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Dear SaaStr: How Do I Get a Job as a First Time VP of Sales?

SaaStr

Dear SaaStr: How Do I Get a Job as a First Time VP of Sales? If you’re aiming to land a VP of Sales role, you need to position yourself as someone who can deliver results and scale a team. "The "The biggest mistakes CROs and VPs of Sales make when they take a new role." Show you can recruit.

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

SaaStr

Finding and recruiting top talent is consistently ranked as one of the biggest challenges for growing SaaS companies. SaaStr Annual attracts thousands of high-quality SaaS professionals across functions like engineering, product, marketing, sales, and customer success. Meet and Find Your Next VP / CXO! Pull together the team.

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Dear SaaStr: Should I Move My Start-Up to SF Bay Area?

SaaStr

pic.twitter.com/IPZBNrz1jQ — Sam Altman (@sama) May 21, 2025 Here’s the rationale: #1. Whether it’s hiring a VP of Sales who’s scaled a team to $50M ARR or finding a product leader who’s built enterprise-grade solutions, the talent pool here is unparalleled. #2. — Hurley (@Johnsjawn) May 31, 2025 #4.

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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. The numbers are staggering: AI spending is set to hit $644 billion in 2025, growing at a mind-bending 76.4% year-over-year.

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The Top 10+ Questions to Ask a VP of Sales / CRO During an Interview (with New Cheatsheet)

SaaStr

One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. All the questions still hold today, but I wanted to update them for 2025. It’s a different world today, AI-fueled, often distributed and hybrid, and with inflation both in titles (CRO or VP Sales) and compensation expectations.

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“Talk to You in 2025”: When There Isn’t Budget

SaaStr

It’s the most common objection you’ll get in SaaS sales … Not Right Now. It can’t strategically improve sales software, financial software, quoting software, recruiting software, QA processes, call center software, etc. And when you hire a real, great VP of Sales. Truly qualified leads and prospects. I Don’t Have Budget.

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5 Nonobvious Learnings from Atlassian’s Path to The First $10B in ARR With Ex-CRO Cameron Deatsch

SaaStr

As we gear up for 2025 SaaStr Annual, May 13-15 in SF Bay , we wanted to do a deep dive on some of the best sessions from past Annuals. While competitors invested in huge sales teams, Atlassian actually restricted direct customer interaction. And we’ll see you at 2025 SaaStr Annual, May 13-15 in SF Bay!!