How to sell to $10Bn enterprises as a 2-person team
Every enterprise is desperate for AI and their vendors can’t keep up. A small, prepared team can close deals with $10 billion companies. We know because we did it as a team of two.
Here’s the playbook we used.
Target C-level, not middle management
Managers are rewarded based on how many people they manage. Their seniority is tied to headcount. So when you walk in and say “our tool will make your team so efficient you’ll only need two people instead of six” – that’s a threat to their position.
VPs and C-level executives think otherwise. They’re measured on company-wide performance. They want an efficient story. They’re the most excited people in the building about AI.
So pitch them. Go straight to the top.
Write cold emails worth reading
Nobody’s coming inbound to a two-person team. Your only channel is outbound – cold emails and LinkedIn messages.
And no, cold email isn’t dead. Spam is. Every founder gets hundreds of templatised, zero-effort messages per day. They all go straight to trash. If the sender didn’t bother to personalise, you won’t bother to reply.
So do the opposite. Spend 20 minutes, 40 minutes, even an hour on one email. Study the person’s LinkedIn. Understand what they care about. Write something that could only have been sent to them.
It sounds crazy when everyone preaches volume. But when someone is that invested in reaching you, you feel it. And you reply.
Lead with dollars, not features
Technical founders love talking about what they built. The architecture, the stack, the features.
But C-level people think in one language: numbers. How much money saved, revenue gained, and time recovered.
Your email should read like: “I studied your company well. For department X, I believe our product will save you Y dollars per year – because A, B, and C.”
That’s the formula. Personalised research, quick maths, and appeal to a specific executive. And even if the C-level person doesn’t reply directly, they’ll forward it to someone on their team with a note to follow up.
Make personalised demo
Your cold email worked. You got a call. Now comes the demo.
Don’t show a generic product walkthrough. Study their company beforehand. Understand how they operate. Build your best guess of how they’d use your product, and show them that.
Will you get it right? Probably not. Maybe 80% of the time, what you demo won’t match what they actually need. That’s fine.
There’s a famous Palantir story from the early days. They were trying to sell to the CIA. They had no idea what CIA operatives actually did. So they built software based on their best guess and showed up to demo it.
The response was blunt: “This is nothing like what we do.”
Instead of walking away, the Palantir team asked: “What do you actually need?”
The CIA people started describing what they wanted. The team wrote it all down, went home, rebuilt the demo around those needs, and came back two weeks later.
It’s okay to be wrong on the first call. You just need to show that you genuinely care and are passionate about solving their problem. They’ll talk to you. They’ll tell you what they need.
You’re competing against people who don’t care
Remember that you’re not the only one pitching these companies. But your competitors are likely sending salespeople who won’t bother to personalise a demo.
They’ll show the standard pitch deck, run through the generic feature list, and move on to the next prospect.
You won’t do that. You’ll spend the time. You’ll do the research. You’ll build something custom. And that difference helps win the deal.
Selling to a $10B enterprise with no sales team sounds impossible. Until you do it. And right now, the conditions have never been better to try.
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