The number 50 has taken me by surprise twice recently.
First, my 50th birthday snuck up on me, as it probably does most people. But let’s not dwell on that.
Almost equally as shocking was the realization that I’ve now done product marketing for 50 software companies. This includes about ten full-time jobs, over thirty paid consulting and freelance clients, and a handful of start-ups I’ve worked with pro bono.
I’ve always felt product marketing is something you have to learn by doing, not in the classroom. Don’t get me wrong, my academic pedigree is solid (I’ve always been good at studying a book and taking a test). But most of what I use as a product marketer I picked up on the job.
The absolute best lessons came from painful mistakes. There seems to be a parallel to playwriting here, of all things. David Mamet said in his MasterClass: “you cannot learn how to write drama without writing plays, putting it in front of an audience — and getting humiliated.”
Same’s true of product marketing.
Probably would’ve been a good product marketer.
So, after 50 companies, even more mistakes, and a few triumphs along the way, I think I may have learned a few things worth sharing.
Some people are more confident that I have things to share. I mentioned the “50” number to a client recently, whose response was “you should write a book!”
Meh, I don’t think so. But I figured I could at least start a blog.
So, this is the beginning of my blog. I’m calling it “View from the Hilltop.”
It’s both a word play on my company name, Flagg Hill Marketing (uncreatively named after a topographical feature of my neighborhood), and a metaphor for me sitting on a hill of 50 companies’ worth of experiences to draw from.
Another number is going to come into play here: 11.
I’ve boiled my lessons down to 11 key points, each of which will be its own blog post. Insert the obligatory Spinal Tap reference here — but that’s not why I picked 11. It just felt right.
It’s actually more like one overarching lesson and then ten topic-specific ones.

“This blog goes to 11.”
Here are 11 lessons I’ve learned from doing product marketing for 50 software companies:
- CEOs, not just CMOs, should care about product marketing
- The best product messaging isn’t about the product
- Pick the right market or the wrong one will pick you
- You only have one buyer persona that matters
- The right pricing always feels a little bit wrong
- When it comes to competitive positioning, less is more
- Sales enablement is transactional (surprise, surprise)
- Most marketers try to do each other’s job while doing their own badly
- Product should be the tail, not the dog, of product launches
- Funnel analysis can make the customer journey suck less
- The worst evangelist in the company should be the product marketer
In a meager attempt to be provocative, in this post I will simply submit the list without further comment. Other posts will explain each point.
The posts that are already written are linked from the list. If you’re interested in a topic not yet covered, get in touch or hop into one of my office hours.
Lastly, I can’t resist this sarcasm.
Would anyone ever actually set out to build wisdom in the field of product marketing?!
In thinking about that, I feel a little bit like Arnold’s dad in this scene from The Wonder Years.
“Dad, when did you decide you wanted
to become a [product marketer]?”
There are so many layers in the dad’s laugh in response to his son’s question. Replace the dad’s job title with “product marketer” (or most jobs) and it still works.
Nevertheless, it’s been a fun and interesting climb to the top of my little hill.