Pre-IPO companies have a special energy. There's an urgency, a scrappiness, and a willingness to try things that often gets lost once the IPO paperwork is filed. From 2014 to 2017, I had the privilege of working at Square during exactly this phase, when we were big enough to matter but small enough to move fast.
Those years shaped how I think about product marketing in ways I'm still unpacking. We launched Cash App, multiple hardware products, and expanded into international markets. Some initiatives succeeded spectacularly. Others failed quietly. But three principles emerged from those experiences that I still carry with me today.
Jump In
At Square, there was no luxury of waiting for perfect conditions or complete information. When a launch was coming, you didn't ask "Is this ready?" You asked "What needs to happen to make this work?"
I remember being pulled into hardware launches where I was learning about NFC readers and EMV compliance in real-time. The expectation wasn't that I'd be an expert. It was that I'd figure it out fast enough to be useful.
This "jump in" mentality creates product marketers who are adaptable rather than specialists. You learn to:
Get comfortable with ambiguity and incomplete information
Ask the right questions quickly to close knowledge gaps
Build credibility through action, not just expertise
Recognize patterns across different product types
The traditional approach to product marketing often involves deep preparation before execution. Pre-IPO environments don't afford that luxury. You learn by doing, and you learn fast.
Fail Fast
Square's culture didn't just tolerate failure. It expected it as part of the process. The key was failing quickly enough to course-correct before it became expensive.
We launched features that didn't resonate. We tried messaging that fell flat. We built enablement materials that sales teams didn't use. But because we were moving fast, we could identify what wasn't working within days or weeks, not months.
This principle manifests in several practical ways:
Ship minimum viable marketing alongside minimum viable products
Test positioning with small customer cohorts before broad launches
Build feedback loops that surface issues immediately
Don't over-invest in perfecting materials before validation
The hardest part isn't accepting failure. It's building the discipline to recognize it quickly and pivot. Too many product marketers (myself included) fall in love with their messaging or their launch plan and defend it past the point where data shows it's not working.
Ask Questions
In a pre-IPO environment moving at breakneck speed, the people who succeeded weren't the ones who looked smart in meetings. They were the ones who asked questions that led to better decisions.
I learned that there are no stupid questions when you're trying to understand:
Why customers behave the way they do
How pricing models need to evolve for new markets
What competitors are doing that we're not seeing yet
Whether our positioning actually resonates
The best product marketers I worked with at Square were relentlessly curious. They asked "why" until they understood not just what was happening, but the underlying mechanics. They challenged assumptions, even their own.
This meant:
Questioning whether our target customer was actually who we thought it was
Pushing back on product decisions that created messaging challenges
Admitting when you don't understand something rather than pretending
Seeking out people who have the context you lack
Why These Lessons Still Matter
You don't need to work at a pre-IPO company to apply these principles. Whether you're at an enterprise SaaS company, a startup, or an established brand, these lessons translate:
Jump in when there's ambiguity rather than waiting for someone to define your role perfectly.
Fail fast by testing your assumptions early and often, rather than building elaborate plans before validation.
Ask questions that challenge conventional thinking and uncover blind spots.
The pre-IPO mindset isn't about chaos. It's about bias toward action, learning from reality rather than planning documents, and building organizations that can adapt faster than their competitors.
Looking back, some of the most valuable lessons came not from our successes, but from how we handled the inevitable failures and pivots. The question isn't whether you'll face uncertainty and setbacks. The question is whether you've built the habits to navigate them effectively.