enterprise software

8 statements across 8 episodes · 1 bullish · 3 bearish · 8 people on the record · first statement Jan 16, 2023 by Adrian Camara · across every show →

Everything said about enterprise software, oldest first

Jan 16, 2023 negative
Insight
Camara: Delivery-contingent enterprise contracts create massive startup risk
“Our first, like our first iteration of our first customers, they were contracts with deposits, but the balance was due on delivery of the product, which is when you're selling into, you know, mid market enterprise, that's super high risk because the definition…”
Adrian Camara Jan 16, 2023 ▶ 13:11 Adrian Camara, Founder of Athennian | How to do Customer Discovery · PMF Show
Mar 15, 2023 negative
Insight
Mass-market SaaS companies culturally struggle to pivot to enterprise sales
“The challenge is like when you're an everybody tool and you don't have enterprise in your blood it's a different way of being, right? Like you're doing sales driven motion... And if your company culture is a certain way, it's not easy to change your company cy…”
Aydin Mirzaee Mar 15, 2023 ▶ 37:07 Aydin Mirzaee, Founder of Fluidware (Bootstrapped to ~$100M exit) | How to Find Product Market Fit · PMF Show
Jul 17, 2023
Insight
Enterprise buyers trust hard cost savings over revenue uplift from startups
“So this first one, you can kind of easily build up in the early stages with a customer. If they spend enough time with you could say, this is what's happening today. Here's exactly what you're going to do in the future. I can build a case off of cost savings. …”
Nabeil Alazzam Jul 17, 2023 ▶ 24:46 Nabeil Alazzam, Founder of Forma.ai | How the First Enterprise Sale Leads to Product Market Fit · PMF Show
Aug 28, 2025
Insight
Donzé: Enterprise SaaS cannot have both fast sales cycles and high stickiness
“There's two things that you can't have at the same time. You can have a fast decision time, or you can have very high stickiness. You can't have both, because enterprises are very aware of the risk of the vendor looking, and so the more critical you are to an …”
Stéphan Donzé Aug 28, 2025 ▶ 35:24 He Bootstrapped to $55M in Revenue—without ever having to hit 100% YoY growth. | Stéphan Donzé, F... · PMF Show
Oct 16, 2025
Insight
Winning in new technology vacuums is a race to build brand recognition
“The other kind of journey is I think when there's a new area of technology that's a vacuum, and then people have no idea what to buy, but they're trying to buy something... It's sort of a race. To what becomes the industry standard. And the way to win there is…”
Dean Sysman Oct 16, 2025 ▶ 16:55 They failed every POC—then grew their cybersecurity platform to $100M ARR in 5 years. | Dean Sysm... · PMF Show
Nov 20, 2025 positive
Insight
Srugo: Fast, modest value beats delayed massive enterprise value in SaaS
“That's a huge one by the time to value, I think is an underrated, underappreciated concept just in general, like less value, but in less time, you know, a lot of times beats massive value in a very long time because you don't get there.”
Pablo Srugo Nov 20, 2025 ▶ 26:38 He left a $2B ARR company to build AI agents—then hit $1M ARR in < 6 months | Amit Shah, Founder ... · PMF Show
Mar 19, 2026 negative
Insight
Haroun: Enterprise software faces the most resistance from middle management
“What I found with my last company is sometimes it was like the junior person who's like day to day deep in the weeds. We did really well with, and then actually when we like skipped one or two levels and went to the top, they also really loved what we were doi…”
Omar Haroun Mar 19, 2026 ▶ 26:33 How he grew his AI startup from $2M to $20M ARR in 12 months. | Omar Haroun, Co-Founder of Eudia · PMF Show
Aug 10, 2026
Insight
Zima: Decennial enterprise software buyers prioritize vendor trustworthiness over brand prestige
“If you are establishing a 10 year relationship with a vendor in your mind, You want someone that you trust is going to operate well into the future.”
Colin Zima Aug 10, 2026 ▶ 24:28 He lost his first 5 deals—built the next Looker, raised $250M | Omni
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