enterprise software
12 statements across 11 episodes · 5 bullish · 3 bearish · 11 people on the record · first statement Sep 22, 2022 by Elena Verna · across every show →
Everything said about enterprise software, oldest first
Sep 22, 2022 negative
Traditional enterprise sales motions battle utilization issues by selling before usage
“Then only after the purchase would some usage occur. And then you constantly battle utilization issues because you sell as much as possible to the entire organization. And then you have to catch up to that contract value in order to get the most value out of i…”
Dec 11, 2022 negative
Community isn't the top investment for high-touch enterprise software
“I think if you have a long sales cycle or a high price point where there has to be many, many, many touch points in order to get somebody to decide to buy, I'm not sure that community should be the number one thing that you invest in.”
Aug 10, 2023 positive
Miller: Mid-market SaaS focus prevents single enterprise clients from hijacking product roadmaps
“By playing in the mid market, it means our revenue is distributed more evenly across our entire install base, which means that there's no single customer who can hold us hostage really. But what that does is, you know, with great power comes great responsibili…”
Apr 4, 2024 positive
Shah: 'Reverse gravity' inevitably pulls successful software companies upmarket into enterprise
“In software, there's what I call reverse gravity. Over time, the market will always pull you up, right? Because what ends up happening is that smart founders and smart management teams will look at the numbers and say, oh, well, as it turns out, our bigger cus…”
Apr 18, 2024 bullish
Caldwell: LLMs will drive successful enterprise integration startups
“Likely LLMs will improve, like we'll probably be able to create better and better blue. So all sorts of software systems can talk to each other. And so again, very broad idea, but yeah, I think we'll see a lot of very successful companies where that's the kern…”
May 30, 2024
Dixon: Incumbent software vendors suffer more buyer indecision than startups
“Look, you guys, yes, it's tough to be a startup right now, early stage company. There's a lot of risks there, but who's offering more choices, them or you guys? You guys have a partner ecosystem. You have like, 20 different cloud products. You've bought like s…”
Nov 21, 2024 neutral
Jan 30, 2025 positive
Enterprise buyers can be convinced to drop software bloat requests
“What buyers care about is, is this going to make their team more effective, right? That's the reason that they're making this buying decision in the first place is that they're like, well, you know, the current situation we're in, and especially with larger co…”
Feb 2, 2025 negative
Tobi Lütke: Winning enterprise RFPs reveals nothing about actual software quality
“Enterprise software is Overfit to the sales process which is that it wins the RFPs because it has every feature ever, or at least a way of putting a checkbox next to every RFP line ever, but they don't, they're not good, right? Like, it's a great, an RFP is a …”
May 31, 2026 neutral
Evans: Enterprise AI software replacement will take three to ten years
“So I know people aren't going to tear out SAP and replace it with X, Y, Z. Maybe in five, in like three, five, 10 years, yes, that whole estate will look radically different. And all those jobs will have changed, but it will take, you know, two, three, four, f…”
May 31, 2026 neutral
Evans: Enterprise software sales take 18 months, exceeding VC funding cycles
“Enterprise software sales cycle is like, 18 months if you're lucky. You know, this is always a problem. The enterprise sales cycle is shorter than the venture backed startup funding cycle. Longer, longer, rather longer. Like it takes you longer to get an enter…”
Aug 23, 2026 positive
Abel: Charge for complex pilots and credit the fee upon closing
“Now, if you need something a bit more integrated and it, and it's a far more technical solution, what I'd highly recommend is do it for a month or two months, charge them for it, and then use that, that fee that you charge them for and credit it back to them i…”