Mastering Enterprise Sales Motion

"In consumer, you're kind of like, 'Oh, we have a playbook for make the product work or make the feature work and make it delightful,' but I think in the enterprise, you almost have... Every time you think you have one use case, you have really two, which is how do you make sure that the feature works well and there's governance of the feature."

"And so the whole book is instead of trying to base the sales process on how we want to sell, we need to actually design the sales process on how they want to buy. And it seems like it's the same thing, but they're actually really, really different things."

"So in other words, they're on the same side. After the chasm, they say, 'I'm not sure about that, but we need what you have.' So transitioning from, 'We believe what you believe,' which is how you sell to visionaries to, 'We need what you have,' which is how you sell to pragmatists. That's the shift."

"They don't want to talk to you about you. They want to talk to you about them, and you need to ask them probing questions about them. Just like going to a doctor, you don't want the doctor to come and say, 'Hey, can I show you a movie of the operation I just did? I want to give you a demo. You mind if I give you a demo?' It's like, 'No. What I would like to do is talk to you about this pain I have in my side.'"

"I think as soon as you've got those 10 customers and more than 20% of your time is booked up with customers, you need leverage. You need leverage."

"So you need to hire one rep and you've got to hire two because otherwise, there's no A-B test. You have to A-B test humans."

"And so what's different is we now, I have a data scientist just like I did back in 2017, but I have a go-to-market engineer whereas before I just had someone in systems that was helping me configure outreach or sales off and my go-to-market engineer is helping me build an agent where we're coming up with, okay, well what's the human workflow that you would've done? And then how do you encode that using Vercel workflows as an example in actual code that's both deterministic and less so where an agent's going out and trying to replicate what a human might've done to produce that, fill in the blank, matlit."

"The experience that you have of being sold to will increasingly actually differentiate a company and drive buying decisions if products are only different at the merchant. And so then you really want to create a customer buying journey that feels like very unique experiences."

"You need to be vulnerable. I would be very open and honest with where you are. Hey, I'm an early stage startup. We have a lot to learn. Can we kind of gain your insight into how this problem is manifesting on your side?"

"The traditional sales stages that most CRMs are even set up as is you have your intro call. You have your second call, which sometimes could be the demo depending on the stage of market you're selling to. Then you have your third call, which is going to be more about walking through a proposal, a scope of work, maybe going deeper into the demo to contextualize it to everything you've learned."

"And then post-procurement, it's going to be obviously getting that signature and knowing who the actual signatory is. Sometimes it's not even the business unit, it's sometimes legal, CFO, procurement themselves. So just understanding who that is."

"They're not afraid of missing out, they're afraid of messing up. Dialing up the FOMO backfires 87% of the time."

"The challenger approach is about showing the customer what should be keeping them up at night. What's a risk that they don't know about but you do."

"A lot of deals kind of go sideways in that moment and the way this comes across in sales calls is that customers start, if you will, relitigating concerns that they had asked and you thought you'd address much earlier, like what might go wrong and is this really the right answer for us?"

"This is why Steve Blank always talks about startups can't get to scale without firing their first VP of sales, it's oftentimes because they skip that step, and so the founder's like, "Hey, man, I'm going to pour a little bit of sales on this, hire some sales leader or whatever, some sort of seller, and outsource this." You really just can't do that, not for the first couple dozen customers, it's just not tenable. You lose that feedback loop, you lose the learnings of whether or not your message fits the market, all that sort of stuff."

"You're playing a game of telephone with that with a third party seller versus even you just want to keep that in one brain to start, then package it, and then when you have a repeatable while loop, a selling while loop, then package it and hand it to someone else."