My ClickUp Interview Experience

Dec 15, 2022
4 min

In How I Wasted 6 Months Creating Disgo, I highlighted my failure to acquire a job due to my suboptimal LeetCode performance or failure by the interviewer to recognize a valid solution. Well, I haven’t practiced for shit since then. Regardless, I did another interview loop with ClickUp in November 2022.

Here is how that went.

The Phone Interview

I applied for a Junior Engineering role for DevOps and a Senior Engineering role for API Integrations. The Technical Recruiter, Ryan Sand, is a cool person who told me about the company and how it raised $400 million in a Series C. I was asked questions about my experience in Software Development and moved into the Senior Engineering API Integrations interview loop.

The Technical Interview

The technical interview was with Hiring Manager James Bilous of the data modeling team. We spent ~15 minutes talking about our experience, then started the Data Structures and Algorithms LeetCode interview.

The question — which I had never seen before — instructed you to find pairs within an array of numbers that added up to a given sum; where an index cannot be used twice. This question was either a LeetCode easy or medium, given that I solved it in less than 20 minutes.

PogU Pass

After this exercise, we spent up to 10 minutes discussing the company and how they are attempting to switch to polyrepo microservices. Unfortunately, it’s not going so smoothly (lmao).

Lucky for them, I have experience with microservices, given my heavy usage of Go. We also discussed the Krazam Microservices video, and James told me that I definitely would be moving to the next round.

The call lasted 43 minutes; ended with 17 minutes left.

The Onsite Interview

Hey Caleb,

Thanks so much for spending your time with us during your initial interview. We really enjoyed getting to know you!

I was able to follow up with the team for some updates, and while they were super impressed with your skill set and appreciate the time you put into meeting with us, they’ve ultimately decided to move forward with other candidates in the process at this time who have more experience.

While I know this isn’t the best news, I want to reiterate that our team really enjoyed your conversation and would love to keep in touch as we continue to expand our team. Should any other positions come up that would be a fit, I will be sure to reach out right away. Feel free to add me on LinkedIn and don’t hesitate to reach out if there’s anything I can help with!


No, I don’t believe these people are “super impressed”. I don’t have a LinkedIn. I will work to gain more recognition.

What Happened?

At this point, I have no clue.

  • The hiring manager told me I was moving forward.
  • I passed the coding assignment in O(N) with comments within 25 minutes.
  • I understand the team’s entire stack (NodeJS, Monolith transition to Microservices) and have worked with the container (Docker) and container orchestration beyond Amazon EKS (Managed Kubernetes).
  • I am engaged in work involving distributed systems and concurrency.

I was rejected due to “experience”.


I will give ClickUp props for having a faster interview loop than other companies. The Recruitment Coordinator (Isabella Munoz) was friendly and enthusiastic. But companies aren’t your friends... It’s nothing personal.

Here are some additional notes about this interview loop.

  • The email indicating that I passed to the technical round used the wrong name (Brooke) to address my phone interviewer.
  • During the discussion about my experience in my technical interview, I focused a lot on my recent Go projects. In hindsight, it may have served me better to focus on my work with APIs in NodeJS (Audius Enhanced) since that seemed to be their focus. For example, I was asked how the JavaScript Event Loop and async syntax worked.
  • During the technical assessment, I asked James whether I should submit the code, but he said, “No, I can do it myself later.” I’m not sure what the implications of this decision were, especially given the plot twist in my expectations to move on to the next round.

One must assume that James or the next hiring manager changed their mind when they found someone with a more traditional path.

Going Forward

I am confused since I did everything “correctly”. 

At this point, I seem to be consistently failing at impressing the “Hiring Manager” instead of failing technical rounds. So I would like to view the resume and performance of the person that acquired the role I applied for. This is the third company that has been “super impressed” with my skills but passed me over due to “experience”. Obviously, I’m lacking somewhere…

Before you ask, the answer is yes. I have more stars than them on GitHub.

I believe that a recent resume update is the cause of my recent Hiring Manager rejections. Since the last set of interview loops, I changed the layout of my resume by placing “work experience” before projects. When I did this, I experienced a regression in my average interview timeline. So, I must swap these sections — experience and projects — back since employers do not seem to recognize paid experience from self-employed work.

Consider that my failures to enter Roblox and Amazon were the result of poor performance during a single round in one of the final interviews, while these recent rejections have been the result of the Hiring Manager's consideration. So my resume needs to be more "impressive" than other candidates (who exaggerate their skills).

I will also remove the “Education” section from the resume so my age cannot be gauged since too many people ask questions about this in higher-level interview loops.

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