Enterprise Software Sales

topic on 4 shows · 4 statements across 4 episodes

the Y Combinator Startup Podcast Innovators & Investors the a16z Podcast 20VC

4 statements about Enterprise Software Sales, every show

Chas Englander: Financial software sales require face time due to buyer career risk
“A lot of times you're speaking to folks that, you know, if they make a wrong call here, they could get fired, right? And so you spend a lot of time building that trust. I think the big part of that trust is, is FaceTime and getting in front of people, obviousl…”
Chas Englander Jul 31, 2025 ▶ 12:05 The Finance Startup Bringing Agentic AI to Wall Street · Y Combinator
Martin: Outbound cold-calling sales model no longer works in enterprise software
“That wasn't the case, you know, five, 10 years ago where you could just, you know, have a team of college kids, cold calling customers pitching, pitching their ideas. You know, that model unfortunately is, doesn't work anymore.”
Greg Martin Jul 16, 2025 ▶ 29:19 Revolutionizing Application Security: Transforming Risk Management and Facilitating Startup Success
20VC Insight
Bookman: Modern enterprise sales reps target seven-figure software deals
“10 years ago, 25, 50, 75 it used to be like, all right, get to a hundred K. Now I think kind of big league enterprise salespeople think a hundred K deals is like tic-tacs and we need to be targeting seven figure deals.”
Zachary Bookman Dec 6, 2024 ▶ 3:32 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
a16z Insight
Casado: Enterprise software sales faces a $30k to $150k 'valley of death'
“In direct enterprise software sales, it seems to be this valley of death between like, say, 30 K and a 150. If you're 20 K or below, you know, it, you can call somebody up and they can pay for it. And let's say if you're 200 K and above, then you have a hopes …”
Martin Casado Jan 2, 2019 ▶ 16:14 a16z Podcast | Monetizing Open Source (Or, All Enterprise Software)

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