Enterprise Sales

“Selling is a relationship problem. Like you're not going to be able to sign a big deal. With a company, if you don't go and camp in their offices, if you don't meet them, if you don't actually like understand the problems, the constraints, the concerns, all of…”

“We spent a lot of time up front in our business, knowing we're going to do enterprise on making sure our procurement, your responses were super buttoned up. Right. We did our security, you know, our audits, all of these things that you would typically kick the…”

“Even if you're selling a, if you sell a 100,000 dollar solution, it is the same exact process to sell a million dollar solution.”

“And there's only two entry points starting at the very, very tippy top, meaning going direct to the decision maker, the chief legal officer, or finding the individual that would be maybe one step removed. Okay. I personally, other people would argue with this.…”

“Do not bring a recorder to this call. Do not record the call. They will not be open. They will not be vulnerable.”

“The fastest way to commoditize yourself is to go into some sales script, like budget authority, need timing, like that should be in the back of your brain. You never actually ask those questions.”

“There's always someone in the organization that's going to kill a deal. There's always somebody. You need to protect that as much as possible and make sure everyone is aligned and excited by what this is.”

“Co-author it with them. What does success look like? What are the specific things they should be doing? They should not just be logging in and meandering. That puts the work back on them. Your job in sales is to take all the work off their plate. 99% of it.”

“Try to hold out on talking about pricing until post demo, because you might, they might assume, oh, this is three times what I'm spending and not know why it's three times.”

“90%. Yeah. Because like enterprise sales is, it's mirroring their buying process. It's trying to control their buying process. It's not plopping these people into your sales process.”

“The win rate for enterprise, a good, healthy win rate. It's actually probably going to surprise you. It's not. Meaning of all sales qualified leads or opportunities with a healthy win rate is usually around 30 to 35%... 25 to somewhere between 25 and 35%.”

“I've had clients say to me like, Hey, like, I don't know if we're in a position to do this. And I've straight up said to them, you are a liability, not closing this gap. And they're like, sometimes they just need to be like, again, you need to know if you're i…”

“If you start talking to someone in the working level or talks with you in the first calls and you throw out too much that you came in through the CEO, this will not end well for you”

“I mean, I think enterprise sales for these large companies is much harder because the time to build the same exact product in house is just significantly lower. There's also just less leverage. Like when you're doing a negotiation against the customer for why …”

“I think that at any large-scale organization, those foundational principles will continue to exist.”

“None of the AI sequencing, I think we're past that, doesn't really work. You know, very much anymore in my opinion.”

“We kind of go against the grain, I guess, as it relates to running a playbook and doing just discovery and making sure that you're deeply embedded on that first call. What we find often is that we have to demo on that first call, and really just so that it con…”

“What makes it noble in my mind is are those companies where they feel like the sales team feels like they're not alone in the trenches. When the bullets are flying, the competition is trying to kill them. The product team is with them. The engineering is with …”

“If you really boil everything down to why people buy it, buy three things. They buy time, they buy money, and they buy promotions. It's that simple.”

“But I think ye olde enterprise sales, where there's actual trust built up between two carbon based life forms, I think will be very, very, very late to go in the white collar world.”

“Honestly, the only thing that's different today, it's exactly the same as it's been for a hundred years, except they call their SCEs or their system consultants For deployed engineers. The rest of it is the same. I thought it would be totally different in AI. …”

“Like, whenever someone's behavior in a business context doesn't make sense to me, I try to learn how they're paid, and usually the answer comes to the fore that way. And so, if you can just understand people's incentives, you can navigate around that and somet…”

“When you understand enterprise, you know, that it's also just never really about the product. It's about really understanding how you integrate into their processes, their workflows, their complexity of the environment.”

“I think enterprise sales will be a big one. So I want to focus much more on that. We are just like scratching the surface when it comes to that SEO has been proven to be very important also for people in our space. So we are going to be doing more of that. And…”

“And when you're doing enterprise sales, like you've got long sales cycles, your feedback is delayed. And it's kind of schizophrenic, because you'll get the feedback from the buyer during the sales cycle, which is more about the story and the promise and the bu…”

“Like a basic end user version, because that's how you get faster feedback. Like, otherwise I have to wait for a three months, six months sales cycle. And then I gotta go try to find the users within that company. And like, then my product development is going …”

“A long maybe will kill you.”

“I don't think that the art of the sale has really changed much, because there's an art to it, and then there's a science to it. So the art hasn't really changed, because you're dealing with people, and that can be, you know, dependent upon your style, and how,…”

“Selling them as service, even though the technology is powering it on the back end, is the fastest way to get your foot in the door. It's what they know how to buy.”

“So that's why the hundred K is such a safe zone because even for 10 K, you might have to go through procurement. So this is like the surest way to make sure that like you don't listen, I've seen 10 K take nine months to close.”

“Well, I, I'm a ten million dollar business. I'm like, in this small business space, you're zero dollars in enterprise. It's a zero to one right now in enterprise. It's a totally different game. It's a different value proposition. It's a different deal structur…”

“Inside, I'd like to see 90 days. Outside, six months. Reality is, it probably trends more towards nine months in enterprise.”

“Wiz is the only one I've seen do it successfully, where they started in the enterprise.”

“When you're trying to get something to happen in a large organization, it's never by just making somebody realize it's good for them. You have to have an understanding of what influence each player has over a certain decision, what incentive each player has ov…”

“Everything is very stodgy and everyone takes themselves very seriously, especially in this like enterprise sales, go to market space.”

“You can get to, I would say, 1,000,002 1,000,003 million of ARR, somewhere in there, for a lot of vertical SaaS businesses with that sort of self-serve model. Like, you can differentiate the pricing, and like, you know, you gotta figure out, there's a lot of s…”

“If you don't have three different people who tell you the same thing, you cannot believe it. So that's the hardest part about enterprise sales is how you get your spy network in place in the target company to really know what's going on. Because if you rely on…”

“I find almost every founder gets the ratio of enterprise to bolt on wrong, right?”

“The thing that was really, I think as anybody who's a founder in here, the thing that really mattered a lot was like, don't have two different cultures. Don't build an enterprise culture over here with like all the downsides of what we think of as enterprise c…”

“There's an initial consumer virality moment, and then that actually leads to lead generation in, Enterprise sales in a way that we did not see with the last generation of products.”

“So the right recipe for me, like, you know, if I had a choice, I would actually start both the motions simultaneously. Like, I don't want to actually Say that, look, you know, for the first three years, I'm, I will actually focus, you know on just being PLG an…”

“Though I do think, you know, maybe my hot take is like, if you're an enterprise business, you there, we have not automated sales yet. We've not automated enterprise sales yet. And so I do still think if you're working with enterprises where there's just like s…”

“It's only possible if you have a dialed in CEO Or kind of a C-suite who really gets it. If not, do not do it. You need a singular person who understands the emotion. If not, I wouldn't do it.”

“Fully believe that you need humans because customers want their problem to be solved. They don't give a F about products or services. They want their pain to be solved, and they want to build a non-transactional relationship with these vendors.”

“You always call the CEO day one, right? You never call lower. You call the CEO every single time, even if you don't get through, you know, for the stars, you'll land on the moon, right? So in general, we always go C-level, head of rev, CEO, Head of revenue, he…”

“If you're doing enterprise sales, I don't think you should build an audience at all, right? It should be all about like, it's selling.”

“In enterprise sales where I'm pushing, in magic box, I'm always trying to entice. I'm never, ever trying to push.”

“If you're selling a 3000 dollar tool, you absolutely want to be demoing as fast as humanly possible because it's a high volume game up market. When you're talking about hundreds of thousands of dollars, you want to slow that down as fast as possible.”

“If you're dealing with a highly regulated industry, Just know it's going to take a bit longer. Sometimes, 20 to 30% longer. So, like, a highly regulated industry, nine to 12 months on, like, conservative, on the conservative side.”

“Enterprises know that the process and the length to get the deal done is what costs more than the technology itself. Meaning the effort it takes to get through their system. That's why they're willing to spend so much, right? Like sometimes that's actually mor…”

“I would say anywhere between 50 to 200 K depending on the business unit you're selling to. That's kind of like sweet spot. Like they're used to something like in that realm.”

“Dave is talking there truthfully about like more probably corporate motivations. And so, and those are important, but they're also abstracted away from the motivations of the people you're actually selling to. And so Both of those are important. The ones that …”

“Over my experience over the past few years that very junior people can do very big deals with the right training and the right leadership. And that is very different than what most salespeople are taught is that only the most senior salespeople can do the big …”

“So if we're talking about the enterprise segment, you're gonna know within six, probably 90 days.”

“Inside, I'd like to see 90 days. Outside, six months. Reality is, it probably trends more towards nine months in enterprise.”

“A lot of people think if I nail PLG, then I'll nail enterprise. You can nail PLG and enterprise. I just would argue that nailing one does not necessarily make you more likely To nail the other. So if you can do both, but You gotta, in my opinion, you gotta sta…”

“Even the biggest tech companies in the world, when they're calling on the other biggest tech companies in the world, like you're going to have different requirements. They are a special snowflake. You're going to have to invest R and D dollars, which most star…”

“The skill necessary to get a million dollar deal done, there's so much in there in terms of like, how do I identify and build a good champion? How do I understand the political dynamics? How do I differentiate between an economic buyer, a technical buyer, an e…”

“In the real world, you're almost always selling to an individual human, not a big monolithic entity. And that's good news because humans are easier to understand than organizations. And that turns out to be really important. In the real world, sales is not adv…”

“All the best salespeople ask that question. On a first discovery call, Harry, when I'm meeting an enterprise customer, so tell me, is, is this purchase budgeted for this year?”