enterprise software

18 statements across 15 episodes · 5 bullish · 5 bearish · 12 people on the record · first statement Feb 26, 2015 by Aaron Levie · across every show →

Everything said about enterprise software, oldest first

Feb 26, 2015
Insight
Levie: Inbound software models eliminated the need for immediate verticalization
“In the nineties and you had to sort of top down sell your software to get in, in the first place, then you had to make some really, really key early trade offs. Like you had to actually decide where am I going to get a flywheel effect going? And you don't real…”
Aaron Levie Feb 26, 2015 ▶ 56:34 Aaron Levie (Box): The First $250m in ARR
Jul 7, 2017 negative
Opinion
Agarwal: Most SaaS companies fail to build a meaningful second product
“If you look at the history of enterprise software and SaaS companies, you know, most companies rarely build a second product, you know, second product that's kind of as meaningful and as big and has as much potential as the first product.”
Ajay Agarwal Jul 7, 2017 ▶ 29:10 How to Break Out and Really Scale
Jan 3, 2018
Insight
Stewart: Enterprise deals are won on procurement process, not just product
“The lesson learned there is understand early on, you know, the answer to the question, which is, how do you guys buy software? Because when you attack those, it's never about the, ah, necessarily winning the technical end of it. It's gonna be about everything …”
Jon Stewart Jan 3, 2018 ▶ 4:41 Secrets to Closing Your First 6 Figure Deal
Jul 29, 2020 neutral
Insight
Lemkin: Enterprise software trends lag consumer technology by 4 to 5 years
“Maybe everything in enterprise sometimes is four to five years later than consumer.”
Jason Lemkin Jul 29, 2020 ▶ 39:54 What’s Changed Since March 15 The Cloud at Hyperspeed. The World in Flux.
Jul 29, 2020
Insight
Bernshteyn: Enterprise platforms must balance large-customer complexity with small-customer usability
“What we learned from our largest customers, Amazon being one and others is how to support massive complexity in the simplest way possible. And what we learned from some of our smaller customers is how to keep things very intuitive and user centric, but at the …”
Rob Bernshteyn Jul 29, 2020 ▶ 15:37 What’s Changed Since March 15 The Cloud at Hyperspeed. The World in Flux.
Nov 8, 2020 positive
Insight
Lemkin: Enterprise products need self-service to enforce product usability
“No matter how enterprise your app is, it should have a self-service component. Because if it does, you will be able to figure out how to get to the atomic element of this app without training, right? If you have no self-service, you can skip, you can have as m…”
Jason Lemkin Nov 8, 2020 ▶ 16:30 Going Upmarket, And How Things Have Changed in a Decade, at Trello, with Founder Michael Pryor
Dec 7, 2021 bullish
Prediction Not checkable as stated
Ghodsi: Multi-cloud support will be mandatory for enterprise software by 2023
“And I think this is a secular trend. So in a couple of years, I think it's going to be an absolute requirement. Like I don't want to, if your software only works on this cloud, I'm not sure I'm just going to be in this cloud.”
Ali Ghodsi Dec 7, 2021 ▶ 20:12 The Future of AI, Open Source, and Enterprise SaaS with Databricks CEO Ali Ghodsi
Dec 14, 2021 neutral
Insight
Investors buy platform stories, but enterprise customers buy apps
“The investor really likes the platform story to be told, and you can keep talking about the platform for the right audience, but that's not how customers will purchase or fund the project.”
Kazuki Ohta Dec 14, 2021 ▶ 36:35 $100 Million ARR Pivot: From Platform Product to Vertical Apps With Treasure Data CEO Kazuki Ohta
Oct 18, 2022 negative
Insight
Shah: Long enterprise sales cycles severely delay finding product-market fit
“Enterprise software sucks as a life. You've got these extended sales cycles. It takes you so long to figure out product market fit because you don't get as many data points back.”
Dharmesh Shah Oct 18, 2022 ▶ 5:31 The Secrets to Scaling with HubSpot's Founders Dharmesh Shah and Brian Halligan and SaaStr's CEO
Dec 20, 2022 bearish
Prediction Not checkable as stated
Liu: Classic top-down enterprise sales will become increasingly outdated
“I think that model is going to become increasingly, you know maybe not obsolete, but just It's gonna be increasingly outdated relative to this new you know, product-led approach”
Howie Liu Dec 20, 2022 ▶ 22:15 Scaling for the Enterprise: Top 5 Lessons on the Upmarket Journey with @AirtableApp CEO Howie Liu
Sep 13, 2023 bearish
Prediction Not checkable as stated
David Sacks: Expect widespread vendor consolidation as enterprise buyers cut costs
“We thought there were five or six different categories of, you know, sales enablement. They're all now trying to get into each other's business. And buyers are starting to sharpen their pencils and say, well, we just need one of these. And I think that's gonna…”
David Sacks Sep 13, 2023 ▶ 24:10 What the Future of SaaS Holds with David Sacks, Founder & General Partner, Craft Ventures
Dec 6, 2023 negative
Opinion
Levie: Consumer software is ten times more stressful than enterprise SaaS
“The consumer is just like 10 times more stressful because you don't have recurring revenue at any moment, like one single platform change. You know, can alter the entire dynamics of your business model. You're dealing with the whims and the mercy of the consum…”
Aaron Levie Dec 6, 2023 ▶ 2:06 What's New at Box with Aaron Levie, CEO and Co-Founder of Box and Jason Lemkin, Founder at SaaStr
Dec 13, 2023
Insight
Kellogg: High growth increases enterprise SaaS CAC due to ramping resources
“That's going to drive your CAC up because CAC is a function of growth rate in enterprise software because you're carrying unproductive slash ramping resources, right?”
Dave Kellogg Dec 13, 2023 ▶ 17:31 15 Signs You Have A SaaS Metrics Problem (and How to Fix it) with Dave Kellogg
Nov 4, 2024 neutral
Insight
Kellogg: Enterprise software manages pricing friction via consistency or complexity
“There's two ways to solve that problem. One is to have super consistent pricing, which in my experience in enterprise is very difficult. The other is to have very complicated pricing. So it's very hard for them to figure out who got the better deal.”
Dave Kellogg Nov 4, 2024 ▶ 51:03 What Really Matters in SaaS in 2025 with Jason Lemkin and Dave Kellogg
Dec 3, 2024
Insight
Holm: Enterprise software is inelastic, so vendors must set high initial prices
“In enterprise sales or enterprise software, it's not super elastic. That's the bottom line. Splunk may be one of the more elastic enterprise products than others, but you're not going to wake up one more, one day and say, oh, let's buy a bunch of Oracle today.…”
Karsten Holm Dec 3, 2024 ▶ 22:51 How to Leverage Pricing and Packaging to Drive Revenue with Miro, Loom, OpenAI, and Splunk
Jul 2, 2025 bullish
Prediction Not checkable as stated
Levie: Inter-agent communication will completely transform enterprise interoperability
“So the whole idea is what if you can have agents across your enterprise software talk to other agents in other enterprise software And I think for all of us as an ecosystem, this is going to completely change what interoperability looks like, what the future o…”
Aaron Levie Jul 2, 2025 ▶ 4:33 Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box 's Aaron Levie and IBM's VP AI
Jul 2, 2025 positive
Insight
Levie: AI transforms software's labor model, not just user interface
“Think about AI is actually a change to the labor model of using the software. So what can you do in a world where you can effectively create digital workers that That can go automate anything, you know, within the confines of your software.”
Aaron Levie Jul 2, 2025 ▶ 3:40 Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box 's Aaron Levie and IBM's VP AI
Jul 2, 2025 bullish
Insight
Levie: Bundling digital labor removes seat limits, expanding software TAMs
“So, so we can now effectively think about our software as having labor attached to it, which for all of us building enterprise software is like a completely mind bending, you know, concept where we're no longer just limited by the number of people that we sell…”
Aaron Levie Jul 2, 2025 ▶ 7:01 Why Enterprise AI Adoption Is Moving 5-10X Faster Than Cloud with Box 's Aaron Levie and IBM's VP AI
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