Remove Engagement Remove Scaling Remove Underperforming Technical Team
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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. What’s great about high-volume sales at that scale is the pattern recognition,” Michelle shared.

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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. This isn’t about being an AI expertit’s about demonstrating active engagement with AI tools and genuine interest in how they can transform sales outcomes. The 50/50 Team Is Coming Fast. Just talking about AI isnt enough.

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

SaaStr

This wasn’t just an improvement it fundamentally changed how brands could engage with SMS marketing. The KPI Alignment System Have customers email explicit performance expectations Build custom reporting dashboards Weekly cross-team optimization meetings Formal performance reviews 2. Black Friday playbook) 3.

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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. Think about that for a moment.

Scale 254
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Is AI Penetration … Slowing Down? Ramp Says Possibly

SaaStr

Companies are discovering that hiring AI talent or upskilling existing teams takes much longer than anticipated. Many organizations are stuck in “pilot purgatory”—running successful experiments but unable to scale them. Integration challenges are mounting.

AI 281
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We Sent 4,495 AI SDR Emails in 2 Weeks and Got The #1 Response Rate. Here’s How (It’s Not What You Think)”

SaaStr

These weren’t cold prospects — they were website visitors, past attendees, and folks who had engaged with us before. We developed what we call “The Four C’s” for pre-call research: Chat : What did they discuss with our AI? SaaStr has been around since 2012. People know us. We targeted our existing database.

AI 229
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Clouded Judgement 7.25.25 - TAMs Lie

Clouded Judgement

What actually happened was this: Cloud created new pain points and new markets (more data, more sprawl, more teams), which made old categories more valuable. Cloud expanded access to tools that used to be too expensive or too complex for most teams. Not bad,but not world-changing. Cloud shifted services to software.

Cloud 167