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What Really Works When Hiring VPs and Executive Teams with HubSpot Co-Founder and Chairman Brian Halligan and SaaStr CEO and Founder Jason Lemkin

SaaStr

The success rate for executive hires at high-growth SaaS companies can be surprisingly low – you’re often lucky if 50-60% of your management team works out long-term. ” If you have a SaaS company above 2 million in revenue, both Brian and Jason agree that at that point, all that matters is the management team.

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The VP of AI Trap: Why Hiring One Exec Won’t Transform Your Company. In Fact, It May Make It Worse.

SaaStr

” I saw a term sheet the other day where a leading VC firm reserved $1m of the round … for hiring a “VP of AI” Leadership teams scrambling to post job descriptions for “Head of Artificial Intelligence.” Would you hire a “VP of Internet” in 2010? Think about it.

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Why AI Has Taken Longer to Come to Sales Than Coding with Artisan’s CEO

SaaStr

Insights from Jasper Carmichael-Jack, CEO of Artisan at 2025 SaaStr AI Summit About Artisan: AI-powered sales platform building the end-to-end solution —from marketing personalization to AE automation across the entire revenue cycle. Sales is messier. CRM data accuracy sits at 47% across most sales orgs. The other 72%?

Scale 208
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The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do)

SaaStr

✨ Lemkin (@jasonlk) June 16, 2025 The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do, If You Use The Tools Properly) I get this question at least 3x a week: “Jason, we tried AI sales tools and they just don’t work. I’ve been in B2B and Saa sales for 15+ years.

Scale 265
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Hiring a Great VP of Sales: The New, Latest Edition with Jason Lemkin (Video + Pod)

SaaStr

What are the top 10 mistakes founders are still making today when hiring their VP of Sales? SaaStr CEO and Founder, Jason Lemkin, has done numerous surveys now that confirm that a startling 70% of first hires don’t make it. In this post, we’ll delve into the common pitfalls founders encounter when hiring a VP of Sales.

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How Windsurf / Codeium Built a Billion-Dollar AI Company and a Winning Sales Machine

SaaStr

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. Technical customers report that tasks that previously took weeks are now completed in hours.

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The Early Days: How Deel Went From $1m to $100m ARR in Just 20 Months

SaaStr

The Pivot : They interviewed 200 companies and 400 founders in just 6 weeks, asking one simple question: “If you’re open to hiring internationally, what are your biggest challenges?” Scaled Sales Without Revenue Operations (And Paid Dearly) The Explosion : From 2 AEs to 50 AEs in one year. ” Training was broken.