Field Notes · Leadership

Part 2: The Founder Ceiling.

12 Jun 2026·Four-minute read·By Sam Wood

To recap:

  1. You know what you're spending your day doing because you tracked it
  2. You've decided what your role should be in the agency
  3. You've used steps 1 and 2 to identify the opportunities for someone else to take some work off your plate

The hires that make the biggest difference

In my experience, once you've been through this process, the gaps tend to fall into a few buckets.

Operational leadership

Someone who owns the work behind the work. Keeping the systems running, making sure invoices go out on time, the project management side of things, coordinating everything that needs to happen for the agency to function properly.

This could be an ops manager, an office manager, or at a certain size, a GM covering a lot of these responsibilities. A lot of it is also good fodder for contractors or outsourcing. But you do need to stay across it.

Client service leadership

If you're constantly being dragged back into client meetings simply because the relationship is with you, this is the role to fix it. A senior account manager, a head of client service, someone who can own those relationships day-to-day. Done well, this isn't just a way for you to move some emails on to someone else - these people can be KPI'd on client retention and growth. It can be a revenue-generating role if you set it up as such.

Project management

Particularly if you're running a dev agency or handling complex, multi-stage projects. A good project manager and a good client service person are often very different people. Great PMs are rigid, relentless, and will keep things moving regardless of how inconvenient that is. Client service people sometimes tend to be more focused on making the client ‘happy’ (I’m not going into whether this is actually the role or not - this is just what I’ve observed as common). Sometimes the same person can do both. Often they can't.

Marketing

Agencies are, broadly speaking, terrible at marketing themselves. If you're reading this, you’ve probably heard me say that before.

This doesn't need to be a full-time hire though. In fact, it probably shouldn't be. Two days a week of a senior marketer who would otherwise cost $150k+ a year will get you substantially more value than a junior five days a week. Supplement that with specific contractors for execution.

Having someone whose entire job is tied to your agency's marketing metrics means those metrics actually get focused on. As a founder, you will always push marketing aside when something more urgent appears. A dedicated person is much less likely to do so.

New business support

I want to be clear here: bringing in an experienced senior salesperson as a silver bullet almost never works in agencies.

I've heard versions of this story more than ten times now. Someone brings in a senior BD person at $150k-$170k, 12-18 months later it hasn't worked, and between salary, recruitment fees, and exit costs, you're looking at somewhere between $200k-$250k and you're no further ahead.

The profile that tends to work instead is someone earlier in their career, maybe two to three years in a similar agency environment, who has a genuine commercial mindset and a real understanding of the product - ie someone you can train up. That investment pays off, but it's a medium-term investment, not a quick fix.

A quick note on org design

This is obviously a huge topic in and of itself. The below is what I had time to cover in the webinar.

Seven direct reports is roughly the maximum before your entire job becomes managing people and nothing else. You can't scale a flat structure indefinitely. At some point you need managers, layers, structure. That means performance reviews, performance management, all the things that come with it. Starting to think about this before you need it is dramatically better than reacting to it.

Reactive hiring in general is almost always worse than not hiring. If someone resigns and you hire the first CV that lands on your desk, you're probably making things worse. There's the direct cost, the opportunity cost of having the wrong person in the seat, and the structural damage of someone who doesn't fit the role you actually need filled.

The right organisation design doesn't exist as some perfect final state. What matters is the thinking that goes into it, and revisiting it regularly.

Cheers, Sam

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