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Chief
It’s a lot less about questions and more about listening to their stories, understanding their culture & values and assessing if you’ll enjoy working there. Be ready to share about yourself too.
It’s an opportunity to start building relationships with your (potential) future colleagues.
Pro
PE's plan would be first thing in my mind. PEs typically invest and hardcore cut all the fat and get cash flow positive as quick as possible. Then they look to sell in 3-5 years.
Downside is WLB might not be great since you're ultimately reporting to your new PE overlords and when they sell a lot of jobs will likely be cut.
Upside is you will probably be impactful in your role and have significant autonomy. I've seen some PE ops consultants churn and burn at different portfolio companies, making a name for themselves as a great turnaround consultant. CFO/COO roles over and over again.
My honest opinion: don't take these roles.
First question is what is any upside to this offer. You are already making near the top end of their range, and the job will likely be more painful given the startup and private equity scenarios. What are you leaving out or don’t know about that would make this worth considering?