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What Order Should You Hire Your Management Team In?

SaaStr

IME, rough order to make hires in: VPM: $0.2m He asked which to hire first. If you have a few nickels in the bank, and you somehow find a great VP a half stage or even full stage early, just hire her. Hiring is so hard as it is. Make the hire now. ARR VPS: $1-$1.5m More here: [link].

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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. billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3

AI Search 283
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Be Careful Hiring “Dualies” — Folks That Are a VP of More Than One Thing

SaaStr

A VP of Sales and Success A VP of Sales and Marketing A VP of Sales and Anything Else. Is usually not really a VP of Sales. Sales managers back when I never managed sales. For signs the prospective hire just won’t work out, no matter how strong they might look on paper.

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What’s The #1 Challenge After $1m-$2m ARR?

SaaStr

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. Or churn will increase, NPS will stagnate and decline, and upsell and revenue retention will be a fraction of what it could be.

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If You Don’t Think You Need a VP of Product, VP of Marketing, Etc. — Then You Haven’t Worked With a Great One

SaaStr

I hear again and again from SaaS founders growing to $5m, $10m ARR or even more that they don’t need a certain VP — with the exception of a VP of Sales. Basically, in SaaS, everyone “gets” that they need a VP of Sales. Hire not just 1-2 reps, but 10. That it’s time to bring in someone that knows.

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Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders?

SaaStr

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. She can be your CTO forever.

Scale 269
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The SaaS Org Chart Live with David Sacks (Podcast #491 and Video)

SaaStr

You’ll need to hire aggressively to get to the next level and continue that rapid growth. But what roles should you hire for, and what will your org chart look like at each stage? In 2008, he founded Yammer, an enterprise software company that David grew to 500 employees and $60 million in sales. Head of Sales.

CTO Hire 278