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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. Subscribe now The Year of “Enterprise AI” One of the biggest challenges facing AI systems in enterprises today is the “last mile” problem: how do you make AI both reliable and accurate for specific enterprise use cases?

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Snowflake Buys Crunchy Data for $250m, Databricks Buys Neon for $1B. The New AI Database Battle.

SaaStr

Snowflake’s $250 million purchase of Crunchy Data and Databricks’ $1 billion acquisition of Neon represent a fundamental shift in how B2B software companies are preparing for the era of autonomous AI agents. With this news, we will be introducing Snowflake Postgres: enterprise-grade, AI-ready, and fully managed.

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IBM’s $7B Bet on Vertical AI and What It Means for SaaS Founders

SaaStr

Enterprise data is the differentiator: While public data dominates foundation models, enterprise-specific data represents less than 1% but delivers exponentially more value when properly leveraged. IBM’s $7B Bet on Vertical AI and What It Means for SaaS Founders.

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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. What does scaling Enterprise ARR mean? The Enterprise Funnel Finally, it’s time to scale as your experts become advocates and champions.

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🚀 Top 5 SaaStr Learnings from G2’s 2025 Buyer Behavior Report: You Gotta Be AI

SaaStr

AI Is No Longer a Nice-to-Have — 88% of power users won’t even shortlist software without AI functionality The Reality : 88% of power users won’t even shortlist software without AI functionality The Action : Stop treating AI as a feature differentiator. Align sales comp with net revenue retention, not initial ACV 3.

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How Enterprise Companies are Buying AI (or Not) with ContextualAI, Anthropic, Glean, and Unusual Ventures

SaaStr

At Saastr Annual, we hosted an Enterprise panel of AI leaders to share their experience and knowledge to help others understand how big companies think about and leverage AI. While the first generation of Generative AI is great, it’s not quite ready to solve Enterprise problems. What Are Enterprises Most Excited About Using AI For?

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

SaaStr

Selling to Multiple Stakeholders If you sell into the Enterprise, you understand there are different stakeholders. This gets more challenging when you have stakeholders who aren’t the ones buying the software. There was no software yet. When you’re “cheap,” you’re more immune to some of these effects. This is true for BILL.

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