The Biggest Outbound Sales Mistakes Founders Make, Episode 2

“My product is not ready to sell.”

“Our website is not yet optimized for inbound traffic.” 

“I’m not sure we have the capacity to take on more than three customers per month right now. What if we get more interest than just that?” 

“We’re devoting our energies to nailing product-led sales right now. We’ll do outbound if this doesn’t pan out.” (This one has become a personal favorite of mine. It’s gotten trendy.)

All excuses not to get started with your outbound sales. I tell founders that it’s never too early to start working on your outbound sales. And frankly, I’d love to be able to shout it over the rooftops. 

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 2nd installment. Read on.

Founders don’t get started with outbound early enough.

Even when doing customer development, it’s helpful to unlock the motion that will get you in front of customers in a reliable way. Predictability in getting in front of customers is what’s called “Message-Market-Fit”. It’s the idea that you need to unlock the right message that will have your prospect respond with interest in having a first conversation with you. An arduous problem to solve; it can take some startups 6 months or more to unlock it. Getting started earlier rather than later is very much recommended. 

Message Market Fit is a crucial part of Product Market Fit but usually doesn’t the love it deserves from founders, I’ve found. Technical/product founders usually retreat to their strengths; to their product caves to code new features, when things aren’t lining up. Sometimes it’s not a product problem whatsoever. It’s the way the product is explained to the market. Instead of cranking out new features, we should be developing new copy variations to test in the market.

You could be a few months away from launching your product, and I would start setting up outbound experiments. You should go out with campaigns so you can iterate on those as the early results come in. I often recommend to my clients they start their outbound motion before starting product development. At the idea stage, getting in front of prospects repeatably without relying on your network is the best way to get unbiased validation of your product vision. That kind of feedback is invaluable and in effect greatly de-risks your startup early on. 

Unfortunately, I meet and work with founders often who don’t go through this risk reduction phase and rush into building product. Their customer development either is nonexistent or not rigorous enough and it becomes harder to find product-market fit when they are finally ready to go to market.

All of this to say that founders rarely start this exercise early enough. Even if the payoff is huge in product market fit risk reduction and revenue growth. At Whitetruffle, for example, where I ran sales, before dedicating myself to coaching startups, it took us 6 months to fully build out our automated outbound email initiative. It became our largest acquisition channel, responsible for 50% of our net new MRR every month.


Next week, we’ll look at something founders abort far too early. If they only knew what success looked like, they’d persevere, and, more often than not, come out on the other side.