Big Deals: Why Team Selling Isn’t a Crowd Sport
Tea and TimbitsMay 06, 202600:25:1023.05 MB

Big Deals: Why Team Selling Isn’t a Crowd Sport

This week, we dive headfirst into the world of complex deals and team selling — and discover that the secret to winning big opportunities isn’t bringing eleven people and a 300-slide deck into a meeting. In fact… it’s usually the opposite.

We explore why complex deals are more often lost to internal chaos than to competitors, how healthy businesses create healthier sales processes, and why clarity beats noise every single time. Along the way, we talk about overloaded pipelines, managing urgency without panic, executive sponsorship, customer alignment, and the importance of having one person truly “own” the opportunity.

There’s also a cautionary tale involving eleven people heading into a defense contractor meeting… which thankfully became two people and three slides before anyone got hurt.

As always, we manage to make complex sales sound both strategic and mildly ridiculous — which, honestly, is probably the most accurate description of enterprise selling anyone’s ever come up with.