I applied online. I interviewed at SimplyInsured in May 2026
Interview
Reporting directly to a CEO is a bad idea. Especially when you have another PM that reports to a CEO. Very unclear lines of who’s building what and why. Chief People Officer failed to make a very strong pitch as to why this a good place to work. Failed to say anything other than “this is a great business opportunity and we have a great culture” — which everyone says. At the end of the day, what really makes this place unique? Unclear.
I applied online. I interviewed at SimplyInsured in Feb 2026
Interview
The interview process contains three steps: recruiter screen, hiring manager screen (in my case the CEO), and then a three hour panel of individuals with the last person being the hiring manager (the CEO for this role).
The recruiter was great to talk to, explained the role, and was generally a positive experience. However, after her is where things began to fall apart a bit. The CEO was audibly eating something during my interview (they tell us to keep cams off to make sure there is no bias), and you could tell that whatever you said was kind of in one ear and out the other. His most common response was "that makes sense" and there was little to no discussion on how you would work together.
The three hour panel wasn't bad, the engineering manager, other sr pm, and two engineers I met with were really good to talk to. One went into how you work with data, one was culture interview, and one was more PM related behavioral and hypothetical questions; all people were great to talk to.
Then comes the CEO again, when the final interview came; he gave a preface that sometimes his interviews last 30 min, some last the full hour but "not to worry." Then he asked to go through the website and ask how you would sell more to larger businesses which seemed outside of the scope of the integrations focused role and then he ended with "what is your favorite app?" and "what is your favorite hardware product?". At this point I was again expecting more questions on work styles and how it would be to work with one another; but the entire time his main responses were "that makes sense" while viewing his other screen.
When I asked him about feedback loops with his CS team; he went on to put down the team saying he didnt trust them or the information given by them.
Overall; the people that work there seem great and the recruiter was great; but like all of the other reviews I think reporting to the CEO is kind of a mess and not something I would want to do or enjoy.
Interview questions [1]
Question 1
How would you optimize our website to sell to larger small businesses?
Seemed like it would be a quick process - HR conversation, CEO conversation because you report to him, and then a panel which includes the CEO again. The interview is easy - either you say something the CEO likes or you don't and don't ask any real questions to figure out what you will truly be doing. You'll be a Business Analyst (waterfall, not data) which is fine if that's what you do, not fine it's a true product person and definitely not if you're a Product Leader. Doesn't seem like you will drive strategy, you will execute someone else's strategy with limited input.
Interview questions [1]
Question 1
Simple and standard product questions which weren't the problem, I was very disappointed with how questions you ask were met.
Thank you for taking the time to share your candid thoughts on the role alignment and experience with our team. We apologize that it was not a positive experience for you, and take your feedback seriously in order to help improve our hiring processes. Best of luck in your search and in finding an opportunity that is the right fit for what you are looking for!
Sincerely,
SimplyInsured People Ops Team
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