AMA: Zendesk Senior Director Product Marketing, Josh Bean on Developing Your Product Marketing Career

I'm on my 5th year of product marketing in my career, with another 5 years before that in general demand gen at very small companies. I've had management experience in the past, but not in a Product Marketing role. Often times in smaller companies, there will be 1 or 2 PMMs, usually in a very flat hierarchy, or a single boss, with no room to really move up a proverbial ladder and into management experience. So what are ways that I can prepare myself now, so that if the time comes to apply for a Director position (either internally or at another company) that I can be considered even without recent people management experience? Are there any courses for this that are highly regarded in the management arena?

For example, a senior manager PMM title at a small company may hold the same responsibilities of a manager or lead PMM title at a large enterprise. I've heard many in my network worried to take a "dip in title" when moving in fear that it will hurt their resume progression. I'm interested to hear your take on it!

I had been managing a large organisation with over 4500 ppl, and nowadays I would like to shift my career to product marketing, and without owning the title previously i don't have courage to even apply a pm position. What road should i take to feel that i am ready?

I get a lot of critical feedback from my boss and I don't always know what to do with it or how to improve. Sometimes I don't even agree with the feedback.