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Scaling Customer Success from 0-5,000 Customers with Drata’s VP of Customer Success and VP of Customer Experience

SaaStr

Most organizations lose around 10% of their revenue due to bad or poor customer experiences. For example, say your company is going upmarket to Enterprise. You need to look at your CS segmentation strategy, uplevel your CS team to be Enterprise ready, and do digital implementation in the lower market.

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The Journey from Freemium to PLG to SLG: Key Learnings from Dropbox, Salesforce and Vimeo

SaaStr

Companies successfully implementing PLG are seeing dramatically lower customer acquisition costs as a percentage of revenue. Plus, these motions are creating more predictable, sticky revenue streams. The infrastructure cost for real Enterprise readiness is massive. Who doesn’t want that?

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

SaaStr

The company reported more than 5,200 business customers using its AI capabilities weekly and achieved quarterly revenue topping $1 billion for the first time in Q1 2025exceeding analyst expectations. Snowflake’s Broader AI Strategy Snowflake’s momentum in AI is accelerating.

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The Playbook for Going Upmarket with Stripe’s CRO and Checkr’s COO

SaaStr

Enterprise buyers: Need predictability in pricing Want to buy solutions, not features Require modularity and customization Have completely different procurement processes The key is to repackage your components into enterprise-ready solutions. In 2019, top SaaS companies spent 50-55% of revenue on sales and marketing.

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5 Nonobvious Learnings from Atlassian’s Path to The First $10B in ARR With Ex-CRO Cameron Deatsch

SaaStr

The “Profitable Contradiction” Principle Fascinating paradox: Atlassian achieved higher enterprise penetration by making their products less “enterprise-ready” out of the box. Building a $10B ecosystem sometimes means doing the exact opposite of what enterprise software conventional wisdom suggests.

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The Wild Ride of Informatica: 32 Years, 2 IPOs, to $8 Billion Acquisition by Salesforce

SaaStr

Key insight: Even profitable, growing companies with real revenue can see valuations decline in different market cycles. private equity buyout (Permira + CPPIB) Company needed to transform for the cloud era Classic “take private to modernize” playbook 2021: Second IPO on NYSE at $27.55/share Market multiples compressed.

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What’s New At WorkOS and What It Takes To Be “Enterprise-Ready” in SaaS with WorkOS CEO and Founder Michael Grinich

SaaStr

In this new SaaStr series called “What’s new at…,” Jason Lemkin chats with WorkOS CEO and founder Michael Grinich about what it takes to be Enterprise ready in SaaS, building vs. buying, and who the stakeholders are in a B2D motion. They offer all the features you need to sell to Enterprise customers. It’s not an option.