Why Good Operators Fail in Lean Online Businesses
Most founders treat operational hiring like a matching problem. Feel the pain, find the title, hire the person, hope it works. VA, OBM, integrator, operations manager — the titles blur together, the job descriptions overlap, and somehow every candidate promises they can "own your operations and give you your time back." Every day I get asked variations of the same question: why do my operational hires keep failing? In studying how lean online businesses actually run — and why good operators keep flaming out — I found the problem isn't the talent. It's what's missing underneath them.
The Industry Context
The hiring question only makes sense when you understand what operators in lean businesses are actually dealing with. The support landscape has a mentorship problem that no course or template can fix.
In a traditional company, an operations manager learns by watching a director. A director learns by watching a VP. There's a leadership layer above them modeling what good looks like, catching mistakes before they compound, teaching the nuances that don't exist in any certification program.
In a lean online business? There's the founder and there's the operator. That's it.
The operator is expected to figure it out. They've got courses, templates, communities, podcasts — unlimited information. But information isn't mentorship. Knowing what a P&L is supposed to look like isn't the same as having someone show you what this P&L is telling you about this business. Watching a workshop on team management isn't the same as having a leader in your corner when a contractor ghosts mid-launch.
The knowledge exists everywhere. The boots-on-the-ground guidance doesn't.
Which is exactly why good operators keep failing in lean businesses...
The Reactive Mode Trap
Even experienced operators — the ones who've been doing this for years — hit the same wall.
They're buried.
A good OBM or operations manager in a lean business is doing everything. Project management. Team coordination. Client onboarding. Tech troubleshooting. Vendor wrangling. Putting out fires. Keeping the trains running. When do they have time to step back and look at how the business is actually running? When do they audit the systems, spot the inefficiencies, think strategically about what needs to change?
They don't. They're in reactive mode — handling what's in front of them, triaging the urgent, surviving the week. This isn't a performance issue. It's a capacity issue. You can't run operations and improve operations at the same time. Not without burning out. Not without things slipping.
So the business keeps running, but it doesn't get better. The same problems recur. The same fires flare up. The founder wonders why they're paying for operational support but still feel like everything depends on them.
What Lean Teams Actually Need
The pattern I see in businesses that break through isn't that they found a unicorn hire. It's that they stopped expecting one person to be everything.
What actually works is structure with three layers:
Leadership. Someone who can see the whole picture. Set priorities. Make the strategic calls. Spot what's broken before it becomes a fire. This is the layer most lean businesses are missing entirely. It's also the layer that provides the mentorship operators are starving for.
Execution. Someone who can manage projects, coordinate the team, and make sure things actually get done. This is where most OBMs and ops managers live — and where they thrive when they have leadership above them and support below them.
Support. Someone who handles the daily tasks, the admin, the repeatable work that keeps everything moving. This frees up the executor to actually manage instead of drowning in details.
When all three layers work together, operators stop being set up to fail. They have someone above them to learn from, bounce ideas off, catch the things they can't see yet. They have support below them so they're not buried in task work. They can actually do the job they were hired for.
How This Compounds
The traditional model — hire one person, hope they stretch across all three levels — keeps founders stuck in a cycle. Hire, train, realize it's not working, part ways, repeat. Each cycle costs three to six months and thousands in lost productivity. Meanwhile, the operator burns out wondering why they couldn't make it work.
The structure model compounds differently.
When there's leadership in place, operators level up. They have someone to learn from. Someone to pressure-test their thinking. Someone to catch the gaps they can't see yet. That mentorship — the kind that barely exists in lean online businesses — becomes built into how the business runs.
When there's support in place, operators stop drowning. They can actually step back and improve the systems instead of just surviving them. Reactive mode becomes proactive mode.
When the structure is right, good people succeed. When it's not, even great people fail.
Why Most Businesses Can't Copy This
The math doesn't work for most lean businesses — and the constraint is instructive.
You can't afford a full-time COO, a full-time operations manager, and a full-time coordinator. So you try to hire one person and hope they can stretch across all three levels. They can't. Not well. Not sustainably.
A senior operator gets bored (and overpaid) doing support tasks. A junior coordinator gets overwhelmed trying to make leadership decisions. An OBM gets stuck in the middle, expected to be strategic but given no time or authority to actually lead.
The founders who break through aren't the ones who finally found the perfect hire. They're the ones who stopped trying to solve a structural problem with a personnel solution. They found a way to get all three layers without building a full team from scratch.
That's a fundamentally different approach to operational support — and it only works when the structure exists to hold it.
What This Means for You
If you've been cycling through operational hires and wondering what you're doing wrong — you're probably not doing anything wrong. You've been trying to solve the problem the way everyone says to solve it: find the right person.
But the right person can't succeed in the wrong structure.
Ask yourself: Does my operator have anyone to learn from — or are they figuring it out alone? Do they have time to improve the business — or are they just keeping it running? Am I expecting one person to cover leadership, execution, and support?
If the honest answer is yes to any of these, the problem isn't your hiring. It's what's underneath it.
Leadership. Execution. Support. Most lean businesses are trying to get all three from one hire. It doesn't work. At AbsoluteOps, we bring the full team dynamic — so your operators stop being set up to fail.
— Darci
