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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. 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.

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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.

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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. This isn’t necessarily bad news for the AI market, but it does represent a significant shift from the explosive growth patterns of 2023 and early 2024. Integration challenges are mounting.

AI 269
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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.

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Okta’s Playbook to PLG, Developer Experience, and Enterprise ARR

SaaStr

Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. How do you build a stellar developer experience and continue to scale when the user base skyrockets overnight? Let’s start with product-led growth (PLG).