6 Mistakes Founders Keep Making

20 months ago, I left a six figure job at a public software giant (monday.com) to work on what I believe is my life's purpose. Backed by a career in high-growth startups like monday.com, Fountain and Captify, I now help early stage founders crack repeatable revenue.

As a Fractional Sales Leader, I work with AI businesses to build the foundations so they can sell consistently, to the right ICP, and skip the mistakes I've made in 16 years in the field selling software.

Every week, that mission plays out in near-identical conversations. There's a moment that repeats itself almost word for word, whichever founder I'm talking to.

They have a good product. Sometimes a genuinely great one. Customers who use it love it. And yet the business isn't moving. They've tried selling it themselves. They've hired an SDR or two. Some have gone as far as bringing in a VP of Sales. And they still keep hitting the same wall.

By the time they get to me, the story is usually the same: no clear idea of who the product is actually for, messaging that shifts depending on who's in the room, and a seller (often the founder) who can talk about the product for an hour but can't get a deal to move without heavy discounting or endless "let me think about it."

None of this is a hiring problem, it's a foundation problem. Here are my field notes, 20 months into this journey.

1. "I'll fix sales with a hire"

The instinct when sales isn't working is to hire someone better at sales. So founders reach for a senior name, sometimes a VP straight from a recognisable logo, and hand them a business with no defined ICP, no process, and no system to plug into. Ten reps get hired off the back of that VP before anyone's proven the motion works once, repeatably, with one person.

Enterprise sales leaders rarely succeed in this environment, not because they're not good, but because the job they're hired to do (scale a proven motion) doesn't exist yet. The job that actually needs doing is building the motion in the first place. Most VP job specs give this away immediately: three bullets on sales acumen, twenty-five on technical domain knowledge.

VP number four will fail too, unless the foundation they're being asked to stand on gets fixed first.

2. "Our AI is for everyone"

Selling to everyone means selling to no one. It's the most common sentence I hear, and it's rarely said as a confession, it's said as a strength. Broad market, big TAM, no reason to say no to anyone.

The problem shows up downstream. Without a focused ICP, messaging can't be sharp because it has to work for too many different buyers at once. Targeting gets messy because there's no shared shape to who a good-fit account actually looks like. Everyone becomes a maybe, and a business full of maybes doesn't close.

The cost isn't just a slower sales cycle, either. Selling to everyone means the product roadmap ends up chasing every use case that walks through the door. Every new logo brings a slightly different problem to solve, and development ends up stretched thin trying to serve a market that was never actually defined. A focused ICP protects your sales cycle and your engineering team's time.

Not sure if your ICP is sharp enough? Try the free guide to finding buyers in your LinkedIn network with Claude.

3. "I need to pitch differently to each prospect"

This one's more subtle. Personalising a pitch is right, every deal deserves that. But too many founders and reps are also rewriting the core pitch every time, because there isn't a fixed centre to personalise around.

The elevator pitch should be crisp enough to repeat identically, every time, to anyone. What changes is the framing and the proof points you lead with. What shouldn't change is the pain point at the core of it, and that pain point needs to be deep and urgent, not a nice-to-have. If the core message shifts deal to deal, there's no message. There's improvisation.

The same discipline applies to the demo. A standardised demo, built once and refined over time, does two things a bespoke one can't. First, it builds genuine interest because it's been shaped by what actually lands, not improvised live. Second, it gives you a repeatable moment to build commitment: a clear next step the prospect agrees to before the call ends. Personalise the framing, keep the demo itself consistent.

4. "Why won't they just sign?"

Sellers need to understand how the businesses they're selling into actually buy, and so do buyers who are trying to get an AI tool approved internally. This gap is one of the most expensive I see.

Without it, a genuinely good AI product hits a price ceiling it shouldn't, gets bought on a personal card, and lives quietly in Shadow IT rather than becoming a real, budgeted, renewed line item. Deal control isn't a sales technique, it's understanding procurement, budget cycles, and who else needs to say yes before your champion can.

50% of winning the sale is understanding how your customer buys. For AI specifically, this is harder than it sounds, because the customer themselves often doesn't know. There's no established procurement path yet for most AI tools inside their business. Your job isn't just to sell, it's to find the most efficient path through their organisation and educate, empower and coach your buyer to get there. You're often building their internal business case for them.

5. "I don't need a playbook"

You don't need a full MEDDPICC process with an SFDC instance that has 15 custom fields nobody uses. What you need is a documented sales process with clear exit criteria at each stage.

Why it matters: a process is what tells you a deal is at risk before it goes quiet for three weeks. It's what tells you when to push harder and when to slow down and let a buyer catch up. Without it, every deal update is a gut feeling. With it, you have deal control, because you can see the system, not just the individual conversation.

6. "I can fix sales with the right tools"

It's easy to get hooked on the dopamine of a new tool. Sales software is built to be gamified, and adoption metrics reward founders for trying the next thing. But in nearly every engagement, the fundamentals matter more than the stack: seller behaviours, message clarity, a documented process, and optimising for time to value.

This is the same mistake as "I'll fix sales with a hire", just wearing a different outfit. Both reach for something external to solve something internal. A hire can't build an ICP that doesn't exist, and neither can a tool. Without a clear objective, messaging and ICP already in place, tools don't fix your gaps, they compound them, giving you more noise and more dashboards to manage while you slow down instead of speeding up.

Tools amplify a good foundation. They don't replace a missing one.

The pattern underneath all of this

Every one of these shows up differently, but they trace back to the same root: founders with a real product and no repeatable way to translate that product into buyer clarity. Not a talent problem. Not a hiring problem. A foundation problem.

Fix that first, and the next hire, whether it's an SDR, an AE, or a VP, actually has something solid to stand on.

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