Extensive interview process. Pretty comprehensive and varying levels of preparedness by interviewers. Most interviewers were late, which was pretty disappointing but on the whole it was a positive interview experience.
Lengthy interview process took place over nearly two months, with 6 rounds in total, covering a broad range of technical and non-technical topics with a take home coding test and an in-person system design interview. At all stages it felt like they were really drilling deep on what my specific contribution to each project I'd worked on was, including how I used data to back up any decisions. The take home coding test took a while, and then I didn't actually get many questions about it but I think it's because I'd covered off most of what they might ask about.
I received very detailed feedback which was really appreciated, and the hiring manager was very communicative. I had a mix of positive and negative feedback, with some of the negative feedback from one of the in-person interviews seeming slightly harsh and at odds with how I felt the interview went, but for the most part it was fair.
I felt the process was too long and I was stalling other offers whilst waiting for my last round.
Overall the interview process was very in-depth and I definitely got the feeling Checkout have high expectations for the Staff Engineer role, so I'd recommend good preparation, especially around being able to explain the details of previous projects.
Interview questions [1]
Question 1
Design a payment gateway - covering observability, scalability, functional/non-functional requirements, technology stack, design choices (eg, synchronous vs async)
Interview with Data Analytics Team Hiring Manager : Interview Stage 1 – Context & Team Framing:
The interviewer walked through how the analytics team operates, what it does vs. doesn’t own, and how data supports commercial, merchant, and operations teams, assessing your ability to absorb complexity, handle ambiguity, and think in business narratives rather than dashboards.
Stage 2 – Data Philosophy & Operating Model:
They emphasized an internal-consulting mindset (“we give the kitchen, not every plate”), executive storytelling, recurring leadership reporting, and self-serve analytics, testing cultural alignment, seniority, and comfort with shared ownership rather than end-to-end control.
Stage 3 – Scope & Problem Complexity:
By describing cross-system inconsistencies, data quality issues, and evolving strategies, they evaluated whether you can operate in messy real-world data environments and think in terms of frameworks and long-term remediation instead of quick fixes.
Interview questions [1]
Question 1
Do you understand the difference between analytics, data engineering, and operations?
Do you understand that this team focuses on ideation, metrics, and storytelling, not pipeline scaling?