Video chat with CEO, team dinner with CEO and founding team, 1-1 with CEO. CEO showed up to video screening interview looking like a rapper, wearing a baseball cap sideways. Felt like I was bro-ing out at a bar more than interviewing for an exec role. Made it to a dinner with the whole team, the first place we went to was booked because they hadn't gotten reservations. Had a decent dinner with the team members. Disagreed with CEO about basic product questions. He seemed offended when I told him that I was unable to complete the main signup flow from the homepage. And when I pointed out glaring typos on the website, arguing that this affects credibility, he strongly argued that none of that mattered "because I know my customers" Things he told me: "I'm not sure if product sense exists" The company claims to value a feedback culture, but when I offered some feedback the CEO invalidated it and became hostile. This is for a Head of Product position, so you'd assume they want to hire someone with a strong vision to lead product. Instead it felt like they just wanted to hire a yes man. Overall the CEO showed a lack of respect and attention to detail through the entire process. Or maybe I'm just not enough of a consulting bro to appreciate the culture. The CEO is obviously plenty smart, but could benefit from some leadership training to help tone down the raging narcissism.

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.