Diagnostic Pattern
"We cannot seem to win the bigger deals"
The symptom is real. The cause is usually somewhere else.
You can win your usual size all day, and the larger opportunities stall or vanish. It looks like a confidence, pricing or effort problem. It may actually be that a bigger buyer is a different job, and you are running the motion that works one size down.
What you think it is
We do fine at our usual size, but we cannot seem to win the bigger deals.
So you push harder, hire an enterprise rep to fix it, or discount to stay in the deal.
What it usually is
A hypothesis to test, not an indictment on you or the team.
Up-market is not the same sale, larger. The economic buyer is usually a different person from the one you sell to today, the evaluation involves procurement, security and references at your claimed scale, and delivery has to survive the commitments sales makes. In G.A.M.E. Plan terms the Goal changed but the Action - the strategy for how you win - did not, so the team executes the old motion harder against a different buying process. That is why effort and discount both fail to move it: neither is the constraint.
How to tell
Who on the team has ever closed a deal of the size and shape we are chasing? What did that process require that we do not have today - and who could have said yes in the last big deal we lost?
The move
Take the last three larger deals and map who was actually involved on their side versus who you talked to. The gap is usually the whole answer. Then decide deliberately whether you are changing the motion or changing the target, and resource whichever you pick - trying both at once is how teams end up doing neither.
You might think you need a better rep or a lower price. It may actually be that a bigger buyer is a different job than the one you are running.
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