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

SaaStr

Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth. “Some teams consistently sold more enterprise SKUs, others had high volume but low ACV. Shaping and maintaining company culture.

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

SaaStr

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. The performance distribution in sales teams will become dramatically wider, forcing tough talent strategy decisions.

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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.

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How Zapier supports 3 million users by investing in customer outcomes

Intercom, Inc.

But obsessing over efficiency can mask what’s most important, and most rewarding, to support teams – actually helping customers. Support teams exist to solve customers’ problems, not to deflect them or find the fastest way to hit the “close” button. In her own words , “When you take care of your customers, the revenue comes.”

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Scaling Success: Digital Entrepreneurship and SaaS Exits

FastSpring

In this episode of Growth Stage, we interview Flippa CEO Blake Hutchison about how Flippa works, as well as insights on what you should know if you’re a digital business owner looking to sell your business. How selling an investment business is very different from getting VC funding. Jump to video. | Jump to transcript.

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Top 10 Mistakes Getting to $100M ARR with LaunchDarkly’s Co-founder Edith Harbaugh (Pod 668 + Video)

SaaStr

After three months, this talented guy came to Harbaugh with the recognition that LaunchDarkly’s customers were developers. He didn’t like to sell to developers, so he quit. because they needed to rebuild the sales team. They rebuilt the sales team and closed some big deals. A bad one can torpedo you.

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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

Set and reinforce them early — as early as interviews. If someone is working hard but isn’t working out, invest in them and see if you can get them into the high-performing category. The underperformers who aren’t putting in the effort get a conversation, and if things don’t change, it’s not a good fit. Revenue matters, too.