In my last newsletter, I wrote about my new framework, the Twelve Blockers to Product-Market Fit.
Today, I want to dig into the four blockers that hold founders back the most.
1. Selling to too many different buyers
This blocker is a key underlying cause of slow sales and GTM confusion.
A lot of founders think their customer definition is good enough, but the way those customers have been defined is usually too surface-level.
It's time to go beyond the tired ICP variables like "industry" or "job title."
You need to sketch out who might buy, what that buyer is trying to get done, and why the other ways of getting it done just won’t suffice.
If you have multiple hypotheses, you'll want to get them down on paper, stack-rank them, and strategically figure out which one has real demand.
Most startups don't do this. Most of startups sell to anyone. They have multiple hypotheses, and they pursue them all at the same time.
This approach exponentially increases the amount of noise that must be sifted through, causing downstream confusion, watered-down messaging, and a go-to-market strategy trying to please way too many buyers.
When you sell to anyone, you'll win a handful of deals, and then struggle to get the PMF flywheel spinning. Instead, isolate undeniable signal from one key buyer, and get great at winning them.
2. Using GTM tactics that don't work in the age of AI
I’ve been thinking a lot about how AI has ushered in a level of skepticism never seen before.
There’s so much AI-generated content that people are accusing content of being AI-created when it’s actually real. More and more folks are subscribing to the dead internet theory, or otherwise assuming that much of what they see online is fake, AI-generated, a scam, a "psyop," and so on… until they've got clear proof otherwise.
When it comes to reaching your buyers, you should expect that sky-high level of skepticism – especially because AI has enabled every single company to outbound more.
Your personalized AI outreach is, by and large, going to be categorized as “untrustworthy” within moments of your buyer seeing it. It doesn't compel action. It either goes unnoticed, blending in with all the other sales emails in their inbox, or it rubs them the wrong way.
We’re seeing this in the data: automated email campaigns like these have a 1 or 2% positive reply rate on average.
You shouldn’t settle for that paltry response rate. There are other options that work much better.
GTM tactics that are undeniably human (whether digital or in-person) are what’s getting results. This was true in 2025, and it’s even more true now that AI automation is reaching a fever pitch.
It takes more effort to generate leads this way, no doubt. But when you see up to a 30% reply rate to your outreach, having five sales calls a week, you’ll be glad you did it.
3. Poor process on sales calls
In growth-stage tech, there’s a kind of sales rep they call an “order taker.”
An order taker can close deals without doing much selling at all because the PMF is super strong.
A little light discovery, and poof -- the buyer is saying, “I want in. ”
The rep “takes their order,” so to speak, asking how many seats the prospects want to buy. It’s as simple as if the buyer was placing an order at the McDonald’s drive-thru.
There are no order takers in pre-PMF selling.
Even for companies I work with that are at $100K ARR+, they are absolutely not at the order-taking stage.
They’re still figuring out who is buying repeatably, and why. They’re still figuring out how to design the exact right deal cycle that reduces as much friction as possible, and reveals optimal amounts of intel.
There are many best practices that founders can follow during a sales cycle to increase the chances of winning the deal.
The rub is that they’re not easy to deploy.
I haven’t met a founder yet who deploys all of these best practices regularly – at least, not before a lot of coaching. Here are a few of them:
- Doing a sufficient amount of discovery (most founders don't do enough)
- Running discovery that feels conversational, rather than off-putting
- Only discussing your product after you’ve done baseline discovery
- Always running personalized, focused demos (no generic product click-throughs)
- Extending discovery beyond the first call, especially as other stakeholders get involved in the decision
- Pulling out objections and insights, instead of brute-force pushing the product
Learnable? Absolutely.
Kinda brutal to learn? Honestly, yes.
The feeling that comes from controlling your deals like this? Priceless.
4. Not enough deal analysis
There is a shocking amount of noise when you sell early-stage. It’s honestly maddening.
Think about just one prospect call. In this example (which probably feels familiar to you), let's say you had a discovery call. It went well, and the prospect said they were interested. But they went quiet, and never responded to any follow-up emails.
So, what happened? Here are just some of the reasons that could be behind their silence:
- They didn’t have the problem you solve
- They had the problem you solve, but didn’t really need to solve for it
- They had a problem that you could solve, but you pitched something slightly different, and they didn’t realize you could’ve actually helped them
- They tuned out because you were talking too much about the product, and now they're not sure if you can help them
- They got frustrated by your style of discovery and decided they don’t care enough to keep the conversation going
- You talked to the wrong person at the org or someone too junior, but that wasn’t surfaced and addressed on the call, so the deal lost steam
- They didn’t have what they needed to advocate for the purchase internally
- They had an objection that wasn't surfaced, so it wasn't handled
That’s so many potential reasons behind one closed-lost deal. What happens when you’re trying to make sense of ten, twenty, or fifty deals?
If we can't figure out why folks aren't buying, revenue will stay stuck, plain and simple.
This is why startups must analyze their deals.
Without analyzing won and lost deals, you’ll miss key insights about what kind of buyers have real demand and how to properly sell to them. It'll also be hard to figure out who you should stop selling to.
Through regular analysis, you’ll find the signal amongst the noise.
You’ll identify the attributes of a buyer who simply must have your product.
You’ll be able to isolate the issues with your sales strategy, and course correct sooner, rather than later.
I have good news.
In my upcoming Revenue Intensive, I’m going to help you overcome each of these blockers.
Starting on May 18th, we will have devoted sessions on the following topics:
- Who will buy your product, and why. We’ll go deep on identifying, defining, and stack-ranking the customer types most likely to buy.
- How to book sales calls when everyone's ignoring AI outreach. You’ll learn our foolproof framework for cutting through the noise and booking calls.
- How to run sales calls that close deals and surface the insights you need. You’ll learn our proven selling method and script that’s specifically built for pre-PMF sales.
- How to run deal analysis — and use those insights to find your must-have buyers and build a real GTM flywheel.
Pre-work comes in advance so we can spend our live time going deeper, workshopping, and building. After our three weeks together, you'll have made real changes to the most important parts of your growth strategy.
The Intensive takes place within my Repeatable Sales Club. Folks who join before May 15 will get 15% off with the code FIRSTMOVER.
Questions? Book 15 with me.
This is Extra Extra, a newsletter about the tactics and mindsets that drive early sales. I’m Caroline Fay, an exited social impact founder who’s spent my career launching and selling new products. I help non-traditional tech founders build sustainable, recurring revenue.
grow revenue ON YOUR TERMS
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Caroline Fay
