I applied through a recruiter. The process took 8 weeks. I interviewed at Datadog in Jun 2025
Interview
This was the best interview experience in my 15 year career.
The overall process took a bit less than 2 months for me and involved the following interviews and stages.
Stage 1 - contact/interview with a recruiter
Stage 2 - interview with the hiring manager
Stage 3 - 5 interviews to check the skills: technical background interview, project management interview, people management interview, coding interview and system design interview.
Stage 4 - offer
The process is long and does require significant involvement from the candidate. However what really stands out in this process is that you have a technical recruiter that steps in at stage 3. They really help you prepare efficiently for the technical interviews by setting clear expectations for each round, sharing feedback and coaching/cheering you.
Regarding the interviewers, everyone was great. They all created a positive environment, asked questions in line with the expectations and allowed some time for me to ask questions as well. It's clear that they all followed quality interviewer training.
Congrats to everyone involved.
Interview questions [1]
Question 1
For the system design interview: design a pixel war website for 100k users.
I applied through a recruiter. I interviewed at Datadog
Interview
Datadog has a very in depth interview process covering basically everything you would expect (coding, design, delivery management, people management, etc). They provide plenty of documents for preparation and a rough outline of what each interview entails to really give you the best chance of success and it's up to you to make the most of that. I wouldn't say any particular interview is difficult, but it's a lot of interviews covering a lot of topics.
At the conclusion of the process, they provide not just a boilerplate "we had many qualified candidates but unfortunately..." email, but the recruiter will actually hop on a call with you and go through high-level feedback from each individual interview, which set me up very well for future interviews with other companies.
In my case, I didn't make the cut because I didn't go into enough low-level details in the technical interviews. They would rather hire people who have 10/10 knowledge in some areas and 5/10 in other areas than people with 7-8/10 knowledge across the board, so go into their interviews knowing that it's okay to hand wave some details of your designs as long as you can be very detailed in other areas.
I had a call with a Director of Eng. He seemed to be focused on something else and was seemed disinterested in being there. The feedback he gave was that I was too junior for an M1 role.
Interview questions [1]
Question 1
Tell me about an experience coaching someone on your team
I applied online. The process took 4 weeks. I interviewed at Datadog (New York, NY)
Interview
Great experience, recruiter was transparent and helpful throughout the whole process. I was not caught off guard at all during the rounds. Final Round was one hour each of:
- coding
- systems design
- overview of a project that I had overseen
- capacity management
- people management
I have a ton of respect for this company, everyone that I spoke with was humble and seemed to really enjoy working there.
Interview questions [1]
Question 1
The system design question is very data processing specific, like design a high throughput pipeline etc. Think about scale, fault tolerance, SLAs etc.