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Leading a GTM team

How does Datadog run bottom up and top down selling at the same time without the two fighting?

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 revenue retention reached 146 percent in the year before its IPO. 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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5 resources, 5 link-checked.

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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.

An Inside Look at How Datadog Reached $500M in ARR (and Counting)

From OpenView by Kristin Hillery Short read

  • Datadog runs bottom-up with individual developers and top-down with technology executives at the same time.
  • The product is built so a user knows what to do with it the moment they sign up.
  • Marketing's job is enthusiasm from the actual user, who then becomes the internal champion.
Open openviewpartners.com
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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.

Datadog: The Archetypal Example for SaaS Product-Led Growth

From aakashg.com by Aakash Gupta Long read

  • Datadog aims for 15 minutes to value from signup, one of its four product-led growth criteria.
  • It went from 100 paying customers at the end of 2013 to over 14,000 by the end of 2020.
  • Dollar-based net retention hit 141 percent in 2017, driven by land and expand.
  • Datadog spends more on product development than on sales and marketing, and 75 percent of new logos land with two or more products.
Open aakashg.com
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The best source on stopping the two motions fighting, with real penetration triggers and named cases where it went wrong, including GitHub losing a deal and Slack separating product teams.

The "$20M to $500M" Question: Adding Top Down Sales

From Andreessen Horowitz by Sarah Wang and David George About 15 min read

  • The signal to layer in top-down sales is 20 to 30 million dollars of ARR from the bottom-up motion.
  • Twilio watched for two or three departments using the product; Dropbox's tipping point was 3 to 10 percent employee penetration.
  • Two preconditions before hiring: the bottom-up flywheel works, and the business (not the user) is asking for more.
  • Individuals do not buy enterprise features, businesses do, so the product roadmap has to change too.
Open a16z.com
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It states the anti-conflict thesis directly: bottom up usage is what generates top down pipeline, so the two motions feed each other rather than competing for the same account.

Introducing enterprise sales to a product-led growth organization

From Bessemer Venture Partners by Janelle Teng and Elliott Robinson About 14 min read

  • Bessemer's threshold: explore a formal enterprise sales engine around 25 million dollars of ARR.
  • PagerDuty's net dollar retention was 139 percent at IPO, with historical cohorts consistently above 130 percent.
  • HashiCorp reached 2,100-plus customers and nearly 14 billion dollars of market cap at IPO in under eight years.
  • It splits prospects into pre-buyers and pre-believers, which are qualified and sold to differently.
Open bvp.com

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