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

SaaStr

JULY 5, 2024

They hire a VP of Sales who doesn’t want to sell or learn the product. 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. You also don’t want to hire a VP of Sales who won’t carry a bag. 99% of the time, they probably don’t.

CTO Hire

SaaStr

OCTOBER 25, 2023

For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. In this interview, David Sacks talks about how 70-80% of investor time is spent looking at AI.

Scale

SaaStr

NOVEMBER 11, 2022

But as time went on, we shared lessons, what best practices were in customer success and revenue retention and all these things are, right. 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. And I don’t mean in an edgy way.

Outsourcing Services

Sales Hacker

OCTOBER 13, 2020

Instead, there’s one continuous streamlined customer-centric journey, leveraging the next generation of artificial intelligence, Outreach allows sales reps to deliver consistent, relevant, and responsible communication for each prospect every time enabling personalization at scale previously unthinkable. Are they hiring?

Marketplace as a Service

Intercom, Inc.

JANUARY 5, 2022

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. So we’re hiring across the board, all departments. Caught your interest? SOC 2 compliance: A Beginner’s Guide. The LinkedIn Incident.

Scale

Sales Hacker

JANUARY 21, 2020

We’ve got an interview with Angus Davis. Today’s sponsor is Outreach , the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best.

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