakes Founders Make, Episode 3

“We’ve tried outbound but it didn’t work”, founders will tell me when we first meet. 

My next question usually is, “Great, how many campaigns did you send out?” 

“Uhmmm. 8 or 9, I think. But we didn’t book any calls from them. So we stopped.”

In the last 8 years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. I’ve done my best to help. And in doing so, I’ve spotted patterns: those costly outbound sales mistakes that keep occurring, and that prevent startups from growing to their full potential. Over 10 weeks, we’ll examine each of these very closely: at the pace of one per week. Consider this your mini-series on the biggest outbound sales follies founders make. And here’s your 3rd installment. Read on.

Founders give up on outbound after a few campaigns appear to fail.

Let’s start here. Sending out 8 or 10 or even 20 outbound email campaigns is not considered “giving automated email outbound a fair shake”. You have to give this sort of initiative at least 4 months of sending 4 to 6 campaigns out per week. 

Most founders don’t know the barometers of success when it comes to conducting outbound (more of that later). And then, they usually don’t possess the required rigor, grit, and patience to pull it off. When I tell them they need to apply themselves for that long, I usually get raised eyebrows, “Really? It can take that long?” 

Of course. Finding message-market fit is incredibly difficult. There are numerous permutations and formulations to try. You should commit to the long haul if you want your startup to make it.


Next week, we’ll look at a pitfall founders get caught up in mostly out of innocence and pride. It can come from a beautiful place but ends up damaging their chances to engage with prospects.