Datadog was by far the worst professional experience of my career, and I still have PTSD from the level of toxicity and misery that is rampant here.
Management is toxic and lazy — there’s no training, no real support, and it's blatantly clear they do not care about you or your growth. You're a number and at best, you'll experience micromanagement. Keep in mind that you will be encouraged to be "proactive" in your one on one's about "areas you'd like to grow" - this is not for coaching but a trap that will be used against you to demonstrate where you fall short even though it didn't come from management.
You’ll be hounded about unrealistic KPI's but not given the proper tools or coaching to succeed. 95% of the role is aggressively outbounding a completely burned book of business with the most lack luster tools you can imagine (ie, they just got a tool to provide phone numbers - before, reps would pay ~$50/mo just to have access to a site to get phone numbers to prospect into).
You’re expected to call 80+ people (from different numbers until someone answers I might add) and write them highly personalized emails (which will be criticized) - this is the minimum requirement for daily "supplementary" activity. Your schedule will constantly be interrupted with "Call Days" and disqualified accounts are recycled to another rep a week later - these toxic sales practices are why prospects hate you as soon as you say "Datadog".
Hitting quota consistently is extremely rare (for context, the sales org has a few hundred reps and less than 40 hit their annual number across all verticals last year). Most reps don’t make it past 6-9 months, many get PIP’d during their ramp period, and you're considered a veteran if you stay longer than a year.
The company promotes a “new logo bonus” for $500 deals (which only a handful of reps hit) but leaves out that reps will have to pay back these bonuses if usage doesn’t stick — some owe thousands back to the company.
The culture is not only high-pressure, it’s unhealthy and demoralizing. There’s an unspoken expectation to stay late (despite working 10hr days already), show up early, come in 5x a week every time it's the EOQ and hang out at the downstairs bar after work if you want inbound leads or favor. Mental health struggles are rampant, and the bathrooms/downstairs offices are known places to go and cry from the stress. There are many reps who end up relying on stimulants/downers just to cope. “Unlimited PTO” is meaningless — you’ll be judged and lectured for using it.
You’ll also be out ~$200/month for parking with no reimbursement, and company trips don’t cover basic expenses like food.
Bottom line: Datadog might look shiny from the outside, but the culture is rotten. Read the reviews. Believe them. No job is worth sacrificing your wellbeing, and anyone considering Datadog deserves far better.
