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The $939B Question: Is AI Eating SaaS or Feeding It?

SaaStr

The Great Spending Showdown: AI vs SaaS in 2025/2026 — What Every B2B Leader Needs to Know We’re witnessing the most dramatic shift in enterprise tech spending since the cloud migration began 15 years ago. Traditional legal software companies like Thomson Reuters have spent years trying to add comparable AI capabilities to LexisNexis.

AI Search 289
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AI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution

SaaStr

AI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution Lessons from Arvind Nithrakashyap, Co-Founder and CTO of Rubrik, on scaling cyber resilience platforms, building multiple product curves, and implementing AI across both products and operations.

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The Top 10 Reasons to Attend 2025 SaaStr Annual, May 13-15 in SF Bay!!

SaaStr

The event is strategically designed to facilitate 1000s of meaningful connections through 1000+ on-site “Who Do You Want To Meet” dedicated 1-on-1s for B2B founders and execs (no service providers, sorry!) VIP Networking app for B2B founders and execs attending (no service providers, sorry!)

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Top 10 GTM Mistakes Founders Make Again … and Again with SaaStr’s Jason Lemkin 

SaaStr

They hire a VP of Sales who doesn’t want to sell or learn the product. You also don’t want to hire a VP of Sales who won’t carry a bag. If you joined a startup at $2M and wanted to get to $6M with reps doing $400k, that VP of Sales would need to hire ten reps. 90% of the time, sales falls when a founder steps out of it.

CTO Hire 209
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Doubling Down: Erica Brescia, Managing Director at Redpoint Ventures

SaaStr

“Doubling Down” is a new series where we hear from top B2B SaaS investors on their most recent activities and takes on the current market. What’s your most recent disclosed investment? Jason Warner , who was CTO of GitHub before and during my time as COO there (and a former partner at Redpoint!)

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Taking a $4B Company from Consumer to B2B with Pluralsight (Video + Transcript)

SaaStr

We all know and could name several successful B2C and B2B companies. That was our first transitionary moment, and from that point forward, we began investing heavily in building a way to teach people technology skills outside of a physical classroom. So, let me walk you through that. That doesn’t sound too hard.”

B2B 173
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CEOs of Zapier, Walkme and Dialpad: How to Build Your First Management Team (Video + Transcript)

SaaStr

Which role should you hire for first? For starters, your first hire should be someone who can complement your skills, someone who is strong in areas where you’re weak, but it goes much deeper than that. I am guessing it’s probably the hardest problem to solve, hiring a job, let alone at this level. And for good reason.