Looking back at my time at Datadog, I can honestly say it was a masterclass in misrepresentation and disappointment. What was promised to me during the recruitment process couldn't have been more different from the reality once I walked through the door. If you’ve ever had the joy of being told one thing, only to realize you’ve been led into a completely different world once you're in, you’ll understand my frustration. From management to culture, to the sales methodology that everyone claims is "the best in tech," it was nothing short of a Kafkaesque experience.
Recruitment: Lies, Damned Lies, and… More Lies
Let’s start with the recruitment process, which was about as transparent as a brick wall. I was sold the idea that promotions and internal moves happened regularly after just nine months. My recruiter, my manager, everybody told me this. "You’ll be on the fast track!" they said. Fast forward to me joining the company, only to learn that promotions are actually a two-year slog in the Commercial AE role before you're even eligible for a move. That little tidbit? Not mentioned once during the interview process. If I had a dollar for every time I was misled in the recruitment phase, I could have paid for parking at the office… which, by the way, isn't free. Surprise!
Now, onto the "flexible" hybrid work environment they touted. "People-first," they said. Well, turns out "hybrid" actually means, "you must show up at the office from 8:30 AM to 5:30 PM, no questions asked, and don’t even think about leaving a minute earlier." Need to leave for a doctor's appointment? Tough luck. That’s Tuesday or Friday territory—remote days, where you can "take care of yourself" while the rest of the team grinds away in the office. This sense of inflexibility? It’s truly a work of art. If flexibility had a thesaurus entry, this place would be the opposite.
And that OTE they promised—$160,000? Yeah, that’s adorable. In reality, hitting that target is a pipe dream for 75% of first-year Commercial AEs, if not more. So, while you're doing your best impression of a hamster in a wheel, chasing unattainable goals, remember that 25% of the sales team gets the glory. The rest? Well, they’re just living the dream of chasing something that isn’t going to happen.
Sales Methodology: The Art of Harassment
Let’s talk about this so-called "best sales methodology in tech." The pitch is all about MEDDIC, Command the Message, and the book A Qualified Sales Leader—which is apparently some sacred text. In theory, these methods are fine, and I’m sure they work for some companies. But at Datadog? They’re comically misapplied. Here, the focus isn’t on building relationships, understanding clients’ needs, or providing value. Oh no. At Datadog, the art of sales is less about finesse and more about bullying.
Your job as a sales rep is not to help clients solve problems but to harass them into meetings, force them into trials, and, if you're lucky, get them to sign up for services they have zero interest in. And don’t worry—your manager will always be there to encourage you to add products that the client doesn’t need just to hit a goal. Selling something a client won’t use or need? That’s just a fun little Monday morning activity. The product’s great, don't get me wrong, but the way it’s sold? Yikes.
If you’re not into pestering clients until they hate you, don’t worry—you're not alone. Most customers I interacted with already had a healthy disdain for Datadog before I even dialed their number. Why? Because every sales rep at Datadog seems to think that getting yelled at by a potential customer is a badge of honor. There's no art to this approach, just a whole lot of relentless pestering until someone finally breaks down out of sheer exhaustion.
And the management? Well, let's just say if you expect any actual coaching or development from them, you'll be sorely disappointed. Instead of guiding, mentoring, or developing a relationship with their team, the sales leadership at Datadog operates via Slack tirades. Messages like “KEEP PUSHING YOURSELF” are the equivalent of a motivational poster in a toxic workplace—empty, vapid, and ultimately demoralizing.
You want actual help with a deal? Prepare for the most dismissive answer possible. I once asked for help with moving a deal forward and the response was, “Have you ever used Salesforce before?” That, my friends, was my manager’s idea of being helpful. The real goal of leadership at Datadog seems to be to churn and burn employees as fast as possible. If you don’t succeed, fine. If you leave, fine. They’ll just plug another warm body into your seat.
Culture: Cliques, Micromanagement, and All the Drama
Now, let’s get to the "culture". Datadog would like to tell you that they have a culture. Well, they do… it's just the worst kind. The teams are divided into cliques, and good luck fitting in unless you’re fully dedicated to selling your soul to the company. The sellers have their own little world where ego and petty competition reign supreme. You get the vibe that even junior sellers, fresh out of college and with one deal under their belt, think they have the right to lecture you on your qualifications. Talk about weird.
And if you think management will support you, think again. There’s no rapport or camaraderie—managers make sure to stay above it all, talking amongst themselves while you do the actual work. You’re just a cog in their high-pressure sales machine, and they’ll remind you of it at every turn.
Office days are rigid, as in you have to be there from 8:30 AM to 5:30 PM—no exceptions. If you try to leave early, prepare for a public shaming. I witnessed someone get told to sit back down at their desk at 5:21 PM. The micromanagement is absurd. Need to sit in a common space or take a break? Nope. Get back to your desk, and keep dialing until you drop. No breaks, just relentless work.
And just when you think you’re free, on days when a regional VP visits, you’ll be required to come in on a day you’re not even scheduled to be in office. Will they let you leave early? Oh, of course not—only you, the employee, have to sacrifice your time. And if you’re unlucky enough to park in the Denver office, prepare to shell out $12-$16 a day. So, enjoy those free lunches they give you, because they're clearly just there to keep you chained to your desk with zero personal life.
One particular director in the Denver office, who’s praised for his “no-nonsense” approach, could only manage to instill fear and intimidation in his team. Rather than coaching or building positive relationships, he’d send out passive-aggressive Slack messages designed to make people feel like they were walking on eggshells. His idea of leadership was to belittle employees publicly while providing zero constructive feedback.
And forget about team events—if you're not into binge drinking, you're probably not going to fit in. After work, you’ll be expected to stay for events that, frankly, nobody wants to go to after already putting in 45+ hours a week. But hey, that's what the “culture” is all about, right? Sacrifice your personal life, your happiness, and your well-being for the company, because that’s what “being a team player” means at Datadog.
The Product: A Shiny Object in a Pile of Garbage
Here’s the most frustrating part: the Datadog product itself is excellent. I genuinely believe it’s a fantastic product with a ton of potential for clients. If only the company could get its act together and train their sales team to actually sell it with some integrity and professionalism. Instead, the aggressive and dishonest sales tactics only hurt the product’s reputation, meaning you’ll spend more time trying to undo the negative feelings customers already have about the company than actually selling the product.
Conclusion: A Career Regret, Not a Learning Experience
In conclusion, Datadog was a huge disappointment. If you’re considering joining, I highly recommend you take a closer look at what’s actually going on behind the shiny recruitment pitches. The sales methodology might look good on paper, but in practice, it’s just harassment. The culture is toxic, and the inflexible office policies make you feel like you’re trapped in a cage. And the fact that I was promised a great career trajectory, only to find out I was stuck for two years in a role that didn’t align with my goals, just makes me feel downright stupid for ever buying into it.
If I could go back, I would’ve run the other direction. This experience was a rude awakening that there’s a lot more to a company than a flashy product and an impressive job title. Do yourself a favor and avoid this mess.
