Andrew Penny, October 7 2025

Most Go To Market Problems Don’t Start in Sales and Marketing

They lie much deeper

 

I taught skiing on weekends for almost 40 years and one of the most powerful skills I developed was what is called ‘Detection and Correction”.  It’s the skill of identifying the symptom and then determining the root cause.  

Inexperienced instructors can spot the symptom—but rarely identify the root cause. A student may be skiing without flexing their knees – ‘bend your knees’ is the recommendation. Unfortunately, that’s almost always a shadow of the real issue. Typically, it’s  a much deeper issue such as poor balance driven by fear. “Bend your knees” is a useless piece of advice. 

In business, CEOs often come to me with similar requests: “We need to improve our go-to-market activities. The messaging isn’t landing. The funnel’s underperforming. We have lots of meetings but no sales. We’re not sure this segment is right.” 

But once we start pulling the thread, it usually leads somewhere else entirely. 

Not to sales. Not to marketing. But upstream - into the strategic layer of the business. That’s where the real issue often lives. 

Most go-to-market problems don’t originate in go-to-market. They’re just expressed there. The deeper source is almost always a lack of clarity: around positioning, around priorities, or around how the company actually creates value. 

I’ve seen messaging struggles that were really strategy struggles; trying to serve three different customers with one undifferentiated story. I’ve seen low conversion rates that weren’t about sales execution, but about unclear ICP focus and internal misalignment. I’ve seen GTM teams “underperforming” when the actual issue was structural - instead, the comp plan didn’t match the motion, or the product wasn’t ready for the segment being targeted, or the distribution channels were misaligned. 

In each case, the execution looks messy. But the thinking behind it is what is actually broken. It’s understandable. Most founders and CEOs are under pressure to grow, to get to market fast, to prove traction. And they’re often too close to the product - or too buried in the day-to-day - to step back and ask some of the foundational questions. 

Questions like:


These aren’t theoretical questions. They have direct implications on what you build, who you sell to, and how you scale. 

When companies take the time to answer them clearly:

When they don’t, growth becomes effortful:

 In my experience, the best go-to-market work doesn’t start with better copy or smarter plays – those are just shadows. It starts with clearing the fog. Helping the leadership team see the business more clearly. So the right bets can be made with confidence and coherence. 

GTM doesn’t fail at the surface. It breaks at the source.   


See you next time, 

Andrew

Written by

Andrew Penny

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