I applied through a recruiter.

There were five sessions with several different people in the company:

• Coding and problem solving: JavaScript coding challenges focused on asynchronous code, promises, and other JavaScript trivia.
• Project deep dive: A chat about a project I have worked on, architectural decisions taken, code organization, interesting problems solved, issues faced, and more.
• Behavioral interview: A conversation about my approach to juggling competing priorities, managing conflict, dealing with ambiguity, and similar behavioral questions.
• Software design coding challenge: A challenge with vague requirements designed to focus on the handling of edge cases.
• Product demo showcase: A showcase of the product.

I was impressed with the product and thought it was very cool, and I would have been very excited to be part of the team from that point of view. I found the interview process challenging but pleasant overall, as everyone was very personable and friendly. This was one of my first interviews in my current round of job-seeking, and while I did well on the technical skills side and had a good culture fit, I ultimately did not get the position due to a perceived lack of leadership experience necessary for this particular role.

A couple of red flags from my point of view:

• I thought it was unusual for the CTO to still be deep in the weeds of coding work, but I guess it is his baby, so it's hard to blame him. I've heard stories from other startups that this kind of setup can lead to a less-than-stellar experience for newly onboarded engineers who want to contribute to such a codebase.
• The company appeared to be somewhat top-heavy with lots of team leads, managers, directors, and a mountain of new feature requests and work to do, and few individual contributors actually writing code. Perhaps this recent or current hiring spree alleviates some of this imbalance.

I generally see myself as a person who focuses on the product, code, and customer satisfaction while trying to avoid wasting time on politics and meetings, and I think this may have been an area where I would not have been a great cultural fit. I was very upset when I initially received the news of the rejection, but shortly after this interview I found a similar role at a much larger, more established company, which is ultimately a better fit for me. I am thankful to all the folks at the company for speaking with me, and it was one of my more pleasant interview experiences of this go-around.

How would you handle an ambiguous feature request with the added pressure of a short deadline?