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AI Agents in B2B: Top 10 Learnings from Aaron Levie, CEO of Box and IBM’s VP of AI

Jul 4, 2025

At SaaStr's packed AI Summit 2025, Box CEO Aaron Levie and IBM VP of AI Raj Datta did a deep dive together with SaaStr's Jason Lemkin on how B2B companies should think about AI agents. With 10,000 attendees—a massive jump from last year—the energy around AI agents was...

Dear SaaStr: What Quota Should I Give to my Enterprise Sales Reps?

Jul 4, 2025

Dear SaaStr: What Quota Should I Give to my Enterprise Sales Reps? For enterprise sales reps, quotas typically range from 3x to 5x their fully burdened on-target earnings (OTE). This means if your rep’s OTE is $200K, their annual quota should be somewhere between...

The Latest 20VC + SaaStr: Rule of 80, 9-Figure Zombies, and the Death of Predictable Venture Math

Jul 3, 2025

We're back on 20VC, with Harry, Rory from Scale and SaaStr's Jason Lemkin. On on Figma's IPO, the AI transformation deadline, and why most B2B companies are already too late. https://youtu.be/ONAVeuKxzl0?si=8lQq-EkfhHRZdxxy The Bottom Line Up Front Jason's Rule: "If...

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