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.