Datadog’s Alex Rosemblat on the Importance of Really Knowing Your Customers

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Editor’s Note: This is the second half of a two-part interview featuring Alex Rosemblat. In the first installment, Rosemblat provides in-depth insight into how Datadog transforms non-technical sales hires into “almost engineers.”

Early Career War Stories

Sometimes, the “hard way” is the best way to learn a lesson. Take it from Alex Rosemblat, VP of Marketing for Datadog, a monitoring service that aggregates data from disparate sources to provide Dev and Ops teams with a unified view of large-scale application infrastructure typically running on a public cloud. Long before Rosemblat joined Datadog, he and a classmate at MIT’s Sloan School of Management partnered to create their first software product. Though the product solved a legitimate problem they each had encountered in their respective careers, it wasn’t proving viable in the market. Something was missing.

“In our previous companies, both my co-founder and I had struggled to find ways to efficiently leverage existing information rather than continuously searching for needles in a haystack,” Rosemblat recalls. “We both had experienced pretty big knowledge management problems, so we attempted to solve the issues we had encountered by creating a self-organizing knowledge management system that would turn any set of documents (including attachments in an email account) into the equivalent of a Yahoo! front page with categories that had to do with documents in a company’s file share.”

While his partner focused heavily on the technical side, Rosemblat coded components of the product while also setting out to find beta testers. Unfortunately, they couldn’t get anyone to sign on for a trial. Not even a free trial. “It was really frustrating,” Rosemblat says. “Everyone we talked to said, ‘Wow, this is really interesting. This could totally solve a problem for me,’ but then they’d say they had to get approvals from this person or that person when we would try to get them to actually try the product.” In the end, though people were interested and Rosemblat and his partner were talking to some big companies, the negotiations always fizzled out.

A conversation with an angel investor brought the problem into focus. “We were talking to an angel investor and he said, ‘You guys have a really interesting idea. It’s really cool that the prototype works for something so technically complex, but if I was to give you guys a million dollars right now to try and get customers, what would you do with it?’ My partner and I looked at each other and shrugged,” Rosemblat says. “We had no idea what we would do. It was only then that we figured out that we didn’t even know who specifically we were selling to.”

Career-Changing Epiphanies

After briefly exploring the idea of adapting their product to serve recruiters (a niche they weren’t excited about, but which seemed to be genuinely interested in their product), the two partners decided that it wasn’t the right time for them to start a company. But, something about the experience stuck with Rosemblat. “It really irked me that we’d missed something as basic as knowing who we wanted to sell to and why our product was of value to them,” he says. “It hadn’t even occurred to me that that was the first thing we needed to do.”

In retrospect, Rosemblat saw his mistake and realized it was something that happened all the time in the tech world. “It seems really straightforward,” he says, “But I’ve talked to a lot of people who have tried to start something and failed for this same reason. They get so enamored with an idea and think it’s important just because it solves a problem for them. They assume everyone else will see the same value, and their enthusiasm propels them to invest a great deal of time developing a product that they don’t even know if anyone is willing to pay for.”

A week after Rosemblat and his co-founder hung up their company, Rosemblat was recruited by the CMO for VKernel (a VMware monitoring solution that was acquired as part of Dell’s Cloud and Virtualization product family). Both the CMO and CEO of VKernel had a great deal of experience in sales and marketing. “If I joined the company, they would teach me everything they knew,” Rosemblat says. “An engineer might say that I crossed over to the dark side, but I’d felt the pain of trying to sell someone on something, and failing.”

As a result of his time working with and learning from the VKernel team, Rosemblat’s perspective changed, “Now, if you were to offer me a really good product with a so-so sales and marketing team, or a fantastic sales and marketing team with a so-so product, I would choose the latter.”

Applied Knowledge

Today, in his role as VP of Marketing for Datadog, Rosemblat brings all his experience to bear on how the company brings its product to market. “Datadog is a really, really technical product,” Rosemblat explains. “We sell to developers and admins who are deeply steeped in technology. If we make even the smallest mistake in the blog or some other collateral, people start tweeting about it. That’s not a joke.”

In addition to being hyper vigilant about accuracy and detail, Datadog’s audience is also savvy to typical marketing ploys. “If they see any hint of sales-y-ness or that you’re trying to serve them something fluffy that’s not descriptive and more in a B2C tone, they turn off and won’t trust you ever again. You’re done. You’ve burnt the bridge,” says Rosemblat.

So, how do you reach this kind of audience? You really get to know who they are and what they need, you speak their language, and you get super specific with your marketing. “You need to really understand the challenges that your audience is facing,” Rosemblat says. “This is a very savvy group of people who have specific needs. The tone and content employed in a lot of marketing campaigns aimed at main market users actually have a negative impact for these people. What has enabled me to have success at Datadog in terms of marketing is combining my previous technical background with the marketing knowledge I’ve acquired over the past years.”

A big part of Datadog’s sales process is demoing the product. The product is complex and supports integrations with more than one hundred different technologies. The team at Datadog needs to understand, in detail, why customers need each piece of technology and what problem each piece of technology solves. Rosemblat gets similarly “deep” with his marketing approach. “Every single marketing action that we take has tons of details associated with it,” he says. “Whether it’s Google AdWords or ranking for SEO terms, we get very granular for each technology and for modifiers of the technologies and the kinds of problems we’re solving for. We really drill down to the specificity of every single problem – and spec each one out, giving it detail and putting that detail into our demand-gen programs.”

That same level of granularity has to carry over from the marketing campaigns to the way salespeople talk to prospects. “If a generic phrase like ‘things of that nature’ comes out of any salesperson’s mouth,” warns Rosemblat, “I say, ‘Stop. Stop what you’re doing.’” There’s no place for gray area or generalities in Rosemblat’s marketing approach. “If a salesperson can’t be specific, it’s better for them to admit that they don’t know and let the prospect know that they’ll check up on the answer,” he says.

Brand continuity is another important element of Datadog’s marketing. “We make sure that the messaging that’s being put in an ad, blog post, or some other demand-gen program is what we use to train the salespeople working our trade shows,” Rosemblat says. “We also make sure that that same messaging is what prospects hear when they talk to salespeople on the phone. It creates a linear connection across the whole sales experience.”

Ultimately, Rosemblat’s goal is to align the entire company with the technical perspective that’s so important to Datadog’s audience of developers and admins. “It’s about using our internal conversations with our dev team to inform the way everyone in the company – technical and non-technical – sounds to our customers.” As an example of how this concept translates into on-the-ground tactics, new sales and marketing team members at Datadog go through an intensive training process for non-technical hires that culminates in a demo certification test. Each candidate is assessed by support engineers who determine if the individual is ready to represent the company by presenting demos to prospective customers.

If the company’s growth is any indication, Rosemblat’s approach is working. He’s come a long way since his first foray into marketing a software product, and his experience has served him and Datadog well. “You can have the best product in the world,” he says, “But if you can’t make the value clear to the audience that’s trying to find you, or you can’t put yourself in front of the person looking for a product like yours, you are never going to sell.”

Know who you’re selling to: understand their motivations, speak their language, and pay attention to the details that matter to them. This is how you build the bridges that a prospect wants to cross to become a customer.