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

SaaStr

The KPI Alignment System Have customers email explicit performance expectations Build custom reporting dashboards Weekly cross-team optimization meetings Formal performance reviews 2. Weaponize Customer Success Align on specific metrics Build education systems Create community Drive organic growth 3. Black Friday playbook) 3.

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SaaStr on 20VC This Week: Why 40% Cloud Adoption Marks the End of Easy Growth. And Why the AI Budget War is Just Getting Started

SaaStr

This isn’t just a statistic—it’s a fundamental shift that explains why your growth metrics don’t look like they did in 2019. When a development team switches to an AI-powered coding assistant, they’re not just adding a new tool—they’re often reducing their dependency on multiple legacy SaaS platforms.

AI 252
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From $10M to $100M ARR in 5.5 Months: Inside Replit’s AI Coding Rocketship

SaaStr

✨ Lemkin (@jasonlk) June 23, 2025 The $10M-$100M ARR Sprint: How Replit Became the Fastest-Growing “Vibe Coding” App (Or One Of The Fastest) A deep-dive into the AI development platform wars and why Replit’s 10x growth in 5.5 And allowing more experienced developer to ship far, far faster. 2023 : $2.4M

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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 244
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The SaaS Marketing Scorecard - How Does Your Marketing Operation Rank?

Tom Tunguz

The 9 Disciplines of Great SaaS Companies remains one of the most popular posts on marketing on this blog. Each bucket has a set of disciplines that the team scores. First, it enumerates the important priorities for a marketing team. sales enablement: how strong are the materials sales teams use to pitch? Comms Marketing.