SaaStr

JUNE 20, 2025

Prey Reality The AI Funding Explosion That Should Terrify SaaS Leaders Let’s start with the brutal math that should keep every SaaS CEO awake at night: $100 billion in venture capital went to AI startups in 2024 — an 80% increase from 2023 SaaS companies raised only $4.7 Tap the link in bio to watch the full interview.

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

SaaStr

OCTOBER 25, 2023

You’re not building a product or getting any new customers. In this interview, David Sacks talks about how 70-80% of investor time is spent looking at AI. Get a good CTO and commit to understanding your market and staying in the game. During the interview process, ask them who they’ll bring with them. It’s up to you.

Scale 284

Scale Sales Hiring Sales Recruiting AI 284

SaaStr

JULY 5, 2024

Some are decades-old problems, while others have emerged from this new world we’re in. Jason has sat in on interviews with 50-100 VPs of Sales, and many of them don’t even know what the product was in their 4th or 5th interview. Also, determine whether you have the right CTO to handle these changes. Let’s jump right in.

CTO Hire 209

CTO Hire Sales Hiring New CTO Venture Capital 209

SaaStr

NOVEMBER 11, 2022

But it was super interesting that the two big interviews I did were with Ben Chestnut from Mailchimp yesterday and with Dharmesh and Brian from Hubspot. Jason Lemkin: I think I noticed a pattern, and I wrote it up a couple of years ago and refreshed it, and then I’ll add a new anecdote. And I don’t mean in an edgy way.

Outsourcing Services 243

Outsourcing Services Banking CTO Hire New CTO 243

Sales Hacker

OCTOBER 13, 2020

Now, without further ado, let’s listen to this interview with Ryan Walsh. So, when a sales professional interviews at accompany, all of that information flows one way from the candidate to the company. Who is Ryan Walsh and what is RepVue? [02:40]. Sam Jacobs: Hey everybody, it’s Sam Jacobs.

Marketplace as a Service 111

Marketplace as a Service CTO Hire Sales Recruiting Scale 111

Intercom, Inc.

JANUARY 5, 2022

And then, in the 50s, they introduced this new thing, and there was resistance. Evernote’s CTO on Your Biggest Security Worries From 3 to 300 Employees. You can also read the full transcript of the interview, which has been lightly edited for clarity, below. Liam: The whole area is a new space. Caught your interest?

Scale 211

Scale Software Review compliance Technical Review 211

Sales Hacker

JANUARY 21, 2020

We’ve got an interview with Angus Davis. Now, without further ado, let’s listen to this interview with Angus Davis. About Angus Davis & Foundation Capital [1:45]. Sam Jacobs: Angus is currently a partner at Foundation Capital. Angus Davis: Foundation Capital is a Silicon Valley-based venture capital firm.

Payment Methods 61

Payment Methods Scale CTO Coach SMB 61