In Depth
Why your deals keep topping out at £20k
You built a business that closes SMB deals reliably. The demo works, the pricing is clear, and a founder or ops lead signs inside three weeks. Then a genuine enterprise logo shows interest, the conversation drags for four months, three new people join the thread, and it dies in "we've decided to revisit next quarter". That pattern is not a sales-skill gap. It is a recognition gap, and it shows up in a specific place.
Enterprise buyers do not buy the same way SMB buyers do. An SMB owner decides alone and rewards speed. An enterprise committee of six to ten people decides collectively and rewards safety, and safety comes from having already heard of you before the deal started. When a VP forwards your name to their CFO and legal team, someone in that group Googles you. If what they find is a tidy website and a quiet founder, you become the risky option that a mid-level champion has to spend political capital defending. Most founders read the stall as a pricing or feature problem and respond by discounting or building. Neither fixes the actual issue, which is that the room did not already trust your name.
The tell is in your win pattern. If your closed deals cluster under a certain size and every larger opportunity slows the moment more stakeholders arrive, you are not losing on product. You are losing on the founder being invisible to everyone in the room except the one person who found you.
What the enterprise committee is actually checking
There is a private conversation happening in every enterprise deal that you are never invited to. It sounds like "who is this person, and will choosing them make me look smart or make me look reckless?" The champion who likes you cannot answer that on your behalf with a deck. The answer comes from whether the other five people have independently encountered your thinking and formed a view before you walked in.
This is buyer psychology, not vanity. A head of procurement de-risks a decision by pattern-matching against reputation. If your name surfaces in their feed, in a peer's recommendation, or in a considered post that names the exact problem they are wrestling with, the internal story shifts from "unknown vendor a colleague found" to "the person in this space we already respect". That shift is worth more than any case study, because it arrives before you do and it comes from a source the committee trusts more than you: itself.
The founders who break through publish the thinking that a senior enterprise buyer reads and recognises as correct. Not thought-leadership fluff, but the specific operational judgement that only someone who has solved the problem at scale would hold. That is what earns you the benefit of the doubt inside a room you are not in.
How Underdog moves you up-market
We start with Voice Capture, a 90-minute session that pulls out how you actually think about the problems enterprise buyers lose sleep over. The point is to capture the judgement a senior buyer would find credible, the specific calls you have made that a smaller vendor could not, and turn it into a body of work that reads like you and lands with a committee rather than a solo founder.
Then Social Scout maps who is already active in your space at the seniority that signs six-figure deals, so your content reaches the VPs, heads of and directors sitting on the buying committees you keep losing to, rather than the SMB audience you already convert. Over three to four months this compounds: the right names start recognising your thinking before your reps ever email them, and the enterprise conversations open warmer because the room already has a view of you.
The trade-off is honest. This does not close next month's stalled deal. It changes the deals that start six months from now, because by then the committee has met your name three times before your first call. AI accelerates the output, but the insight and the voice stay yours, since a buyer can smell borrowed authority instantly. If you want faster, discounting still works, and it will keep capping you exactly where you are.