SimplyInsured Product Manager Interview Questions
& Process

So the interview process had three steps: first a recruiter screen, then a hiring manager screen which was actually the CEO for this role, and then a three-hour panel with various people, ending again with the CEO. The recruiter was really nice, explained the job, and it was a good chat. But after that, things got a bit weird. The CEO was munching on something during my interview (they say keep cams off to avoid bias, but still), and it felt like he wasn't really listening to me. He mostly just said 'that makes sense' and didn't really talk about how we'd work together. The three-hour panel was better, the engineering manager, another senior PM, and two engineers were great to talk to. We discussed working with data, company culture, and some PM behavioral and hypothetical stuff. Then the CEO came back for the final part. He mentioned his interviews can be 30 minutes or a full hour, 'no worries.' He then asked me to go through the website and suggest how to sell more to bigger companies, which felt a bit off for an integrations role. He finished by asking about my favorite app and favorite hardware. I was really expecting more about work styles and collaboration, but he kept saying 'that makes sense' while looking at his other screen. When I asked about feedback from the CS team, he basically trashed them, saying he didn't trust them or their info. The people I met otherwise seem awesome, and the recruiter was great, but like others have said, reporting to the CEO seems like a mess.

It was okay, they asked a lot of questions about my resume, but the questions from the interviewers started to repeat and it felt like they weren't really listening.

The CEO reached out on LinkedIn and my assistant set up a call. The CEO asked basic questions like walk me through your resume, why you're interested in us, and to describe a product you like. It felt like he was reading from a checklist and not having a real conversation. When I asked questions, he seemed hesitant to answer. He mentioned the company was founded because of issues with insurance and that their main challenge is growth, though his reasoning was vague. When asked about product challenges, he said they need to grow the top of the funnel and convert more leads, but again, the reasoning was just about needing to grow fast. He said he's currently handling the role and needs someone because they need to grow. It seemed like the only strategy was growth, maybe due to investors or lack of experience. I was told I'd hear back in a few days about the next steps, but it's been 3 weeks with no word.