I was speaking with a founder the other day, unpacking the the intricacies of his growing business. In a time where "good enough" is recognized as a necessary evil for growing businesses, his choice of word, sufficient, struck a chord. It was a reflection not of contentment or pride but of an underlying apprehension about the quality of his team's content. As I do for all of my Partners, I offered to review his website and content. 

Meanwhile, the founder's aspirations to scale his business upmarket was a firm contradiction to his admission. The content, he implied, wasn't compelling, spellbinding, or captivating. Don’t get me wrong—the content was fine. Yet, within the same breath, he spoke of lofty ambitions. This paradox left me pondering: 

The situation harkened to an image of a mountain climber poised at the base of a daunting peak. Imagine if this climber, having barely summited a modest hill with their current gear, contemplated tackling a towering mountain next. Would they proceed with the same equipment, or would they consult with seasoned professionals, seeking advice and re-evaluating their arsenal?

This is where Geoffrey A. Moore's concept of "crossing the chasm" becomes apt. Moore posits that for technology startups to transition from “early adopters” to a stage he coins “early majority”, they must significantly alter their strategies. He writes, "Crossing the Chasm" requires moving from the familiar territory of enthusiasts and visionaries to the pragmatic world of conservatives who represent the early majority. This leap is not merely geographical but strategic, demanding a profound rethinking of approach and assets. I’d argue the same philosophy should be applied to our content. 

As businesses aspire to scale upmarket, the question then becomes: Does your content upscale alongside your ambitions? Content that suffices for smaller prospects often lacks the depth, sophistication, and allure needed to engage and convert larger, more discerning audiences. It's about crafting messages that resonate on a deeper level, offering not just information but insights that speak to the specific challenges and aspirations of an upmarket clientele.

The journey from serving smaller prospects to engaging with larger entities mirrors the climber's transition between peaks. The chasm that lies between these two markets is vast and fraught with challenges. Yet, it's also brimming with opportunity for those willing to invest in the right tools and insights. Just as a climber reassesses their gear before a significant ascent, businesses must re-evaluate their content. The materials that got you here won't get you there.

Scaling upmarket demands more than just a rebranding or slight adjustments to your content strategy. It requires a fundamental overhaul of how you communicate value. Your content must not only inform but inspire, not just convince but compel. It must be meticulously tailored to resonate with the sophisticated needs and expectations of larger prospects.

As you contemplate scaling your business upmarket, consider whether your content is truly equipped for the journey ahead. Is it sufficiently compelling, insightful, and differentiated to capture the attention and loyalty of a more discerning audience? Or is it time to reinvent your approach, ensuring that your content—like the best-prepared climber—can scale new heights and bridge the chasm to upmarket success?

In this quest, the right content strategy isn't just an asset; it's an imperative. For those ready to make the leap, it's time to reassess, retool, and reimagine what your content can achieve. Only then can you confidently embark on the journey to scale new peaks and realize the full potential of your upmarket aspirations.