Herringbone Digital Blog

This is the third post in my series on the four strategic paths available to agency owners.

In my previous post, I shared thoughts on the pros and cons of staying the course. Today, let’s dive into growing organically—a path that many agency owners instinctively choose.

Nearly every agency I speak with is brimming with optimism:

“We’re going to double revenue this year—we just hired a sales team / launched a new service / signed a major partnership.”

And sometimes, that optimism is justified. Especially for smaller agencies, there is real potential to double or even triple in size quickly. One of the biggest advantages of organic growth? You get to pursue your vision on your own terms—no external investors, no M&A complications. Just you, your team, and your ability to execute.

But there are real challenges too.

1. Scaling gets exponentially harder. Going from $1M to $2M is very different from going $2M to $4M. The systems, team, and operations need to evolve—fast.
   
2. The industry is shifting rapidly. AI, evolving client expectations, and changing consumer behavior mean the game is being rewritten in real time. What worked last year might not work next quarter.
   

I’m not saying organic growth is the wrong move. In fact, for many, it’s absolutely the right one. But optimism needs to be balanced with realism. Growth is never guaranteed—and the risks are real.

If you’re committed to this path, do it with eyes wide open. Mitigate the risks. And don’t forget—there are three other paths worth exploring.

In the previous blog post, I shared the four strategic paths available to agency owners:

1. Stay the Course
   
2. Grow Organically
   
3. Grow Through Acquisition
   
4. Sell the Agency
   

In this post, I wanted to explore the first option: staying the course.

For some agency owners, the status quo is a comfortable — and even attractive — place to be. The team is humming, clients are happy, the income is solid, and there’s minimal stress. When things are working, the instinct is often: “Why rock the boat?”

But here’s the challenge with maintaining the status quo — the world doesn’t stand still.
Search engines evolve. Competitors emerge. Client needs shift. And AI? We’re just scratching the surface of how transformative it will be in the agency world.

So here’s my take:
If you’re a few years from retirement, deeply niched, and flying under the radar — sticking with the status quo might be perfectly reasonable.

But if you’re earlier in your career or not willing to “settle down”, this strategy could leave you vulnerable. Complacency is not a moat.

What are the options for owners of digital marketing agencies?

That’s a question I’m hearing more and more from agency owners. On one hand, there are some many opportunities to invest and grow the agency. On the other hand, uncertainty around the economy, constant changes by Google and of course AI are real stressors for owners.

At it’s core, there are 4 options for owners of digital marketing agencies:

1. Stay The Course – for many agency owners, they have found the perfect balance between clients, workload and income. They may lose a customer, gain a customer, lose a team member, hire a team member. But for the most part, things are great and they will remain great for the foreseeable future

2. Grow Organically – these agency want to / need to grow and are committed to doing that via organic means i.e. just winning more customers than they lose.

3. Grow Through Acquisitions – a great way to expand into different product offerings, different geographies or just gain scale

4. Sell – exit altogether, or be bought to be part of something bigger and access resources, capital, talent to help take the agency to the next level.

Over the course of the next few blog posts, I’ll dive into each of these, examining the pros and cons of each. At the end of it, my hope is that agency owners, wherever they are in their journey, will have a much clearer sense of the path forward.