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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. “Some teams consistently sold more enterprise SKUs, others had high volume but low ACV.

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

SaaStr

The AI-Native CRO: How Revenue Leaders Must Evolve or Risk Obsolescence 4 Top Learnings for Revenue Leaders 1. By the end of this quarter, team members who aren’t genuinely AI-curious should be let go. The 50/50 Team Is Coming Fast. CROs will need to manage teams that are 50% AI agents and 50% human by end of year.

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The Future of AI in SaaS Sales with Henry Schuck, CEO of ZoomInfo and SaaStr CEO Jason Lemkin

SaaStr

On the topic of building SaaS companies, Henry kicks off the conversation with: “I think a lot of bootstrapped founders who are less capital infused have to actually be great at developing their people. I bootstrapped ZoomInfo to 25 million in revenue. You need to be evaluating your team 100 percent of the time.

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Dear SaaStr: How Can I Crush a VP of Sales Interview?

SaaStr

Dear SaaStr: How Can I Crush a VP of Sales Interview? To nail a VP Sales interview, you need to demonstrate that youre not just a smooth talker with a great LinkedIn profileyou need to show youre the real deal. Heres how to crush it: Actually Know the Product Before the Interview.

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

SaaStr

The Infrastructure Bypass Midmarket software companies are caught in a “pressure cooker” with fast-moving AI startups developing applications far more rapidly than traditional software companies on one side, and tech giants investing billions in proprietary AI tools on the other.

AI Search 283
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CRO Confidential: The Hangover’s Over: 5 Ways to Get Your SaaS Revenue Back On Track with Gong’s SVP Sales and Founders Fund

SaaStr

Jameson Yung, SVP of Sales at Gong, and Sam Blond, Partner at Founders Fund and previous CRO at Brex, share five tactical ways to get back to growing and hitting revenue targets. The days of working a little for big returns are behind us in the Boom of ‘21, so what can you do to start hitting revenue targets? #1: Revenue matters, too.

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Scaling From $10M to $100M ARR: The Good, The Bad, and The Ugly with Showpad Co-Founder Pieterjan Bouten (Pod 586 + Video)

SaaStr

The $100 million in Annual Recurring Revenue (ARR) mark is a magnificent milestone for companies that indicates sustainable business growth. Scalability is about capability, so businesses need to understand whether they have the capacity to grow and whether their infrastructure and team can accommodate growth. Creating a category.

Scale 246