How does Datadog run bottom up and top down selling at the same time without the two fighting?
The short answer
Datadog does both deliberately. Individual developers install the agent and get value in about 15 minutes with no salesperson, while the sales team works the executive buyer in parallel. VP of Marketing Alex Rosemblat put it as selling to the executive level while staying grassroots at the roots. The connection between the two is that the developers who already use it become the internal champions when the contract comes up, so the top down conversation starts with proof rather than a pitch. Then it expands: land on one monitoring use case, add application performance monitoring, logs and more, which is how net retention got past 140 percent. The failure mode most companies hit is bolting sales on before the bottom up adoption is real, which turns champions into gatekeepers.
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Why we picked it
Datadog's own VP of Marketing describing the dual motion and, more usefully, saying you have to actively reach out to the grassroots users so they will champion you in the contract conversation.
Why we picked it
Seven concrete lessons with the numbers attached, including the 15 minute time to value and net retention above 140 percent. The best single breakdown of how land and expand actually compounds.
