Your Best Strategist and Your Best Ops Hire Are Rarely the Same Person
You’ve built a team of people who kill it at delivering — managing timelines, keeping clients happy, shipping work on time. But when it comes to thinking ahead, building the playbook, or making strategic calls that shape the direction of the agency… you’re still doing all of that yourself.
Sound familiar? You’re not alone. And the reason it keeps happening is because most agencies conflate two fundamentally different skill sets into one hire.
The Strategy Brain vs. The Operations Brain
A great strategist sees the whole board. They can sit in a client meeting, hear what’s being said (and what’s not being said), and come back with a point of view about where the real opportunity is. They think in terms of positioning, differentiation, narrative. They’re comfortable with ambiguity and can turn messy inputs into a clear direction.
A great ops person sees the machine. They can take that strategic direction and break it into workstreams, assign ownership, set timelines, build the system that makes it repeatable. They think in terms of capacity, efficiency, and risk mitigation. They turn direction into execution.
Both are essential. But they require fundamentally different wiring — and trying to find both in one person is how you end up with either a strategist who can’t ship or an executor who can’t think past next week.
Where Agencies Go Wrong
The most common mistake I see is agencies hiring a Director of Strategy or VP of Client Services and expecting them to be both. They need someone to set the direction AND run the team. So they write a job description that’s half visionary, half project manager, and wonder why none of the candidates feel right.
Or worse — they hire a strong operator and then get frustrated when that person doesn’t bring strategic ideas to the table. The operator is doing exactly what they’re wired to do: keeping things running. But the agency needed someone to reimagine what “things” should be running in the first place.
How to Think About This
If you’re a sub-50 person agency, you probably can’t afford to hire both a dedicated strategist and a dedicated ops lead. That’s fine. But you need to be honest about which one you’re actually hiring and build a plan to cover the other.
If you hire for strategy: Pair them with a strong project management layer (even if it’s a tool + a junior PM) so the strategic thinking actually gets implemented. Don’t let your strategist get buried in execution — that’s the fastest way to burn out your most expensive hire.
If you hire for ops: Keep the strategic thinking with leadership for now, but create structured moments (quarterly planning, client reviews, pitch development) where strategic input gets formalized. Don’t expect your ops person to spontaneously generate strategy — give them a framework.
If you need both and can only hire one: Hire the ops person and bring strategy in fractionally. A fractional strategist or advisor working 10-15 hours a week can set direction while a full-time ops hire makes sure it actually happens. This is almost always more cost-effective than trying to find a unicorn.
The Leadership Trap
Here’s the part nobody talks about: a lot of agency founders keep strategy close because they enjoy it. It’s the fun part. It’s where the creative energy lives. And letting go of it feels like losing identity.
But if you’re the only strategic thinker in the building, you’re also the bottleneck. Every new business opportunity, every client pivot, every positioning conversation flows through you. And that means your agency can only grow as fast as your personal bandwidth allows.
Separating strategy from operations isn’t just an org design exercise. It’s a growth decision. And the sooner you make it intentionally, the sooner you stop being the ceiling on your own business.