GumRoad interview questions

Had a chat with Sahil about Gumroad's engineering culture and remote/asynchronous work philosophy. No technical component, usually they assess verbally if you can handle the challenge, then do a trial period.

I applied in January 2023. The Gumroad Jobs page described a process that started with a homework challenge that had to be completed in less than 8 hours with the same stack as Gumroad. Over the next 3 days I completed it in my spare time, and stopped just before the 8-hour mark. When I was ready to submit I went to the Jobs page and the page had been rewritten and the process for this position had completely changed! This time it had to start with an email to the CEO listing accomplishments. So I sent the email as described and mentioned that I hoped that my completed challenge would be accepted in lieu of the new one mentioned in the new job description, which didn't state what the new challenge was about anymore. Since I hosted my completed challenge, I saw the server log hit coming from Sahil, the Gumroad CEO, when he visited it. I also saw in the telemetry that he didn't use the tool I'd built at all. I shrugged it off assuming that he might have decided to install it from source (since I provided a Github link) and tried it out locally this way. Although it's much more likely that he didn't try it at all. Less than 20 minutes after the server log hit I received an email from Sahil (CEO) stating that "a call would be great". No answer to my question about whether my challenge would do, as I hoped I wouldn't be expected to complete a second, different one. The call happened a few days later and felt very positive. However Sahil barely had any questions to ask me. I had to drive the conversation myself when talking about my own experience, unsure what he'd like to hear about. I asked him a bunch of questions about Gumroad and he talked a lot about that. It was a nice and interesting chat, but having interviewed a lot of engineers myself, I failed to see what I'd be assessed on. He ended the conversation stating that I'd hear back the following week. I let 8 days pass and in the meantime checked the Gumroad Jobs page which, as you might guess... Sahil completely rewrote again. This time a new, longer detailed challenge was described. At that point it was the 4th major update to the hiring process in less than 2 weeks since I first saw the posting. It really felt like I was a beta tester of his unfinished draft hiring process... and honestly I wouldn't be surprised if it's completely scraped and overhauled again a few days from now. Having waited 8 days and getting near the end of the following week, I asked for an update. That's when I was rejected with a one-liner. I could go on about how I'm overqualified for that job. I was mostly interested in it because I'd like to work part time. But that's kind of besides the point. This behaviour is an enormous red flag for a small organization. Having experienced a CEO like this before, I have no doubt that this is also his management style on a day-to-day basis, constantly changing direction and requirements as staff have already started working on the previous ones. As a job applicant, it should be obvious that a Gumroad hiring process with a challenge requirement: - is highly likely to change without notice - might required hours of work and won't even get tried or properly reviewed - it's a roll of the dice if you'll get any response at all - if you get an interview, it will feel completely unprepared and amateurish