The Importance of Having a Well-Trained Sales Team

Imagine a wall.

If you have an untrained sales team, and you say, “Go, go, go,” they will inevitably keep running into the wall and bouncing off. After running into the wall enough times, you have to step back and ask how to get over it. There might be a lot of ways: you might be able to bring a ladder, make a human ladder, fly over, or use a pogo stick.

It’s an analogy, but for Datadog’s VP of Marketing, Alex Rosemblat, this is what training is: teaching people how to get over the walls that they run into with buyers.

We recently interviewed Alex, and this post summarizes his responses to our questions on sales training.


Why Training Beats “Go, Go, Go” in Sales

You want more people to hit the ground running on your sales and marketing teams, obviously. This makes sense, but it can sometimes create more challenges than solutions.

Most sales leadership’s reflex is “go, go, go.” Their sales team’s hours spent selling are the most valuable way they can conceive to spend time. If it’s an inside sales team, they want their people on the phone, especially during business hours. If it’s a field team, they want them in front of customers on site.

So anytime you’re taking people away from phones or customers for anything is time that you’re not making your goal. And as everyone knows, for a salesperson, if you make and surpass your goal, really good things happen—but if you don’t, you might be looking for work.

Alex said he can understand the desire to maximize the time that people are doing their job. The thing is, though (especially for products that are very niche or technical), if your people don’t really know what to say or ask, you’re not going to get very far.

A lot of sales teams are graded on checkmark types of items. Sometimes those numbers are easy to gain. You could do 100 calls and have 100 conversations, even if none of them amounted to anything because you had no idea what you were talking about.

If a rep doesn’t come from your space, they’re going to have to learn all the ways of “getting over the wall” in your context in order to be effective.

Is the Importance of Sales Training Something Driven by a Couple of People at Datadog, or Is It Just Part of the Company DNA?


Alex joined Datadog before a sales team was formed at the company. So he started doing new-hire trainings and shaped culture the way their leadership wanted things from the beginning. This is obviously different from other organizations where people are entering sales and marketing leadership roles and have to change the existing culture.

Aside from that, his team is going to implement a worthwhile training, he gets the green light from his counterparts on the sales team. He’s learned that if someone really, really wants something, they will let you know. They’ll take out their checkbook or the equivalent, which for a sales leader is their team’s time.

So if Alex’s team is going to pitch something that he thinks the sales team should be trained on, if the sales leadership says, “Oh, yeah, we need that. Give it to us immediately,” they know they’re going to get the time for it.

If they’re lukewarm on it, that’s where Alex has to explore and see if maybe he got something wrong in his assessments.

After that, he sits down with his product marketing team to spec out how much needs to be covered for knowledge to get in people’s heads and how much time it’s going to take. They also do testing certification. They like to do role-play tests (oral exams), since this is the truest representation of selling to a customer. Then they’ll let sales leaders know who’s certified and who’s not.

They do continue to do trainings, and they run people who didn’t pass back through it. The goal is to have a really knowledgeable, well-versed sales team that knows the product, customer, and customer’s problem.

The Top Business Objective for Alex at Datadog

We asked Alex this question: “When you get up in the morning, what’s the top business objective at Datadog for you these days?”

It’s a lot, to be sure.

“At the end of the day,” he said, “we’ve made a product that fits the market.” They’re very reactive to what customers and prospects say they need.

So if their product is so widely applicable to people who need it, it’s about how to get in front of them to let them know that such a product exists. He wakes up every day thinking, Is there another pocket of people that I wasn’t aware of that need the product?

The sales enablement piece obviously factors into it, because once he finds those people and they’re interested in learning more, sales better be ready to talk to them.

What is most effective when someone is trying to sell to you?


We like to ask all of our podcast guests this question. Here’s how Alex responded:

“Trying to be really specific about what you’re doing. I get countless cold emails and cold calls where I have no idea what the product is. I even get a lot of direct mail, sometimes with really expensive stuff that’s been sent, and I open it up and have no idea what that company does. If I have no idea what they do, how is it supposed to help me?

The best tactic for anyone trying to sell to me would be literally to boil down how you’re going to help me in 2-3 words and make that the subject line. The best prospecting email I ever got came from a recruiter that I ended up using. This person had seen one of the roles that I was recruiting for on the website and sent me three anonymized resumes of people who fit that description. The recruiter was right on the money: I was spending a lot of time looking to fill that role, and she offered up three ideal candidates for me right there.”

Acceleration Insight

In each episode of the B2B Revenue Executive Experience, we ask our guests for one nugget of wisdom they would impart to a sales professional. Here’s this one:

“The number one thing is empathy. If you can’t feel the problems or pain in your prospect’s life, you’re going to find it difficult to figure out if what you’re offering helps them.

With that, some of the salespeople I’ve met will disqualify themselves. They’ll talk to someone, figure out what’s going on, then say, ‘Hey, my product can’t help you.’ Then sometimes they’ll give recommendations. The empathy is looking out for the other person rather than looking out for yourself because you want to hit your number.”

This post is based on a podcast interview with Alex Rosemblat from Datadog. To hear this episode, and many more like it, you can subscribe to the B2B Revenue Executive Experience.

If you don’t use iTunes, you can listen to every episode here.

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