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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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How to Train Your Sales Leaders: Key Learnings from HubSpot and BILL with Michelle Benfer

SaaStr

Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. “At HubSpot, I had over 100 frontline sales managers reporting to me.

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AI, Sales + GTM in 2025/2026: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton

SaaStr

At SaaStr + AI Summit 2025, Jason Lemkin and Kyle Norton CRO of $1B+ vertical SaaS leader Owner (where Jason is on the board) did a deep dive on AI in Sales today. This isn’t about being an AI expertit’s about demonstrating active engagement with AI tools and genuine interest in how they can transform sales outcomes.

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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.

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4 Things Most Founders Get Wrong About Marketing with Dave Kellogg

SaaStr

The 4 Things Most Founders Get Wrong About Marketing: “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. Better to hire for your specific needs and stage. These “five-five” CMOs barely exist.

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CRO Confidential: Moving Beyond Traditional Sales, Clay CEO & Co-Founder Kareem Amin on the Future of AI-Driven Growth

SaaStr

CRO Confidential podcast host Sam Blond chats with the CEO and co-founder of Clay, Kareem Amin, about two major topics: The evolution of Go-To-Market systems: where we are today with the incorporation of AI, and where we’re headed. They’ve achieved this due to the systems they’ve set up and the profiles they’ve hired for.

AI Search 269
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The $939B Question: Is AI Eating SaaS or Feeding It?

SaaStr

billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3 Industry observers like Josh Bersin remain skeptical about replicating complex systems like Workday’s payroll and compliance frameworks. billion total funding, $157 billion valuation Anthropic : $8.4

AI Search 274