How Great Startups Build Pipeline From Day One, with Alex Rosemblat, Advisor and Former CMO at Datadog
Update: 2025-05-06
Description
Most founders think if they build a great product, the pipeline will magically appear.
It won’t.
In this episode of The Drafting Table, Alex Rosemblat (Advisor and Former CMO at Datadog) joins us for a tactical breakdown of how startups should actually think about marketing — especially in the early days.
We cover:
- Why “knowing your customer” is a cliché…until you realize you really don’t
- How Datadog thought about scoping, focus, and qualifying customers out
- What kinds of marketing campaigns actually worked — and which failed
- A simple formula any founder can use to figure out how much pipeline they actually need
- The biggest mistake technical founders make when trying to build go-to-market
- How Datadog transitioned from PLG to enterprise — and the hidden lessons they learned
Whether you’re just getting your first users or trying to scale to your first million in ARR, this episode will leave you with practical, non-obvious insights on how to build pipeline the right way.
Subscribe to The Drafting Table for more tactical conversations with operators, founders, and GTM leaders.
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