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A Founder’s Guide to Building and Scaling Marketing Channels: Lessons from Datadog’s CMO and First Marketing Hire

SaaStr

At Datadog, their first focus was sponsored trade shows – specifically targeting the AWS ecosystem. Follow the Pilot-Repeat-Enlarge Methodology Pilot : Start small with minimal investment. Scaling Success: The Datadog Re:Invent Story Datadog’s experience with AWS Re:Invent demonstrates this approach perfectly.

Scale 247
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Clouded Judgement 12.1.23 - Net New ARR Starts to Rebound + AWS ReInvent Recap

Clouded Judgement

Subscribe now Amazon ReInvent This week Amazon had their annual AWS ReInvent conference. ” AWS fully embracing the breadth over depth approach. Looking at the mid to long term, we feel very optimistic about the outlook for strong AWS growth. I created this subset to show companies where FCF is a relevant valuation metric.

AWS 299
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Clouded Judgement - 3.28.25 - The New AI Risk Curve

Clouded Judgement

Fast forward to the launch of AWS and the public cloud. That juxtaposition is what makes investing in venture markets these days so fun! Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. So why try and compete now?

Cloud 184
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A Look Back at Q1 '24 Public Cloud Software Earnings

Clouded Judgement

Through these interactions, I’ve built up mental benchmarks for metrics on which I place extra emphasis. My hope is that this analysis can provide startup entrepreneurs with a framework for how to manage their businesses around SaaS metrics (e.g., This metric is more self-explanatory, so I won’t go into detail.

Cloud 318
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What Are Public SaaS Companies Taken Private At? 7.7x ARR On Average Per SaaSomomics

SaaStr

So one thing that has exploded in SaaS in the past decade is the role of Private Equity buying both public SaaS companies (to take them private, “fix” some metrics, and IPO or sell them again), and generally later-stage private SaaS companies. PE wants to invest in leaders, if not necessarily always #1 in a category.

AWS 321
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Clouded Judgement 10.11.24 - Budget Flush

Clouded Judgement

This behavior can create a surge in purchasing activity, as organizations look to make strategic investments without losing their allocated funds. Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. Cloudflare is up 17%. Mongo is up 16%.

Cloud 167
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Clouded Judgement 2.7.25 - "Group + Triage" AI Systems

Clouded Judgement

They each have some of the largest cloud businesses in the world in AWS, Azure and Google Cloud respectively. Given most software companies are not profitable, or not generating meaningful FCF, it’s the only metric to compare the entire industry against. Altimeter is an investment adviser registered with the U.S.