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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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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: What Are Your Top Tips to Building Your First Sales Team?

SaaStr

Dear SaaStr: What Are Your Top Tips to Building A First Sales Team? When it comes to sales hires, the key is to approach it methodically and avoid common pitfalls. Always hire at least two sales reps initially. It’s essentially an A/B test for your sales strategy. Trust Your Sales Leaders. For real.

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The 40% Problem: Do Your Sales Reps Really Cover All Their Accounts? And Is AI The Answer? With Yamini Rangan, CEO HubSpot

SaaStr

The 40% Problem: How AI Will Finally Fix Sales Coverage and Customer Face Time A wake-up call from HubSpot’s CEO Yamini Rangan on why your sales team is failing 60% of their accountsand how AI will change everything There’s a brutal truth about B2B sales that most founders refuse to acknowledge. Forty percent.

Scale 254
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A Look Back: How $13 Billion Ramp Began To Scale with Co-Founder and CTO Karim Atiyah

SaaStr

“Even with a bad hand, if the potential reward is great enough, taking a risk can make mathematical sense.” ” This framework can be applied across every aspect of building and scaling a company: 1. “Even with a bad hand, if the potential reward is great enough, taking a risk can make mathematical sense.”

CTO Hire 208
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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. 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. And where it will be very soon.

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88% of B2B IPOs Have Founder CEOs. And Those Ones Do Far, Far Better

SaaStr

Why Founders Stay: The B2B Advantage The 88% founder retention rate isn’t coincidental—it reflects fundamental advantages that founders bring to scaling enterprise software companies. Relationship-Driven Sales Cycles B2B sales are complex, long-cycle, and deeply relationship-driven. Filed, founder CEO.

Scale 184