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The Top 20 Symptoms of a Weak Development Team

TechEmpower SaaS

When speaking with founders and CEOs, we often hear concerns like this: My project manager is losing confidence in the development team. I think that poor communication and differing team cultures might be part of the problem, but how can I know for sure? These are the worries that keep team leads up at night.

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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 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. “The best hack,” Jason adds, “is not recruiting one management team. It’s recruiting five or six.”

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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.

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Product Judgment: How some people can repeatedly create product success

Intercom, Inc.

I hope this post allows people and teams to safely talk about Product Judgment. If you ever had to face a Manager, Director or Exec as they make bad product decisions and you’re struggling to persuade them otherwise, this post will help you. It takes years to build, and therefore ranges from very weak to very strong.