Game of Thrones: B2B Marketing Lessons from the Epic HBO Drama with Datadog CMO, Alex Rosemblat

In this episode, we’re bingeing the epic HBO drama Game of Thrones to see what it can teach us about playing the game of marketing. Here to help us is Datadog CMO Alex Rosemblat. And together, we’re exploring how to win the battle by keeping your oath, using the rules of the game to your advantage, and putting your dragons to good use.

Episode Summary

Marketing is a game. It has its own players, rules and rewards. And the stakes are high. So we’re here to help you win the battle for the Iron Throne.

In this episode, we’re bingeing the epic HBO drama Game of Thrones to see what it can teach us about playing the game of marketing. Here to help us is Datadog CMO Alex Rosemblat. And together, we’re exploring how to win the battle by keeping your oath, using the rules of the game to your advantage, and putting your dragons to good use. So don your furs and prepare for battle as we charge into this episode of Remarkable.

About our guest, Alex Rosemblat

Alex Rosemblat is Chief Marketing Officer at Datadog. Prior to his current role, Alex served as the Product Marketer for Dell’s Cloud and Virtualization product family (via the acquisition of VKernel), bringing virtualization management and cloud monitoring software products to market.

Alex has 15 years of experience with enterprise software and related technologies through product management, IT consulting, and pre-sales engineering with Symantec (via the acquisition of SwapDrive) and Epic Systems Corporation. He has spent the last 8+ years at DataDog, and helped lead the company to its successful IPO in 2019.

About Datadog

Datadog is a SaaS-based monitoring and analytics platform for large-scale applications and infrastructure. Combining real-time metrics from servers, containers, databases, and applications with end-to-end tracing, Datadog delivers actionable alerts and powerful visualizations to provide full-stack observability.

About Game of Thrones

Game of Thrones is a massively successful epic fantasy series with an impassioned following. It’s about a civil war among noble families who are fighting for control over the iron throne that rules the lands of Westeros. Meanwhile an ancient enemy - the Night King - returns after being dormant for thousands of years. There are three major plot lines: the first is about the fight for the iron throne among the families. The second is about the rightful heir coming back to claim the throne. And the third is about the incoming winter, as seasons don’t have a worldly timeline, and so the summer has lasted something like a decade. The winter also implies hard times and the threat from the North, where the wildlings and Night King live. It’s based on the book series A Song of Ice and Fire by George R.R. Martin published in 1996. The series was created by David Benioff and D.B. Weiss for HBO. And it has a massive ensemble cast of over 500 characters. The show stars Emilia Clarke as Daenerys Targaryen, Peter Dinklage as Tyrion Lannister, Kit Harington as Jon Snow, Maisie Williams as Arya Stark, and more. It premiered in 2011 with eight seasons that wrapped up in 2019. That year, it was HBO’s most watched show and the most watched scripted show on TV, period. It had a total show budget of $1.5 Billion, and has earned $3.1 Billion through HBO subscriptions alone as of May 2019. It was filmed in the United Kingdom, Canada, Croatia, Iceland, Malta, Morocco, and Spain.

Key Takeaways

What B2B Companies Can Learn From Game of Thrones:

  • Keep your oath. And only market what you can deliver. It’s when you live up to your oath that you build trust and earn brand loyalty. Ian says, “If you say you're going to do something in your marketing, you better be damn sure that sales can deliver on that, that your product can deliver on it, and that customer success is going to be there if you fall short of that. Because so often we get out way over our skis. We're pitching a product that doesn't exist yet. And that's going to make people way madder than if you just didn't promise it in the first place.” So don’t break your oath like Jamie Lannister did when he killed the king. Ian says, “That follows him forever.” So keep your brand promise - or your “oath” - and deliver on what you market.
  • Play the marketing game. Be strategic in your marketing tactics. Experiment and use what works. And don’t overthink it. Small, steady successes are how you win the game. Alex says, “In demand gen sometimes you set up ads that are kind of gimmicky, and it'd be nice to do something a little bit more cerebral. But hey, you know, people like the jingle or, you know, whatever it is. And I think that there's a fair amount of pragmatism If you stick to that and you don't have this big ideology or this grand picture that you're trying to fill the pieces on. You just keep on stringing together successes of what works even if they're very moderate and small scale. Everything is a stepwise function, and you build your way up pretty high, just like Bronn does in the show.”
  • If you have dragons, use them. Don’t chain them up. Alex says that especially if you’re a startup, you need all the help you can get getting your brand off the ground. He says, “If you have any kind of secret weapon, you better use it. And you're probably going to want to use it pretty early on. You're not going to want to sit on it.” So call up your old classmates who are well connected. Leverage the talents and skills of your employees to make something great. For Alex, he said his secret weapon was that “I understood the persona we were selling to super well. And everything that went out the door was uniquely tailored to what a technical person would react well to. And the stats at the other end just kind of pop off the charts.”

*”Being good at growth marketing is being scrappy. Trying things out, not being afraid to lean into something even if it is a little bit hacky if it works. Never overstepping your bounds, and understanding that the world works a certain way.” - Alex Rosemblat

Episode Highlights


Watch Game of Thrones

Connect with Alex on LinkedIn

Learn more about Datadog

About Remarkable!

Remarkable! is created by the team at Caspian Studios, the premier B2B Podcast-as-a-Service company. Caspian creates both nonfiction and fiction series for B2B companies. If you want a fiction series check out our new offering - The Business Thriller - Hollywood style storytelling for B2B. Learn more at

In today’s episode, you heard from Ian Faison (CEO of Caspian Studios) and Meredith Gooderham (Senior Producer). Remarkable was produced this week by Jess Avellino, mixed by Scott Goodrich, and our theme song is “Solomon” by FALAK.

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