After a decade of investing in enterprise software, I've noticed something fascinating: While everyone talks about becoming a founder someday, almost no one discusses the tactical skills you need to master before making that leap.
That's why I'm launching "The Drafting Table" – a podcast and content series dedicated to uncovering the tactical skills that separate successful operators and founders from those stuck in the dreaming phase.
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After a decade of investing in enterprise software, I've noticed something fascinating: While everyone talks about becoming a founder someday, almost no one discusses the tactical skills you need to master before making that leap.
That's why I'm launching "The Drafting Table" – a podcast and content series dedicated to uncovering the tactical skills that separate successful operators and founders from those stuck in the dreaming phase.
How Great Startups Build Pipeline From Day One, with Alex Rosemblat, Advisor and Former CMO at Datadog
The Drafting Table
58 minutes 52 seconds
6 months ago
How Great Startups Build Pipeline From Day One, with Alex Rosemblat, Advisor and Former CMO at Datadog
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.
The Drafting Table
After a decade of investing in enterprise software, I've noticed something fascinating: While everyone talks about becoming a founder someday, almost no one discusses the tactical skills you need to master before making that leap.
That's why I'm launching "The Drafting Table" – a podcast and content series dedicated to uncovering the tactical skills that separate successful operators and founders from those stuck in the dreaming phase.
