March 8, 2024
7 min read

Scaling Businesses Through Strategic Sales Expansion

Justin McCullough

Leveraging sales strategies to scale businesses

Running a business is all about solving problems. 

I co-founded my company to solve a problem I deeply understood. A problem I experienced firsthand. Some refer to this as "founder-problem fit." Many founders set out to do the same - solve their own problem. This deep knowledge of the initial problem is key to getting early traction.

But to scale, you inevitably need to bring on a team. That means transferring your specialized knowledge so others can solve that problem for customers also. This is the first chasm we experience – handing over your unique, intuitive grasp of the problem to sell and scale the solution. From founder-led sales to team-led sales, we trade domain expertise AND understanding for hired skill sets.

Yet something is lost when the baton gets passed. I've experienced this first hand several times. In one instance, I was handed the baton to stand-up a sales organization - to transition the firm from founder-led sales to team-led sales. The first questions I asked were:

"What does our customer know about the domain and the problem that I myself don't know?" 
“What is the insider problem that an outsider wouldn’t know?“

It was impossible for the founder to explain it to me. I had no real experience or understanding of the problem. I was simply a set of sales skills that was hired to sell a solution to anyone who would buy. We tried to mimic their understanding and descriptions of the situations we had heard, but we always lacked authenticity. Prospects can always tell. 

Effective approaches to moving up market

New team members can approximate and do their best to understand the problem, but they lack the visceral experience that sparked the founding insight. Fast forward as the business grows, and there is another chasm to cross. This chasm is crossed when moving upmarket. In fact, there’s an entire book written about it: Crossing the Chasm by Geoffrey Moore. When we move upmarket, both generalized & specialized capabilities across sales, marketing, and product dev now need to step in. To enable this, the leadership makes another trade-off.

Swapping rich, first-hand knowledge of the problem space for these crucial strategic and operational skills. This is very difficult. Many struggle. More fail. The cycle repeats at each inflection point. More distance grows from the original spark as priorities and perspectives shift. Revenue metrics may disguise a creeping disconnect from what made the solutions so compelling in the first place.

Here are some key questions all leaders should continually ask:

  • What problem(s) do we solve for customers today? How do we know we are still solving them? 
  • Are we missing the chance to build credibility by demonstrating our understanding of their problem? What effect does that have on our relationship?
  • Are we over-focused on what we’re creating & not what we’re solving for?
  • How might the problem have evolved as customers and markets change?
  • As new expertise enters the organization, how can we transfer the deep understanding of customer problems built up over time?

Paving the path to sustainable growth

Keeping your finger on the pulse of these evolving customer problems, even amidst tremendous growth and change, seems one promising way to build an organization that lasts. The solutions will change, but the commitment to understanding problems shouldn’t.

Written by
Justin McCullough