Remove AI Remove Metrics Remove Underperforming Technical Team
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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. AI Curiosity Is Now a Firing Offense to Lack.

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

SaaStr

@Replit ’s ARR since founding The space is … beyond on fire No one is going to code without AI again pic.twitter.com/o9RYaYMBxq — Jason ✨👾SaaStr.Ai✨ And allowing more experienced developer to ship far, far faster. The company was caught in the classic freemium trap—massive user adoption but poor conversion to paid plans.

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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

And why the AI budget war is just getting started Top 5 Takeaways 1. AI is Eating SaaS Budgets : Companies like Cursor are generating massive revenue by replacing traditional SaaS workflows entirely. The Disruption Math Can Be Brutal : In contact centers, AI replaces 40-50% of human agents but only increases software ACV by 50%.

AI 259
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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.

Scale 254
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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. Turn Your Customers Into Your Marketing Engine The second breakthrough was making customer success the core growth engine. Black Friday playbook) 3.

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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. We’re now seeing the exact same dynamic play out in AI.

Cloud 167
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88% of B2B IPOs Have Founder CEOs. And Those Ones Do Far, Far Better

SaaStr

Founders typically possess: Original architectural vision for complex enterprise platforms Deep domain expertise in customer workflows and pain points Technical credibility with both engineering teams and enterprise buyers Product roadmap intuition built from years of direct customer feedback 2. Filed, founder CEO.

Scale 184