Strategists, Implementers, and COOs All Matter, but What Happens When You Hire the Wrong One First?
Over the years, I’ve worked with a lot of businesses that hired support roles expecting one thing, and getting something completely different.
- They brought in a VA, hoping for consistency.
- Hired an OBM, hoping for leadership.
- Worked with a COO, hoping for clarity.
- Sought out an “Implementer” hoping their big ideas would turn into for systems that scaled.
What they really needed wasn’t more hands and more hustle. They needed a systems thinker who could step back and see the whole picture. They needed someone to make sure the sales and marketing systems they built (or paid for) actually aligned with their business goals and real-world operations.
So for the sake of clarity, I’m going to break down the differences between these roles, explain where strategy fits in, and show you how to avoid the expensive mistake of hiring the right person in the wrong order. Because the truth is, even if you’ve already invested in systems, you may still be flying blind. And if you’re about to scale or make a key hire? That blind spot could cost you a lot more than just time.
Who’s Who in Your Back Office
If you’ve ever hired a VA, OBM, implementer, or even a COO and still felt like things weren’t quite clicking, you’re not alone. The titles might sound interchangeable. The job descriptions often blur. But these roles solve very different problems—and expecting one to do the job of another is where most people get stuck.
Here’s how they actually break down:
Virtual Assistant (VA)
A VA is there to take simple, straightforward tasks off your plate. They’re helpful when you know exactly what needs to be done and just need someone to do it. Think inbox management, uploading content, sending contracts, scheduling posts. They typically work best with clear step-by-step instructions or SOPs. In other words, they aren’t there to create systems, build strategy, or make decisions.
Good for: Handling repeatable tasks
Not for: Creating workflows, building dashboards, or fixing underperforming systems
Online Business Manager (OBM)
OBMs bring organization to the chaos. They help manage projects, timelines, and teams. They can keep things moving, keep people accountable, and make sure details don’t fall through the cracks. But they’re not systems thinkers—they typically rely on existing processes and direction. In other words, they’re there to manage what exists.
Good for: Operational project management
Not for: Diagnosing problems, optimizing marketing systems, or connecting tools across departments
Implementer
This term gets used in different ways. In corporate settings, an implementer might be the person turning OKRs into cross-team action.
In the online business world, Implementers specialize in tools. They know the tech, they can set it up, and they’ll follow a set process to a tee—if they’re given one. Implementers execute. They follow the strategy. They don’t create it. If you don’t already have a system mapped out, they’re likely to build what’s requested without questioning whether or not it’s the right thing to build.
Good for: Setting up single platforms like HighLevel, Dubsado, Asana, Zapier, ClickUp, etc.
Not for: Strategy, diagnosis, or big-picture decision-making
COO (or Fractional Ops Lead)
COOs build structure. They develop SOPs, workflows, and internal systems. They’re essential when your team is growing and you need internal clarity. But most COOs don’t come from a sales and marketing background. They don’t track funnel performance, optimize for inquiries, or tie systems to sales. Their focus is operations, not outcomes.
Good for: Internal operations and infrastructure
Not for: Marketing alignment, campaign performance, or lead pipeline reporting
What a Strategist Actually Does (That Most Teams Miss)
Strategist
A strategist comes in when everything should be working—but isn’t. They figure out what’s actually happening inside your systems, tools, and reporting—and what’s standing in the way of performance.
Strategists aren’t tied to a specific platform. They aren’t just there to brainstorm ideas with you. They assess the full marketing and sales ecosystem, identify bottlenecks, and help you prioritize what needs to be fixed, refined, or rebuilt before you scale.
They don’t just ask “what should we do?”—they ask “what’s actually working, and why?”
Good for: Diagnosing issues hidden in systems, mapping marketing performance to sales, aligning tools with business outcomes, preparing for sustainable growth
Not for: Task execution, internal project management, reactive support
Most of the business owners who come to me already have a team. A VA. Maybe an OBM or a fractional COO. Sometimes an implementer who set up their tools.
And on paper, everything looks like it should be working. The CRM is set up is paid for, workflows are in place, and the automations are active.
But behind the scenes there’s still underperformance and confusion.
- Leads aren’t converting
- Reporting is unreliable
- Repeatable tasks are still being done manually
- And no one can clearly say what’s actually driving revenue
Most of the time, it’s not a tech problem. It’s not even a team problem. It’s a systems problem. That’s where a strategist can help.
What Happens When You Hire the Wrong One First
Most business owners don’t get this wrong because they’re careless. They get it wrong because the job descriptions are vague, the titles overlap, and the urgency to “just get help” outweighs the time it takes to define what kind of help they actually need.
But hiring the right person in the wrong sequence doesn’t just slow you down—it creates expensive, hidden problems that usually don’t surface until you’re already scaling.
If You Hire a COO or Implementer Before a Strategist:
On the surface, everything looks like it’s in motion. You’ve got the CRM. You’ve got the automations. You’ve got the SOPs that show who’s responsible for what.
But under the surface, no one’s quite sure if the pieces are talking to each other. Or if the way things were set up actually reflects how your business works now. Or if the data in the dashboard matches what’s really happening on the ground.
So when performance lags, no one knows where to look. The sales team blames the leads. Marketing blames the funnel. And leadership is left trying to make decisions based on reports they don’t fully trust.
By the time you realize something’s off, you’re already deep into hiring, training, and handing things off. Which means now you’re not just building—you’re backtracking.
If You Hire a VA or OBM Before a Strategist:
Things start to feel more manageable. The inbox is under control. Projects are moving forward. You finally have help—and on the surface, things look more organized.
But the deeper questions still haven’t been answered. You’re delegating tasks inside systems that may not be working. The team is busy, but no one knows if the work is actually moving the needle.
This is how businesses stay stuck in maintenance mode—overfunctioning and under-optimizing.
If You Hire a Strategist First:
Here’s the reality: things may seem to move slower at the beginning—but for the right reasons.
Instead of rushing to set up tools, your strategist will work with you to understand your business from the inside out. A good strategist understands that not every business or market is the same. They’re able to take your big-picture business goals and map them to your systems in order to find what’s working well that can be optimized and what gaps need to be addressed immediately.
It doesn’t mean you won’t need a new team member, like a VA , COO, or OBM. It just means you avoid layering new people or platforms on top of an unstable foundation. New hires get supported by the system, not confused by it.
Didn’t Hire a Strategist First? You’re Not Behind.
If you’ve already hired a VA, OBM, or COO before bringing in a strategist, you’re not wrong. You were solving the problem you could see. Chances are, you’ve made real progress—SOPs are in place, tools are set up, and things look more organized than they used to.
But if performance is still inconsistent, if you’re not confident in what’s working, or if your systems feel like they’re adding work instead of saving time, that’s not failure. It’s just the next phase.
This is where a strategist becomes essential. They can optimize strong systems further and to make sure everything is working the way it’s intended to.
How to Know If You Need a Strategist
Sometimes things look fine on the surface—SOPs are in place, tools are set up, and the team is following the plan. But behind the scenes, there’s friction. Questions aren’t getting answered. Results are inconsistent. And the more you try to push forward, the more resistance you meet.
That’s usually the moment a strategist becomes necessary.
You might be there if:
- You’ve invested in systems but aren’t confident they’re doing what they’re supposed to
- Your team is doing the work, but performance still lags
- Reporting exists, but no one’s using it to make decisions
- You’re about to make a key hire and don’t want them walking into a mess
- You feel like you’re scaling something that hasn’t really been stress-tested
You might not need a strategist yet if you’re still in the early stages—no systems, no team, and nothing to audit. Or if what you need most right now is implementation and task execution.
But if you’re somewhere in the middle—building, growing, trying to make smarter use of the infrastructure you already have—a strategist can save you time, money, and more backtracking down the line.
Strategic Moves with Mountainside Media
Most of our clients aren’t starting from scratch. They’ve already spent money on tools, set up systems, maybe even hired a team. But they’re still circling the same problems: inconsistent performance, unreliable reporting, and a growing list of questions no one can answer clearly.
What they need at that point i a strategic pause to look at whether what’s been built can actually do its job.
That’s where we come in.
At Mountainside Media, we help growth-stage service businesses stabilize what they’ve already built—so their systems can scale, their team can make smarter decisions, and their marketing efforts aren’t wasted on guesswork.
We do this through focused services like analytics, paid ads, market research, and smart, intentional uses of AI. But the real work happens in how we assess what’s actually happening inside your business—and what needs to change if you’re going to keep moving forward without burning out your team, your time, or your budget.
If you’re realizing the next step isn’t more effort—it’s better structure—you can learn more about our services and how we work.
