I applied online. The process took 4 weeks. I interviewed at Flexport (San Francisco, CA) in May 2015
Interview
The first round was a skype interview and unfortunately that morning my computer decided it didn’t want to live anymore. But the person interviewing me was totally understanding and suggested we facetime as an alternative. The interviewer asked some challenging questions to gauge my interest in the company/industry/position - I had no experience in the industry but my answers were genuine, and I felt the interviewer appreciated that.
Second round was in the Flexport office (which is awesome). I did have to sit in the lobby for a few minutes, but since its an open office you can plainly see that everyone is extremely busy. I met with three people total: The first worked in operations, the second was the head of business development, and the third was the COO. The questions were mostly behavioral/fit, experience-oriented, and one theoretical case study. Overall it was a positive experience and everyone was very excited about the future of the company.
Last round was a meeting with Ryan, the CEO. When I got into the office they were eating lunch so my interview took place while me and the CEO ate pizza. It was just a casual conversation, and by that point I had done enough research to have a decent conversation about the industry, competitors, and future of the company. A week later I got my offer.
The industry space is really exciting and Flexport has HUGE potential so I already loved the value prop – but the employees sold me on the company.
I applied online. The process took 3 weeks. I interviewed at Flexport (London, England)
Interview
I had to go through a 'panel' interview and instead of speaking to two or three people at once, I had to have a video call with 4 different people over 5 sessions. If you are working full time, especially if it's full time in the office, this is absolutely ludicrous to demand this much time off from people to go to these interviews.
Interview questions [1]
Question 1
How do you handle conflict within a team? What do you do if a colleague is not 'pulling their weight'?
I applied online. The process took 1 week. I interviewed at Flexport (Chicago, IL) in Nov 2025
Interview
The interview went very well. It was a positive and remarkably straightforward discussion, creating a wonderfully friendly environment. I appreciated the clear questions and the honest, direct feedback provided throughout the entire engaging conversation.
Interview questions [1]
Question 1
Tell me about yourself and walk me through your resume.
Describe a time you faced a significant challenge at work. How did you handle it, and what was the outcome?
Why do you want to work for our company, and why are you interested in this specific role?
It was great! Everyone was very nice and friendly. Everyone I talked to was helpful and they answered any questions I had. Although I did not get the job they were still very clear and forthcoming about it.