(un)learning sales

selling when you don't know what you're selling

A founder friend watched one of my sales calls for my new startup and was… confused.

He’d taken all the startup sales courses at Harvard Business School, read the (very good) Founding Sales book, etc. etc. etc.

He had learned a particular set of mental models about sales that felt like pitching, probing for pain points, persuading, demoing, PUSHING. As a result, he was stressed in sales calls, felt like he sucked at sales, and was worried that finding product-market fit was going to be next-to-impossible because of this.

My sales call, however, demonstrated no particular sales aptitude. It didn’t even SEEM like a sales call. But it still wound up with the prospect buying. Even better: It led to a step-change improvement in how we talked about our product and a clearer product roadmap.

Pre-PMF sales isn’t the sales you know and love (or hate).

Pre-PMF sales shouldn’t feel like sales

We approach founder-led sales totally backwards when we try to push our product using “traditional” sales approaches.

This doesn’t work well, in part because it makes everyone involved uncomfortable. Prospects feel us pushing and persuading (poorly). As a result, most stop saying what they really think. Ultimately they ghost us or give random excuses (“budget!” “let me know when XYZ feature is live!”), and we learn nothing. Worse, we learn the wrong things… then go build more product and/or hire “skilled” salespeople. And fail harder.

This is the direct result of following post-PMF sales approaches. They might work post-PMF, but they will PREVENT you from finding PMF.

I wish someone had slapped me when I was a total doofus trying to use Challenger Sales at this stage: “Really, Rob? Are you REALLY going to win by CHALLENGING your prospects when you’ve got like four semi-satisfied, occasionally-paying customers and have basically no clue what your business OR their business is?”

Pre-PMF sales is about learning where pull is

If you feel like you’re pitching, persuading, or presenting… you’re failing. In part because you’re not going to learn, and in part because you don’t know enough to pitch/persuade/present the right thing. This keeps you in the pre-PMF pain cave indefinitely.

Instead, I’ve learned (through pain) to approach pre-PMF sales as a CONVERSATION about a CASE STUDY.

You’ve probably seen Waffle’s case study deck (link HERE). What’s most important is that it’s not USED as a presentation deck or a sales pitch. It’s just a way to have a structured conversation that goes like this:

• “Hey, when I talk with founders & CTOs, they’re either trying to get SOC 2 compliant yesterday, or they’re planning for it sometime in the future. How are you thinking about that?”

• “I usually hear when they’ve bought Vanta or Drata, that they realize how many months of work it takes to get the product SOC 2 compliant and don’t want to become AWS triple black belts… what’s different for you?”

• “Sometimes I hear that teams consider delaying SOC 2, or hiring contractors, or just putting their heads down and refactoring everything, OR getting some solution that gets their product SOC 2 compliant automatically… what are you considering?”

• “When companies work with us, they get SOC 2 ready with just a few minutes of engineering work, and they don’t have to migrate off of AWS or anything. Is that kinda what you’re looking for?”

• “Oh yeah, how we do that, basically we just clone what companies already have in AWS, wrap it in our security layer product, and redeploy it into their AWS and it’s SOC 2 ready. Is that how you were expecting it to work?”

• “Cool - and if it’s helpful, here’s everything in one place - what you get, how others think about price, and what it actually costs. Companies can basically set this up themselves, but we tend to do it with them live so it really only takes a few minutes. If you were interested, the next step would be to do XYZ — you tell me though, is that worth doing?”

(Aside - if you want to have this conversation for your startup - email me - rob@reframeb2b.com. We’re even going to make a website soon. Big moves.)

These are the talk tracks for each slide in the deck. I can read this aloud in maybe 2 minutes. That’s all of me “presenting” (as you can see, in a way that doesn’t feel like a presentation or pitch). And the rest is just an unhurried, interesting conversation. They ask questions, they think aloud, we go on tangential rants about VCs, etc.

And if they lean towards buying, great. I help them do that. If they’re not a fit right now, I help them understand when they might be a fit, and send them on their way. If they need something different from what I have, great! I send them to the right business for their needs. And every time, I review the call transcript after the call to inch closer to PMF.

It doesn’t feel like a sales call because I’m not trying to sell - I’m trying to figure out what they’ll buy, and why. The difference matters. This approach tells me what to build, who my target market is, what pricing makes sense, what my growth approach should be, and the million other variables that will unfold.

So, yeah. Wish someone had told me this like a decade ago. Now you know.