CEO reached out via LinkedIn and the assistant scheduled a call a few days later. The CEO called and was asking questions as if the role was for a job for a brand new grad: walk me through your resume, why are you interested in us (ummm, you approached me), describe a product that you have used that creates an attachment to you (technical or non-technical). The interview seemed very disjoint as if the CEO was asking questions off of a checklist rather than having a conversation with me and weaving what he was looking for into the conversation. When I started asking questions he seemed like he didn't want to answer or didn't have any good answers. 1) What is your value prop? "I founded the company because I had a hard time getting insurance and others have the same problem. No one can help them better than we can." 2) What are you biggest challenges? "We need to grow." Why? "Because we need to get bigger." Why? "Because it's about getting bigger, that's just what you do." 3) What are your biggest product challenges? (I essentially asked the same question again multiple times to figure out what they needed). "We need to grow the top of the funnel and convert more leads." What is the problem now with it? "We need to grow fast." 4) Why are you looking for this role now? Who is fulfilling this function right now? "I am. We need to grow so we need someone." It seemed the strategy was just growth. I don't know if that was a demand from investors or a lack of management experience but based on the answers to the questions I asked, it seemed like the latter. I asked about the process and was told that I should hear back in a few days. It's been 3 weeks but I haven't heard anything.

I was connected to their CEO via AngelList. Their recruiting coordinator reached out and asked me what times I would be available. I sent over a handful of times, but didn't get a response until at the very end of my availability. When we finally scheduled the initial call with the CEO, the CEO never showed up. I contacted the recruiting coordinator and she explained she forgot to add it into his calendar. When I finally spoke with the CEO, he came across cold and disinterested. He didn't seem particularly interested in me as a candidate, and just listed of your typical questions (e.g. why our company, how do you prioritize a roadmap, describe a non-technical product you love and how do you apply its product principles to product a technical product). When I had time to ask him questions, his responses were very short, lacking details, and he sounded arrogant. When I asked him about the process and next steps, he mentioned that now that I've spoken to two people in the company (which I hadn't - he was the first person I was speaking to), they would bring me in for an on-site next week. When they reached out to schedule me for an on-site, I explained how I wasn't local to SF but I'd be happy to come down if they were to cover my costs. This was something they never bothered to confirm or check in the first phone call. At this point, I felt frustrated in the process and decided to withdraw my candidacy.