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Clouded Judgement - 3.28.25 - The New AI Risk Curve

Clouded Judgement

Every week I’ll provide updates on the latest trends in cloud software companies. Data from Stripe (below) shows the speed at which AI native companies are growing compared to SaaS companies. Fast forward to the launch of AWS and the public cloud. Now let’s talk about the AI wave. So why try and compete now?

Cloud 299
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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 249
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Databricks Just Caught Snowflake at $3.7B ARR. Here’s How They Did It (And What’s Next)

SaaStr

pic.twitter.com/VXSqDIuTZT — Alex Clayton (@afc) June 13, 2025 AI Fueling Unprecedented Growth Databricks just announced they’re targeting a $3.7 The AI Infrastructure Land Grab Is Real What’s driving this unprecedented growth? Every business process becomes an AI opportunity. Three things: 1. They were right.

AI 259
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AI is Already Remaking SaaS. 10 Trends To Watch Right Now. And Not Fall Behind On.

SaaStr

AI is already reshaping B2B SaaS, and its only going to accelerate. AI is Table Stakes Now. AI isnt a differentiator anymore per se its the baseline. Customers expect AI to be baked into your product, whether its automating workflows, improving onboarding, or delivering predictive insights. Mediocre AI wont cut it. #2.

AI 147
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Clouded Judgement 12.1.23 - Net New ARR Starts to Rebound + AWS ReInvent Recap

Clouded Judgement

Every week I’ll provide updates on the latest trends in cloud software companies. Subscribe now Amazon ReInvent This week Amazon had their annual AWS ReInvent conference. Couple takeaways for me: 2024 is shaping up to be the “prototype to production” year for AI. Follow along to stay up to date!

AWS 299
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The Complete Guide to SaaS Pricing Strategy

Tom Tunguz

AWS, Twilio, Heroku, etc. There are a few alternatives for AI-driven products: Triple the per seat price : If the AI agent is 3x as productive as a human, the software company could charge 3x as much per seat. Move to usage-based pricing : AI software might be priced like databases, charging for compute.

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Clouded Judgement 2.7.25 - "Group + Triage" AI Systems

Clouded Judgement

Every week I’ll provide updates on the latest trends in cloud software companies. Subscribe now “Grouping + AI” for Triage One area I’m quite excited to see AI revolutionize is “grouping + triage” workflows. Many of them AI based. Follow along to stay up to date! Perfect for a LLM!