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Clouded Judgement - 3.28.25 - The New AI Risk Curve

Clouded Judgement

Data from Stripe (below) shows the speed at which AI native companies are growing compared to SaaS companies. Starting and scaling a software company was really hard. Starting and scaling a software company was really hard. If you wanted to scale users and growth, you needed to scale a physical data infrastructure footprint.

Cloud 299
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From $1M to $3B ARR: Databricks CRO Ron Gabrisko on Scaling a Revenue Rocket Ship

SaaStr

With Databricks now one of the largest pre-IPO technology companies, with $10 billion of expected non-dilutive financing and a valuation of $62 billion, Ron’s insights are gold for any revenue leader looking to scale. His view is your sales team teaches your customers how to get value out of your product.

Scale 182
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5 Great SaaStr Sessions with Databricks’ CEO, CMO, GM, VPP and VPS!

SaaStr

The Future of AI, Open Source and Enterprise SaaS with Databrick’s Founder CEO Ali Ghodsi: #2. “Lessons Learned in Scaling Databricks, AWS, VMWare and More” with Databrick’s SVP and GM Ed Lenta #3. The Top 5 Lessons Learned Scaling Databricks’ to $1.5B ARR with VP Product Nadim Hossain #5.

Scale 278
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The Complete Guide to SaaS Pricing Strategy

Tom Tunguz

The very best companies lead their customers in that dance. Many mid-market software companies price with the goal of revenue maximization, negotiating for the highest possible price in each sale. Penetration pricing leads to land-and-expand sales tactics. AWS, Twilio, Heroku, etc.

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Top 10 Reasons SaaStr Annual 2025 Will Be Better Than Ever!! May 13-15 in SF Bay!

SaaStr

It’s 50% about the intersection of AI + B2B, 50% about GTM in 2025+, and … 50% about helping you meet the best of the best! With a New, AI Demo Stage from 100+ Top AI Start-Ups! AI is transforming SaaS, and were dedicating two massive stages to the SaaStr.AI The SaaStr.AI Summit Is Back and Bigger.

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How Shopify Implements AI Across Sales and Product with Mike Tamir, Head of AI at Shopify, and Rudina Seseri, Managing Partner at Glasswing Ventures

SaaStr

At SaaStr AI Day , Mike Tamir, Head of AI at Shopify, and Rudina Seseri, founder and Managing Partner at Glasswing Ventures, level-set about where we are in the cycle for Enterprises adopting AI and the critical work being done at Shopify to leverage AI and solve real problems. The future of Enterprise is “Ambient AI.”

AI Search 293
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10 technical strategies to avoid when scaling your startup (and 5 to embrace)

Intercom, Inc.

This post is an adaptation of a talk I recently gave at the Amazon Web Services (AWS) community day event in Dublin about the technical strategies I’ve experienced that don’t work and the ones that have helped us to grow and scale at Intercom. At Intercom, we’ve found success running Lambda as glue code between AWS services.