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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 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.

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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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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. The AI-Native CRO: How Revenue Leaders Must Evolve or Risk Obsolescence 4 Top Learnings for Revenue Leaders 1. The 50/50 Team Is Coming Fast.

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The Keys to Getting to $500M ARR In Just 7 Years with Attentive’s CEO

SaaStr

Here’s what it really took for Attentive to go from $0 to $500M ARR in just 7 years, sending over 32B text messages and generating $20B+ in revenue for their 8,000+ customers. CEO Amit Jhawar joined us at SaaStr Annual for a deep dive: 1. Solve The Hard Problem First And Patent It The first key insight? Black Friday playbook) 3.

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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. Too many VPs of Sales and CROs show up to interviews knowing almost nothing about the product.

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Scaling Success: Digital Entrepreneurship and SaaS Exits

FastSpring

Listen for the full insights into: How Flippa.com works to connect for-sale businesses with buyers while managing the complexities of valuation and seller expectations. When I was running it, it was a lot smaller than that, but scaled that up very, very quickly. And then of course you generate revenue in much the same way as a blog.

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