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Welcome Back Duplo Cloud & Pylon to SaaStr Annual 2026! 🎉

SaaStr

Duplo Cloud – Our 6-Time Champion! 🏆 A massive welcome back to Duplo Cloud , who continues their incredible streak as a 6th-time sponsor of SaaStr Annual! What Duplo Cloud Does : Duplo Cloud is the DevOps automation platform that eliminates infrastructure complexity for fast-growing companies.

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The Vertical SaaS Gold Rush: Why Non-Tech B2B Is Growing 250%+ Faster

SaaStr

Regulatory Requirements Create Infinite Moats Try switching away from Toast when you’ve got 50 restaurant locations with integrated POS, payments, payroll, and compliance systems. Try replacing Samsara when it’s monitoring your entire fleet for DOT compliance. Predictions for H2 2025 and 2026 1.

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Clouded Judgement 1.24.25 - The Year of Enterprise AI

Clouded Judgement

Every week I’ll provide updates on the latest trends in cloud software companies. For many current large language models, once they are exposed to domain-specific challenges or niche inquiries—like in-depth product troubleshooting or compliance-related questions—they can stumble. Follow along to stay up to date!

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AI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution

SaaStr

The Problem: Rubrik’s platform handles data across data centers, cloud VMs, databases, object storage, and SaaS applications. This committee evaluates AI tools and use cases for security and compliance before deployment. AI Adoption : Legal and compliance stakeholders should be partners, not obstacles 7.

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Approaching Half a Million Customers: How to Win in SMB with BILL CEO and Founder René Lacerte

SaaStr

He had the idea that the Cloud, not called the Cloud back then, would enable two entities to see the same transaction from their perspective. With a trillion in payment volume coming through BILL in the last five years, managing the payment and compliance engine has required an ongoing effort of a sizable team.

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A16Z: Enterprise AI Spending is Growing 75% a Year.

SaaStr

The Trust Shift : More enterprises are now hosting directly with model providers (OpenAI, Anthropic) rather than going through cloud providers—a complete reversal from last year when enterprises preferred cloud provider intermediaries for trust and compliance.

AI 206
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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. Cloud Giants Report Q4 ‘24 We now have the quarterly reports from Amazon, Microsoft and Google. They each have some of the largest cloud businesses in the world in AWS, Azure and Google Cloud respectively. The list goes on.