How Datadog Transforms Non-Technical Sales Hires into ‘Almost Engineers’

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During college Alex Rosemblat spent a fair amount of time in programming and database classes, but ultimately earned a business degree with a specialization in IT. Today, he is the 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 applications typically running on a public cloud. Although he realizes that some might say his transition from programming to marketing qualifies as crossing over to the dark side, his early experiences working with a variety of tech startups schooled him well in the value of good marketing. “My perspective changed,” he says, speaking of what he learned about marketing while at VKernel (a VMware monitoring solution that was acquired as part of Dell’s Cloud and Virtualization product family). “You can have the best product in the world, 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.”

Once you do have a prospect’s interest, you do however need to know how to best communicate with them, answer questions and match their problems to your solution. To this end, Rosemblat, has developed an onboarding process to transform non-technical hires into “almost-engineers.” Pairing a strong product with sales and marketing professionals who can speak the language of their highly technical audience has proven to be a powerful combination.

Building the Unicorn Hire

Rosemblat has always worked on highly technical products, and Datadog is no different. To sell effectively, he needs a team of marketers and salespeople who are fully versed in the lingo, the product use cases and the customer needs. Finding people with the right background for these roles can be a challenge, “Top sales or marketing candidates that are also highly technical are essentially ‘unicorns,’” says Rosemblat. “You won’t find many in the market and our team members need to have a solid understanding of technology to be successful.” Rosemblat overcomes this challenge by ‘building’ the unicorn hire with in-depth, continuous training.

Rosemblat’s training philosophy is based on pages he borrowed from the playbooks of companies like Epic Systems Corporation, which invests a great deal of time and money into up-front employee education. “We went through three months of training, nothing but training,” Rosemblat recalls of his early-career experience at Epic, now the leading healthcare software company. “The first month was training on the specific products we’d been assigned to, the second on how to do the different parts of your job. I even had a half-day training on how to run an effective meeting. That’s the kind of thing I don’t think a lot of companies really invest in, but a year after I started at Epic, I was a twenty-four year old involved in multimillion dollar sales and had been handed a great deal of responsibility. At Epic, that was not an unusual scenario, and I think the reason we were able to do it was that we all had undertaken so much training. It takes a lot of time and a lot of effort, but that amount of training gives people a huge boost to help them effectively do jobs that they had never done before.”

Based on these experiences, Rosemblat understood that the company could hire the best non-technical candidates available and help them become the team members they needed through in-depth and specialized training.

Onboarding on Steroids

“The first thing that happens within a week or two of a non-technical new hire joining,” Rosemblat says, “Is that they go through our extensive new-hire training curriculum. We run these each month and actually synchronize start dates so we can coordinate the training.” This may not seem to be such an innovative approach to onboarding non-technical hires, but it’s just the beginning of Rosemblat’s process.

For instance, he encourages people to attend the initial training twice. “Most people are usually really quiet in their first training,” he explains. “There are so many concepts and so much new terminology being thrown at them that I think that only a percentage of the material gets thoroughly digested. But after a month of being on the phones and immersed in the company, new hires have the foundation to start asking a ton of questions in their second training. This,” Rosemblat points out, “helps not only the returning recruits, but also first-timers who can piece things together more quickly based on the context of the questions being asked.”

In addition to that initial training, Rosemblat provides new hires with a series of on-demand videos and a weekly sales and marketing update in which the team covers not only new campaigns (so people know where their leads are coming from and how they should address them), but also deep dives into other market topics. “Every single week, our people get topped off with new knowledge about different kinds of technologies, new features in our products, or a change in the market,” Rosemblat says. “All of this helps them in their job.”

Demo Certification

After someone has been with the company for a few months, they are ready for Rosemblat’s comprehensive demo certification training. Compressed into several hours of intensive training, this course pairs new hires with support engineers and product marketers. The goal is to walk new employees through the standard demo in great detail so that they don’t just learn what to say, but also why each element is there to begin with.

“At this stage, new hires have the foundation. They get it. They’re able to start connecting a lot of the dots,” says Rosemblat. “Now it’s on them to practice every day until they can not only do the demo in their sleep, but also answer common questions, respond to less common questions elegantly, and tailor the demo to the prospect based off of details provided in a role play.”

The pinnacle of this training is becoming demo-certified. The process is tough. “Each person has to do a persona-based demo with one of our support team leads,” Rosemblat explains. “They do a discovery process and then slant the demo based on what’s most important to the prospect’s persona. The support team lead gives the candidate a qualitative thumbs up or thumbs down on the practical part of the test, which is followed by a written portion.

The Results

Once someone has been demo-certified by the support team, they are cleared to do fly-by demos such as you might see at a trade show where prospects are kicking the tires. “Getting demo-certified is a pretty big deal,” Rosemblat says. “They get a certificate, and for our non-technical reps, this is a huge milestone.”

While certificates and milestones are great, Rosemblat’s onboarding and training program is about a lot more than that. Rosemblat recalls visiting Datadog’s sales team in Boston and hearing a couple of sales reps debating about which new Datadog-supported technologies were their favorites. “They were giving really solid technical reasons for their choices,” Rosemblat says proudly. “They sounded like engineers.”

This newly acquired technical acumen also translates outside of the company. “Once someone gets demo-certified and are comfortable with the process, we put them at a trade show to demo the product and take questions from engineers,” Rosemblat says. “Almost every single time we’ve done that, the people we’re demoing to think that our salespeople are engineers. They have no idea that only a year or two earlier, the person doing the demo had likely not heard of AWS.”

Ultimately, Rosemblat would like to offer master classes for employees who are six to nine months into their careers with Datadog. “I have a list of about ten topics that come up and which are too technical for the sales team to be fully comfortable with,” Rosemblat says. “I’d like to go very deep into these topics so they can own them and talk to them like one of our support engineers”.”

These kinds of scenarios – the ones he’s seeing in the field and the ones he aspires to create – reflect the ultimate outcome Rosemblat hopes to achieve via robust onboarding and training for non-technical hires. “It’s so important to have everyone on the same page with a shared set of knowledge and speaking the same language,” he says. “The faster that you’re able to fully enable a new hire, the sooner they’ll be able to reach the potential they exhibited during the hiring process.”