I applied through a recruiter. The process took 1 week. I interviewed at Datadog (Boston, MA) in Sep 2017
Interview
20 minute phone screen with a rep from Datadog Talent, followed by 2 hour in-person interview with four different sales managers. First guy is the hype man, talks talks talks about Datadog. Next guy was very metered and quiet-- he asked questions about specific items on your resume, but noting too wild. Third guy seemed to not anticipate having to interview me. Fourth guy was the one I would be working for-- he had his ducks in a row, took notes on his computer, and asked the most clarifying questions about your sales process. He also attempts to close you/get you to say "YES I WANT TO WORK AT DATADOG" before you leave their offices.
Interview questions [1]
Question 1
Why Datadog?
What are your metrics/targets in your current sales role?
What strategies do you employ when prospecting?
My interview experience was a complete waste of time. The recruiter simply talked at me, rhyming off what felt like an autopilot script, with very little effort to actually listen to anything I was saying.
After that, the process was nothing but automated email triggers from their ATS. Nobody checked in, nobody made sure I understood the next steps, and nobody seemed remotely interested in whether I was happy with the process. It felt like I was just a number and that the focus was more on hitting interview scheduling quotas than actually assessing candidates properly.
To finish it off, I received an automated rejection email with zero feedback. If they genuinely want to attract strong AEs into the organisation, they should seriously revise this process.
I applied through other source. I interviewed at Datadog (Boston, MA) in Jan 2026
Interview
3 phone calls, one hour long in person interview, 1 hour long zoom call. Such a waste of time, especially having to take off of work in order to interview with them. Seems like they definitely string you along and make the interview process as long as possible.
Professional process and helpful recruiter. They will provide you some materials to prepare. But during interview, the co-interviewer was quite rude. Giving pressure to candidate and even showed disrespectful. Main interviewer was good tho.
Interview questions [1]
Question 1
experience, role play including cold email and in-person meeting.