enterprise sales

“Look, you know, it's not so superficial that we just look at the top line results, and that tells everything, because we're going to go inspect, you know, your activity levels, you know, and, you know, in other words, we're going to find out everything, and it…”

“So I think that is also another factor in this and small wins along the way, but larger wins are going to take six to nine months.”

“And I think the biggest change in venture and enterprise sales, because they're similar venture and enterprise sales actually have some similarities to them is that those first meetings are no longer done in person.”

“It's actually a lot easier to nail the sort of bottoms up motion first and layer on top of that more of a direct selling motion, I think than it is to come down market.”

“You no longer need to be on-site Every single time you need to meet with a customer. I used to be on the road at least once a week. I was always on the road. And yes, it's so important for relationship building, but it just, it doesn't need to be that way anym…”

“Trying to train folks that don't have the enterprise experience and convert them over, I don't think it's setting them up for success. I think you need to be able to find folks that have done this before that bring in the top end of the game and then having re…”

“You need to be introducing that implementation and that CS team before the deal is ever closed, right? Implementation, onboarding, how we're going to make you successful as a customer is part of the sales process.”

“I've seen mid-market account executives get promoted into enterprise in my past and flame out pretty quickly.”

“You don't need product market fit In order to sell an enterprise, especially as that first seller, what you need to find is product customer fit.”

“I see as a massive mistake people doing PLG and enterprise at the same time. They're almost too nervous to do one and commit and burn the boats on PLG or just be a top-down enterprise org. For me, I think that's a big mistake.”

“I also think it's because it's the product and growth mindset that's inherent within a PLG-led org where it's product first. And it's so difficult to imbue that in an enterprise org. Oh. And actually tacking on enterprise sales into a PLG motion, not as hard a…”

“If I'm running a PLG, like, don't waste your time getting into these cycles of, like, discounting and not, but if I'm running, like, an enterprise sale, I like to hold a high list and then figure out how I need to discount to still protect the premium and get …”

“I think you can, but I think it's extremely difficult. I think Slack was able to do it. I think they nailed PLG first, and then enterprise, but they always had an eye towards enterprise. The reason why I say it's extremely difficult is to capture the end user'…”

“Well, I think at first the sales team is, is obviously there for revenue growth, but almost even more importantly, providing customer feedback into the product group, giving the product team that they're working with a sense for why do these people gravitate t…”

“Everything about enterprise versus product led is different. Language is different. Messaging is different. Positioning is different. Customers are different. Product is different. Pricing is different. It really is a very different business.”

“There's a point where you really understand your product-led motion, where it is Measured. It is calibrated. You know what dials to turn to be able to optimize spend against acquisition. You understand how to optimize retention. Your retention life cycle motio…”

“The immediate gratification is, is definitely something that that I enjoy. But it's always like, it never ends, because once you have a good quarter, it's on to the next quarter, and you're a loser all over again, so.”

“Politicians in very large companies are always trying to find their next way up. So you've got to find people that are on their way up, not on their way out.”

“If they tell you they're the buyer, people will usually tell you they're the buyer. They typically aren't.”

“The three biggest hurdles in taking that holy grail of moving up into the enterprise, those massive ACBs, the sexy LTV to CAC, those sexy logos that you talk about, but the hardest problems. First, the credibility. No one knows who you are, especially in the e…”

“My rule of thumb there is you only get to have one of those until at least ten million, if not further.”

“This is where PLG goes south, is when you don't have the clarity in how you run the business of, this is our self-serve product, and this is our self-serve business, and this is how it works. And this is our sales-led business, and this is its value propositio…”

“It can be the other way of companies going trying to, you know, go into PLG from enterprise, which is a much harder path to go.”

“I would say when you feel market pull, when you feel the market, like I gave the example of Starbucks, you know, they're going past all of the processes, they're going past all, like they're seeking forgiveness, not permission to use your product. You're seein…”

“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?”

“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…”

“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…”

“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…”

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

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

“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 …”

“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 …”

“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.”

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

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

“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,…”

“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.”